WEBVTT

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Welcome back to the Deep Dive. Today, we aren't

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just looking at a business case study. I think

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it's fair to say we are performing a full -scale

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autopsy on a giant. A giant that for a very,

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very long time felt... Well, it felt immortal,

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didn't it? It really did. OK, so let's just unpack

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this for a second. I want you to look at the

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date on your phone or your calendar, whatever

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you use. It is February 14th, 2026. Valentine's

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Day. Exactly. Valentine's Day. Now, I want you

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to imagine it's Valentine's Day back in, say,

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1994. You need to grab a last minute box of chocolates,

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maybe a cheesy card. maybe a blender because

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you're a practical romantic, I don't know. You

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had a really, really easy option. You could just

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drive to one of the nearly two and a half thousand

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locations of a specific retailer. A retailer

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that was at that exact moment, one of the largest

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corporate entities on the entire planet. We are

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talking a force about Kmart. And I think the

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scale of Kmart in 1994 is, it's actually hard

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to overstate. Oh, completely. They operated 2

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,486 stores globally. They were the original

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category killer. They really defined the whole

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concept of the discount department store long

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before Sam Walton was a household name. And that

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right there, that is the hook for today's mystery.

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Because here we are in February 2026, and that

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empire has, it's completely evaporated. Vanished.

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And I don't just mean it's struggling or downsizing.

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I mean, for all intents and purposes, it is gone.

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It's a vanishing act of historical proportions.

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If you pull up a map. of the mainland United

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States right now, today, and you search for a

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Kmart, you will find exactly one pin on that

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map. One, just one, in the entire lower 48 states.

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And even that one, which is down in Miami, Florida,

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I mean, it's barely a Kmart. It has an asterisk

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next to its name the size of a billboard, which

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I'm sure we'll get to later. Oh, we will. But

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aside from that one, that single anomaly. The

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brand has been just wiped off the continent.

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You literally have to get on a plane and fly

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to Guam or the U .S. Virgin Islands just to see

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that big red K on a storefront. So the mission

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for this deep dive is to answer the question,

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how? How does that happen? We have a massive

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stack of sources in front of us. We've got corporate

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history records going all the way back to 1899.

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We have bankruptcy filings that. I'm not kidding.

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Read like a Shakespearean tragedy. Right. Store

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closure timelines, operational reports. We need

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to figure out how a company that had such a massive

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head start on Walmart, a company that was a cultural

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icon with the blue light special, how it managed

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to collapse so completely. It's really a story

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about the tension between innovation and stagnation.

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It's about an identity crisis that spanned decades.

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It's also about a disastrous merger that. I think

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I remember one financial analyst at the time

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described it as two drowning people trying to

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save each other by grabbing onto each other.

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That's a perfect description. And crucially,

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it's about specific, almost granular strategic

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failures. Failures with technology, with supply

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chains, things that sealed their fate 20 years

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before the end was even in sight. Well, let's

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start at the foundation then, because I think

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there's this common assumption that Kmart just

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sort of popped up fully formed in the suburbs

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in the 1970s. But the roots go way, way back,

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don't they? Much, much further back. To understand

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the fall, you really have to respect the rise.

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And the story starts in the late 19th century.

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We're talking about a man named Sebastian Sparing

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Krez. S .S. Krez. It sounds like the name of

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a ship, like a big steamliner. And he was a force

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of nature in a way. He was a traveling salesman

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originally. And get this, he actually sold tinware.

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to Frank Winfield Woolworth. Wait, wait. As in

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the Woolworth? The guy who basically invented

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the five and dime store. The very same. Yeah.

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Kredge was selling to the pioneer who invented

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the entire category. So he saw firsthand what

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Woolworth was doing, this model of high volume,

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low prices. And he thought, you know, I want

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a piece of that action. So he learned from the

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master. He did. So in 1897, Kredge takes $6 ,700,

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which was his entire life savings from being

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on the road, and he invests it into a store in

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Memphis, Tennessee with a partner. Wow. $6 ,700.

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And by 1899, he's traded his share in that store

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for full ownership of a store in Detroit. And

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that Detroit store. That is really the true beginning

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of the S .S. Kresch company. And just to be clear,

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this wasn't a Kmart yet. This was a classic variety

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store. Exactly. It was a five and dime. The whole

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gimmick was the price point. Everything was cheap,

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five or ten cents. In fact, during World War

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I, when inflation was really hitting hard, Kresch

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experimented with raising the price limit in

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his stores all the way up to one dollar. And

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that was seen as like a huge innovation at the

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time. A massive deal. But the company was a monster

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success. By 1912, they incorporated with 85 stores.

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By 1924, Kredge himself was worth about $375

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million. Which is what in today's money? Billions.

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Billions and billions. They survived the Great

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Depression. They survived two world wars. They

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were a blue chip staple of the American economy.

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But the pivot, the moment that really, really

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matters for our deep dive. that comes after World

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War II, the entire world changed and where people

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lived changed. Exactly right. The great migration

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to the suburbs. In the late 40s and 50s, the

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Kretsch executives, they were looking at the

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data. People were leaving the crowded city centers

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where all the Kretsch variety stores were. They

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were moving out to places like Levittown, these

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sprawling new communities. Right. And shopping

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patterns were shifting. It went from walking

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to the corner store to driving the family car

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to the new shopping center. And there was an

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executive at Kredge named Harry Cunningham who

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saw the writing on the wall. He knew they had

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to change. Cunningham is really the father of

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the modern Kmart, isn't he? He's the visionary

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in this part of the story. He absolutely is.

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In 1961, Cunningham went on what you could call

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a reconnaissance mission. He toured a store called

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Ann and Hope. in Rhode Island. And in Hope. I've

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never even heard of that. Most people today haven't.

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But they were the true pioneers of the discount

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department store model. Centralized checkouts,

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shopping carts, self -service. All the things

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we take for granted now, they were doing it first.

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Okay, so Cunningham goes there to take notes.

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He does. And here's where we get one of the great

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historical coincidences. One of the great what

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-ifs of retail history. Go on. In that same year,

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1961, A guy from Arkansas named Sam Walton, the

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founder of Walmart, also visited that exact same

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Anne and Hope store in Rhode Island. No way.

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At the same time. Roughly the same time. They

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were both walking the aisles of the same store,

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taking notes on the same business model. They

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were literally drinking from the same well of

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inspiration. That is just wild. That's a movie

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scene. It is. But here's the crucial difference.

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Cunningham had the massive resources of the S

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.S. Crush company behind him. He didn't have

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to scrape for loans and mortgage his house like

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Sam Walton did. Krez had the capital to move

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fast. And they moved very fast. On January 25,

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1962, the S .S. Kredge Company opened the very

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first store that had the name Kmart on it. It

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was in San Fernando, California. Now, was that

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the big 80 ,000 square foot box store that we

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all remember? Actually, no. And this is an interesting

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little footnote. Kredge called it a Bantam Kmart.

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It was smaller, only about 27 ,000 square feet.

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It was actually supposed to be a traditional

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Kredge store until very late in the planning

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process when they decided to test out the new

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branding. So it was like a prototype. A proof

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of concept. But just a few months later, on March

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1st, 1962, they opened the first ground -up,

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full -sized, purpose -built Kmart in Garden City,

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Michigan. How big was that one? 80 ,000 square

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feet. This was the real deal. This was the template

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for the thousands of stores that would follow.

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And that year, 1962... We have to talk about

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that year. It keeps coming up in business textbooks

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for a very good reason. It's what people call

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the class of 62. It's incredible. In that single

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year, you had the founding of Kmart, the founding

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of Walmart, and the founding of Target. All three

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retail giants launched within months of each

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other. But Kmart was the big brother in that

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class, right? They were the ones with the advantage.

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Oh, absolutely. Kmart was the rich kid on the

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block. They had the capital. They had the existing

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supply lines. They had the real estate expertise

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from the Krezh empire. They opened 17 more stores

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just in 1962 alone. And Walmart at that point

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was just a handful of stores in Arkansas? A tiny

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speck in Arkansas by comparison. Kmart had this

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huge head start. And by 1977, the business was

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so dominant that the company officially changed

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its name from S .S. Krezh Co. to Kmart Corporation.

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They were the force. They were the ones putting

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everyone else out of business. And that dominance,

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that brings us right into the golden era. The

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time when Kmart wasn't just a store, it was a

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cultural phenomenon. We have to talk about the

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blue light. We have to. The blue light special.

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It was introduced in 1965, and it is arguably

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one of the most famous, most effective marketing

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tactics in the entire history of retail. Okay,

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so for our younger listeners who might strictly

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be online shoppers who've never experienced this,

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paint the picture for us. How did this actually

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work physically inside the store? It was so brilliantly

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low tech, but psychologically. It was genius.

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A store employee would literally wheel a cart,

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like a tall metal stand on wheels, with a rotating

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blue police -style light on top. Just a regular

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plug -in light? Yep. They'd wheel it to a specific

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aisle, plug it into an outlet, and the light

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would start spinning. And then a voice would

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come over the store's PA system, and it always

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started the same way. Attention, Kmart shoppers.

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Chills. I can still hear that voice. Yeah. And

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it was a flash sale, right? A flash sale. For

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the next 15 minutes only, in aisle four, men's

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tube socks are 50 % off. Or motor oil. Or blenders.

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Or whatever it was. So it started as just a way

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to get rid of inventory they had too much of.

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That was the original idea. It was a mechanism

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to clear out slow -moving merchandise. If you

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had way too much stock of something, you just

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flash the blue light on it and clear the shelf.

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But it became so much more than that. It became

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a pop culture touchstone. It created this sense

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of urgency. an event happening it totally did

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it gamified shopping before gamification was

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even a buzzword you might be on the other side

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of the store but you'd hear that announcement

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and you would literally run over just to see

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what was happening you didn't want to miss out

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it was a classic impulse by a driver exactly

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it created a collective experience in the store

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everyone would converge on that blue light It

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was like a little party in aisle seven. It worked

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so, so well that Kmart used it aggressively for

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nearly 30 years. It was their signature. And

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that marketing engine, it just fueled this incredible,

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relentless growth. Throughout the 70s, Kmart

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was just ruthless. They were the apex predator

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of discount retail. They put a ton of regional

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competitors out of business. Chains like Zare,

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Ames, Hills. Kmart just rolled into town and

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crushed them. And the numbers just kept climbing.

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Oh, yeah. By 1981, they opened their 2000th store.

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And by 1990, they were the second largest retailer

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in the United States, second only to Sears. Which

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is so ironic considering what happens later in

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the story. But here, right here at their peak,

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this is where the cracks really start to form.

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In the 80s and 90s, while they were sitting on

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top of the world, Kmart completely lost focus.

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They absolutely did. They fell into what I call

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the diversification trap. Instead of pouring

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all their resources, all their brainpower into

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making the Kmart stores better, cleaner, and

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more efficient, the leadership, they kind of

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got bored with just selling discounted goods.

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They wanted to build an empire of brands. They

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went on a shopping spree. A massive one. It's

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almost hard to believe the list of companies

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they bought. They bought the bookstore chain

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Walden Books. Okay, I remember that. Then they

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bought Borders and merged them. They bought a

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home improvement chain called Builder's Square

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to compete with Home Depot. Right, Builder's

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Square. They bought Sports Authority in 1990.

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They bought Payless Drugs in 1985. They bought

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OfficeMax in 1991. I think they owned OfficeMax,

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too. I had no idea. It's like they were trying

00:11:59.669 --> 00:12:02.110
to be everything to everyone all at once. They

00:12:02.110 --> 00:12:04.889
were building a conglomerate. And the major consequence

00:12:04.889 --> 00:12:07.769
of that was that the corporate focus. the attention

00:12:07.769 --> 00:12:10.129
of the C -suite. It shifted away from the core

00:12:10.129 --> 00:12:12.850
business. While the top executives were busy

00:12:12.850 --> 00:12:14.710
figuring out how to manage a bookstore chain

00:12:14.710 --> 00:12:17.690
and a sporting goods chain, the actual Kmart

00:12:17.690 --> 00:12:20.169
stores, the engine of their profit, started to

00:12:20.169 --> 00:12:22.830
suffer from serious neglect. And meanwhile, down

00:12:22.830 --> 00:12:25.230
in Arkansas, Sam Walton is doing the exact opposite.

00:12:25.309 --> 00:12:28.490
He isn't buying bookstores. No, he's obsessing

00:12:28.490 --> 00:12:31.289
over one thing and one thing only, supply chains.

00:12:32.009 --> 00:12:34.730
And that brings us to part three, the stumble.

00:12:35.259 --> 00:12:38.259
The 1990s are really where the war was lost,

00:12:38.399 --> 00:12:40.519
even if the company managed to survive for another

00:12:40.519 --> 00:12:42.620
30 years. And it starts with a huge psychological

00:12:42.620 --> 00:12:45.779
blow. It does. In November 1990, Walmart officially

00:12:45.779 --> 00:12:48.159
surpassed Kmart in size to become the number

00:12:48.159 --> 00:12:50.120
one retailer in America. That must have been

00:12:50.120 --> 00:12:52.679
a massive shock to the ego in Troy, Michigan

00:12:52.679 --> 00:12:55.759
at Kmart headquarters. It had to be. But the

00:12:55.759 --> 00:12:57.639
reasons for it were structural and they were

00:12:57.639 --> 00:13:00.009
technological. This is the part of the story

00:13:00.009 --> 00:13:01.789
that isn't as sexy as the blue light special,

00:13:02.029 --> 00:13:04.850
but it is the absolute core reason why Kmart

00:13:04.850 --> 00:13:07.669
died and Walmart lived. It all comes down to

00:13:07.669 --> 00:13:11.090
data. Explain that. How did data, or a lack of

00:13:11.090 --> 00:13:14.070
it, kill Kmart? Well, starting in the late 80s,

00:13:14.090 --> 00:13:17.830
Walmart and Target invested billions with a B.

00:13:18.299 --> 00:13:21.580
into computer systems, into barcodes, into satellite

00:13:21.580 --> 00:13:23.679
tracking for their truck fleets. They built this

00:13:23.679 --> 00:13:25.460
incredible high -tech system where they knew

00:13:25.460 --> 00:13:28.320
exactly what was on every single shelf in every

00:13:28.320 --> 00:13:31.159
single store in real time. So if a tube of toothpaste

00:13:31.159 --> 00:13:34.480
sold in Kansas at 2 .0 p .m. The central warehouse

00:13:34.480 --> 00:13:37.159
knew about it instantly, and a replacement was

00:13:37.159 --> 00:13:39.139
already queued up to be shipped that night. It

00:13:39.139 --> 00:13:41.799
was called just -in -time inventory. It was revolutionary.

00:13:42.519 --> 00:13:44.460
Okay, so that's Walmart. What was Kmart doing?

00:13:44.720 --> 00:13:47.200
Kmart did not invest. It's as simple as that.

00:13:47.470 --> 00:13:49.830
The board prioritized paying high dividends to

00:13:49.830 --> 00:13:51.830
their shareholders. They took the short -term

00:13:51.830 --> 00:13:54.629
profit, the easy money, over the long -term expensive

00:13:54.629 --> 00:13:57.149
and difficult infrastructure investment. So what

00:13:57.149 --> 00:13:58.809
did that mean in practice? Their supply chain

00:13:58.809 --> 00:14:01.850
was just old. It was antiquated. This meant they

00:14:01.850 --> 00:14:04.049
often had shelves that were either empty of the

00:14:04.049 --> 00:14:06.889
stuff people actually wanted to buy or they were

00:14:06.889 --> 00:14:09.730
overflowing with stuff that nobody wanted. Their

00:14:09.730 --> 00:14:11.629
distribution costs were higher. They couldn't

00:14:11.629 --> 00:14:13.750
compete with Walmart on price because their whole

00:14:13.750 --> 00:14:16.639
back -end system was so inefficient. So while

00:14:16.639 --> 00:14:19.620
Walmart is becoming this finely tuned, data -driven

00:14:19.620 --> 00:14:23.539
machine, Kmart is essentially flying blind. That's

00:14:23.539 --> 00:14:25.600
a great way to put it. And because they were

00:14:25.600 --> 00:14:27.759
losing ground, they started to have this massive

00:14:27.759 --> 00:14:29.840
identity crisis. They kept trying to rebrand,

00:14:29.940 --> 00:14:31.860
just hoping a new coat of paint would somehow

00:14:31.860 --> 00:14:34.919
fix the rotting foundation. Oh, I remember this

00:14:34.919 --> 00:14:37.360
era so well. The logo just kept changing, didn't

00:14:37.360 --> 00:14:40.039
it? It was constant. In 1990, they ditched that

00:14:40.039 --> 00:14:42.759
classic turquoise italic K and went to the big

00:14:42.759 --> 00:14:45.360
red block letter K with the word March written

00:14:45.360 --> 00:14:47.679
inside it. And one we all know. Right. But then

00:14:47.679 --> 00:14:48.960
they started messing with the store formats.

00:14:49.279 --> 00:14:52.000
They launched the Super Kmart Center in 1991.

00:14:52.639 --> 00:14:55.379
That was their big attempt to compete directly

00:14:55.379 --> 00:14:58.080
with Walmart super centers. They added full grocery

00:14:58.080 --> 00:15:01.059
stores, bakeries, delis, seafood counters, the

00:15:01.059 --> 00:15:03.659
works. I remember the Super Kmarts. They were

00:15:03.659 --> 00:15:06.600
absolutely huge, cavernous. They were massive.

00:15:07.200 --> 00:15:10.120
But then, just a few years later, they pivoted

00:15:10.120 --> 00:15:13.980
again. In 1997, they launched a new concept called

00:15:13.980 --> 00:15:17.120
Big Kmart. Okay, Big Kmart. What was the difference,

00:15:17.200 --> 00:15:18.820
really? It sounds almost the same. Well, Big

00:15:18.820 --> 00:15:21.299
Kmart was supposed to be brighter with wider

00:15:21.299 --> 00:15:24.740
aisles. The focus was more on home fashion and

00:15:24.740 --> 00:15:27.899
children's apparel, and they had a big consumable

00:15:27.899 --> 00:15:30.940
section called the pantry. By the year 2000,

00:15:31.240 --> 00:15:33.960
they had converted something like 1 ,900 of their

00:15:33.960 --> 00:15:36.440
stores to the big Kmart format. It just feels

00:15:36.440 --> 00:15:38.519
like flailing. It feels desperate. Like maybe

00:15:38.519 --> 00:15:40.679
if we call it big, people will come back. It

00:15:40.679 --> 00:15:42.639
was absolutely flailing. They even had another

00:15:42.639 --> 00:15:45.779
really short -lived concept in 1995 called Today's

00:15:45.779 --> 00:15:47.940
Kmart. They were just trying to find a format.

00:15:48.299 --> 00:15:50.440
any format that would stick, but they weren't

00:15:50.440 --> 00:15:52.879
fixing the underlying issue, which was that the

00:15:52.879 --> 00:15:54.980
stores were often getting dirty, the inventory

00:15:54.980 --> 00:15:57.879
was completely unreliable, and the customer service

00:15:57.879 --> 00:16:00.519
was lagging way behind Walmart and Target. You

00:16:00.519 --> 00:16:02.399
can change the sign out front as many times as

00:16:02.399 --> 00:16:04.639
you want, but if the floor is dirty and the shelves

00:16:04.639 --> 00:16:07.220
are empty, the customer's not coming back. And

00:16:07.220 --> 00:16:12.299
all of this, this downward spiral, it leads directly

00:16:12.299 --> 00:16:15.960
to the first big crash. It does. January 22,

00:16:16.220 --> 00:16:19.539
2002. Kmart files for Chapter 11 bankruptcy.

00:16:20.379 --> 00:16:22.539
At the time, it was the largest retail bankruptcy

00:16:22.539 --> 00:16:24.679
in American history. And this wasn't just a,

00:16:24.720 --> 00:16:26.500
well, we had a few bad sales quarters kind of

00:16:26.500 --> 00:16:28.200
bankruptcy. There was a lot of scandal involved

00:16:28.200 --> 00:16:30.360
with this one. Oh, yes. The leadership at the

00:16:30.360 --> 00:16:33.100
time, the chairman, a guy named Chuck Conaway,

00:16:33.179 --> 00:16:35.279
and the president, Mark Schwartz, they faced

00:16:35.279 --> 00:16:38.159
some very serious accusations. Like what? They

00:16:38.159 --> 00:16:40.120
were accused of deliberately misleading shareholders

00:16:40.120 --> 00:16:43.679
about the company's financial crisis. And optics

00:16:43.679 --> 00:16:46.570
were just... They were terrible. There were all

00:16:46.570 --> 00:16:48.129
these reports coming out that they were spending

00:16:48.129 --> 00:16:50.710
company money on private airplanes, on expensive

00:16:50.710 --> 00:16:53.889
houses, on boats, all while the ship was literally

00:16:53.889 --> 00:16:56.409
sinking beneath them. That is the absolute classic

00:16:56.409 --> 00:16:59.289
corporate villain story right there. It is. And

00:16:59.289 --> 00:17:01.370
the fallout from the bankruptcy was just brutal.

00:17:01.909 --> 00:17:04.529
They closed over 300 stores almost immediately.

00:17:04.890 --> 00:17:07.230
They pulled out of the entire state of Alaska.

00:17:07.630 --> 00:17:10.450
34 ,000 workers lost their jobs. A huge number.

00:17:10.849 --> 00:17:13.410
And... In a move that was just so symbolic of

00:17:13.410 --> 00:17:16.210
their confusion, they officially discontinued

00:17:16.210 --> 00:17:19.049
the blue light special. They tried to modernize

00:17:19.049 --> 00:17:21.390
by killing the one unique beloved thing that

00:17:21.390 --> 00:17:23.589
made them famous in the first place. So they

00:17:23.589 --> 00:17:26.269
emerge from bankruptcy, but everything is different

00:17:26.269 --> 00:17:29.390
now. The company is vulnerable. And this is where

00:17:29.390 --> 00:17:31.650
a new player enters the game. This is where Eddie

00:17:31.650 --> 00:17:34.890
Lampert comes in. This is part four. The merger

00:17:34.890 --> 00:17:37.039
in the Lampert era. And this is probably the

00:17:37.039 --> 00:17:39.579
most controversial, most debated chapter in the

00:17:39.579 --> 00:17:42.119
entire history of modern retail. So what happened?

00:17:42.240 --> 00:17:44.980
While Kmart was in bankruptcy, a hedge fund called

00:17:44.980 --> 00:17:47.660
ESL Investments, which was run by Edward Lampert,

00:17:47.779 --> 00:17:50.720
started buying up a huge chunk of Kmart's corporate

00:17:50.720 --> 00:17:53.240
debt for pennies on the dollar. So he wasn't

00:17:53.240 --> 00:17:55.019
buying stock. He was buying the debt. He was

00:17:55.019 --> 00:17:57.819
becoming their biggest creditor. Exactly. Which

00:17:57.819 --> 00:18:01.059
gave him control. When Kmart emerged from bankruptcy,

00:18:01.359 --> 00:18:04.309
he became the new chairman. And Lampert had a

00:18:04.309 --> 00:18:07.109
very, very specific philosophy. He was a hedge

00:18:07.109 --> 00:18:10.109
fund guy, not a merchant. He didn't grow up stocking

00:18:10.109 --> 00:18:12.250
shells like Sam Walton or Harry Cunningham. He's

00:18:12.250 --> 00:18:15.289
a numbers guy. A pure numbers guy. His view was,

00:18:15.470 --> 00:18:18.630
and this is a direct quote, sales without profit

00:18:18.630 --> 00:18:21.210
do not allow a business to be successful. Which,

00:18:21.250 --> 00:18:23.289
I mean, that sounds perfectly logical on paper.

00:18:23.349 --> 00:18:25.069
You don't want to lose money on sales. It does

00:18:25.069 --> 00:18:27.950
sound logical. But in the world of retail, sometimes

00:18:27.950 --> 00:18:30.960
you need to spend money to make money. You have

00:18:30.960 --> 00:18:33.200
to renovate stores. You have to run big ad campaigns.

00:18:33.460 --> 00:18:35.720
You have to drive traffic, even if the margins

00:18:35.720 --> 00:18:38.500
on some items are thin, because that traffic

00:18:38.500 --> 00:18:42.240
buys other, more profitable things. Lampert prioritized

00:18:42.240 --> 00:18:44.519
the balance sheet above all else. He cut costs.

00:18:45.119 --> 00:18:47.720
Ruthlessly. He didn't want to spend a dime on

00:18:47.720 --> 00:18:49.920
renovating stores if the ROI wasn't guaranteed

00:18:49.920 --> 00:18:53.119
almost immediately. Many analysts at the time

00:18:53.119 --> 00:18:55.180
and since would argue that he was stripping the

00:18:55.180 --> 00:18:57.279
assets. He was treating the company more like

00:18:57.279 --> 00:18:59.500
a real estate portfolio than an actual living,

00:18:59.599 --> 00:19:02.220
breathing retailer. That's the argument. And

00:19:02.220 --> 00:19:05.119
then he made the move that just shocked the entire

00:19:05.119 --> 00:19:10.039
financial world. The Sears merger. In 2004, Kmart,

00:19:10.259 --> 00:19:12.579
this company that had just clawed its way out

00:19:12.579 --> 00:19:15.279
of a massive bankruptcy, announced it was purchasing

00:19:15.279 --> 00:19:19.589
Sears. For $11 billion. So let me get this straight.

00:19:19.670 --> 00:19:23.369
A struggling, just out of bankruptcy Kmart buys

00:19:23.369 --> 00:19:27.609
a struggling, slowly dying Sears. That's exactly

00:19:27.609 --> 00:19:29.869
what happened. They call the new parent company

00:19:29.869 --> 00:19:32.920
Sears Holdings Corporation. The idea supposedly

00:19:32.920 --> 00:19:36.240
was to create this new hybrid retailer. They

00:19:36.240 --> 00:19:37.720
thought they could cross -sell. They started

00:19:37.720 --> 00:19:40.220
putting Sears' famous house brands like Kenmore

00:19:40.220 --> 00:19:42.880
Appliances and Craftsman Tools into Kmart stores.

00:19:43.119 --> 00:19:44.920
Oh, I remember seeing that. It was so weird.

00:19:44.980 --> 00:19:46.720
You'd walk into a Kmart and there'd be this whole

00:19:46.720 --> 00:19:48.779
wall of Craftsman lawnmowers right next to the

00:19:48.779 --> 00:19:51.380
pantry section. It felt disjointed. It was a

00:19:51.380 --> 00:19:53.400
very strange mix. But the reality was they just

00:19:53.400 --> 00:19:55.339
merged two companies that both had the exact

00:19:55.339 --> 00:19:57.779
same massive unsolved problems. Problems with

00:19:57.779 --> 00:19:59.640
inventory, problems with the store experience,

00:19:59.920 --> 00:20:01.990
and problems with brand. relevance in the 21st

00:20:01.990 --> 00:20:04.369
century. And neither one had ever solved that

00:20:04.369 --> 00:20:07.130
tech gap with Walmart and Target. Not even close.

00:20:07.390 --> 00:20:10.390
So now you didn't have two sinking ships. You

00:20:10.390 --> 00:20:13.049
just had one much bigger, much more complicated

00:20:13.049 --> 00:20:15.250
sinking ship. And the decline from that point

00:20:15.250 --> 00:20:18.269
on, which it wasn't a sudden crash. It was just

00:20:18.269 --> 00:20:21.390
a slow, painful bleed. The slow bleed is the

00:20:21.390 --> 00:20:23.670
perfect way to describe the period from, say,

00:20:23.789 --> 00:20:27.630
2010 to 2018. It wasn't a sudden event. It was

00:20:27.630 --> 00:20:31.250
a long, agonizing decay. Reports just kept coming

00:20:31.250 --> 00:20:33.089
out about the terrible condition of the stores.

00:20:33.230 --> 00:20:35.569
Oh, yeah. Ceiling tiles falling down, dirty floors,

00:20:35.750 --> 00:20:38.549
disorganized shelves, roofs leaking. It became

00:20:38.549 --> 00:20:41.890
a meme almost. The sad Kmart aesthetic became

00:20:41.890 --> 00:20:44.470
a whole thing online. It did. There are whole

00:20:44.470 --> 00:20:46.990
Internet communities dedicated to just photographing

00:20:46.990 --> 00:20:49.109
the decay of these stores. Right. And then came

00:20:49.109 --> 00:20:50.990
the data breaches, which made things even worse.

00:20:51.309 --> 00:20:53.609
2014, there was malware in their payment systems.

00:20:53.849 --> 00:20:56.869
Then in 2017, credit card information was exposed.

00:20:57.230 --> 00:21:00.150
It just completely eroded any trust that was

00:21:00.150 --> 00:21:02.390
left in the brand. And all the while, Lampert

00:21:02.390 --> 00:21:04.609
just kept closing stores. It was liquidation

00:21:04.609 --> 00:21:07.089
by attrition. Just round after round of closures.

00:21:07.170 --> 00:21:11.089
2011, 2014, 2016, 2017. Every few months, you'd

00:21:11.089 --> 00:21:12.890
see a new list of 100 stores that were closing.

00:21:13.289 --> 00:21:15.450
And I remember reading something just incredible

00:21:15.450 --> 00:21:18.750
about their advertising strategy, or lack thereof,

00:21:18.910 --> 00:21:21.950
in 2017. Yes. This is one of the most telling

00:21:21.950 --> 00:21:25.410
details. In the 2017 holiday season, the biggest,

00:21:25.490 --> 00:21:27.710
most important shopping time of the year, the

00:21:27.710 --> 00:21:30.250
time when every single retailer is screaming

00:21:30.250 --> 00:21:34.130
for your attention, Kmart ran exactly zero television

00:21:34.130 --> 00:21:37.589
ads. Zero. None. Not a single one. That just

00:21:37.589 --> 00:21:39.289
feels like giving up. That feels like waving

00:21:39.289 --> 00:21:42.130
the white flag. They claimed it was a pivot to

00:21:42.130 --> 00:21:44.299
digital marketing. But to the average consumer,

00:21:44.599 --> 00:21:46.539
it just looked like the brand had completely

00:21:46.539 --> 00:21:50.319
ceased to exist. In 2018, the last Super Kmart

00:21:50.319 --> 00:21:53.420
closed in Warren, Ohio. The whole grocery store

00:21:53.420 --> 00:21:55.799
concept was officially dead. Which brings us,

00:21:55.859 --> 00:21:58.279
inevitably, to the second bankruptcy. October

00:21:58.279 --> 00:22:01.859
2018. Sears Holdings files for Chapter 11. The

00:22:01.859 --> 00:22:03.980
Great Lampert experiment had officially failed

00:22:03.980 --> 00:22:06.220
to turn the retailer around. But even then, Kmart

00:22:06.220 --> 00:22:08.180
didn't disappear completely. Not right away.

00:22:08.420 --> 00:22:11.220
No. In a controversial move, Lampert created

00:22:11.220 --> 00:22:14.079
a new entity called TransformCo and basically

00:22:14.079 --> 00:22:15.980
bought the remaining assets out of bankruptcy

00:22:15.980 --> 00:22:18.920
himself to prevent a total liquidation. So he

00:22:18.920 --> 00:22:21.819
sold the company to himself. Essentially. But

00:22:21.819 --> 00:22:24.779
from 2019 onward, it was just an extinction event

00:22:24.779 --> 00:22:27.710
in slow motion. We can literally track the timeline

00:22:27.710 --> 00:22:30.390
of extinction by the key milestones. Walk us

00:22:30.390 --> 00:22:31.970
through that timeline. It really is like watching

00:22:31.970 --> 00:22:34.769
a species just go extinct. Okay, so 2019 saw

00:22:34.769 --> 00:22:37.569
another massive wave of closures. That's the

00:22:37.569 --> 00:22:39.250
year they pulled out of states like Arkansas,

00:22:39.609 --> 00:22:43.509
Georgia, and Kansas entirely. The map was getting

00:22:43.509 --> 00:22:46.569
emptier and emptier. Then 2021 was a big one,

00:22:46.630 --> 00:22:49.009
wasn't it? A really symbolic blow. It was a gut

00:22:49.009 --> 00:22:52.769
punch. In 2021, Kmart closed its last remaining

00:22:52.769 --> 00:22:55.170
store in the state of Michigan. In Marshall,

00:22:55.269 --> 00:22:56.809
Michigan. The home state, the state where it

00:22:56.809 --> 00:22:59.410
all began. The birthplace. Closing the last store

00:22:59.410 --> 00:23:01.690
in the state where S .S. Krigich started it all

00:23:01.690 --> 00:23:04.569
over a century before. That same year, they closed

00:23:04.569 --> 00:23:06.890
their last West Coast store in Grass Valley,

00:23:07.029 --> 00:23:09.849
California. The entire western half of the country

00:23:09.849 --> 00:23:13.049
was now a Kmart -free zone. And by 2022, it was

00:23:13.049 --> 00:23:15.309
down to just a handful. Just four stores left

00:23:15.309 --> 00:23:17.910
in the mainland U .S., three in New Jersey, and

00:23:17.910 --> 00:23:20.029
the one in Florida. Why did New Jersey hold out

00:23:20.029 --> 00:23:22.210
for so long? Any idea? That's a good question.

00:23:22.970 --> 00:23:25.809
Probably a mix of factors. High population density,

00:23:26.009 --> 00:23:28.450
maybe some older demographics who were loyal

00:23:28.450 --> 00:23:31.730
shoppers, favorable long -term leases. But even

00:23:31.730 --> 00:23:34.190
they couldn't hold on forever. Westwood, New

00:23:34.190 --> 00:23:36.970
Jersey closed in 2023. And then there was the

00:23:36.970 --> 00:23:39.329
Bridgehampton, New York store. That one was a

00:23:39.329 --> 00:23:41.490
fascinating case study. It really was. It was

00:23:41.490 --> 00:23:44.029
one of the last to go, closing on October 20.

00:23:44.549 --> 00:23:47.670
2024. Why did that particular one survive for

00:23:47.670 --> 00:23:49.849
so long? I mean, Bridge Hampton is in the Hamptons.

00:23:49.869 --> 00:23:52.089
It's an extremely wealthy area. And that's exactly

00:23:52.089 --> 00:23:53.730
why it survived. It was all about isolation.

00:23:54.109 --> 00:23:57.390
The nearest Walmart or Target was a 45 -minute

00:23:57.390 --> 00:23:59.690
drive away, sometimes longer with Hamptons traffic.

00:23:59.930 --> 00:24:02.069
So it had a captive market. A completely captive

00:24:02.069 --> 00:24:04.930
market. The locals, even the very wealthy ones,

00:24:05.109 --> 00:24:07.630
still needed a place to buy basic household goods,

00:24:08.210 --> 00:24:10.549
toilet paper, cleaning supplies, light bulbs,

00:24:10.670 --> 00:24:12.769
without having to drive for an hour and a half

00:24:12.769 --> 00:24:15.779
round trip. But even that perfect isolated environment

00:24:15.779 --> 00:24:18.380
wasn't enough to save it in the end. And as the

00:24:18.380 --> 00:24:20.819
mainland stores vanished, the islands started

00:24:20.819 --> 00:24:23.460
to fall too. Right. The U .S. Virgin Islands,

00:24:23.619 --> 00:24:25.400
which had been a stronghold for a long time,

00:24:25.500 --> 00:24:28.839
the store in Sunny Isle on St. Croix closed on

00:24:28.839 --> 00:24:32.940
July 5, 2025. Then the Lockhart Gardens store

00:24:32.940 --> 00:24:36.019
on St. Thomas closed just a month later on August

00:24:36.019 --> 00:24:39.839
16, 2025. So that brings us right back to today,

00:24:40.039 --> 00:24:43.390
Valentine's Day 2026. Let's talk about what's

00:24:43.390 --> 00:24:45.730
actually left. Let's talk about that mainland

00:24:45.730 --> 00:24:48.930
anomaly down in Miami. This is truly the strangest,

00:24:48.930 --> 00:24:51.769
most surreal part of the entire story. The last

00:24:51.769 --> 00:24:54.730
Kmart in the mainland United States is in Miami,

00:24:54.910 --> 00:24:57.869
Florida, in an area called Kendale Lakes. But

00:24:57.869 --> 00:25:00.029
if you go there expecting to see a Kmart, you're

00:25:00.029 --> 00:25:02.410
going to be very, very confused. Why? What is

00:25:02.410 --> 00:25:04.819
it? Because it's not really a Kmart. The main

00:25:04.819 --> 00:25:07.240
store space, the big 80 ,000 square foot box,

00:25:07.359 --> 00:25:09.720
was leased out a few years ago to a home decor

00:25:09.720 --> 00:25:12.680
chain called At Home. Okay, so where is the Kmart?

00:25:12.819 --> 00:25:14.599
The Kmart now operates out of what used to be

00:25:14.599 --> 00:25:16.380
the building's garden center. Wait, what? So

00:25:16.380 --> 00:25:18.140
it's a tiny little store that's bolted onto the

00:25:18.140 --> 00:25:20.619
side of another store? Exactly. It's about the

00:25:20.619 --> 00:25:23.619
size of a CVS or a Walgreens. They sell a very

00:25:23.619 --> 00:25:25.920
limited selection of pantry items, a few small

00:25:25.920 --> 00:25:29.079
appliances, some cleaning supplies. It's a ghost

00:25:29.079 --> 00:25:31.660
of a store. It's a placeholder. Why does it even

00:25:31.660 --> 00:25:35.259
exist? Nobody knows for sure. It likely exists

00:25:35.259 --> 00:25:37.400
just to satisfy some weird clause in a lease

00:25:37.400 --> 00:25:39.579
agreement or maybe to hold on to the trademark

00:25:39.579 --> 00:25:43.920
in the U .S. But it is Kmart in name only. It's

00:25:43.920 --> 00:25:47.240
not a department store. That is profoundly sad

00:25:47.240 --> 00:25:49.910
in a way. It is. But if you want to see a Kmart

00:25:49.910 --> 00:25:52.809
that is still in its full glory, a thriving Kmart,

00:25:52.970 --> 00:25:55.730
you have to get on a plane and go to Guam. Guam.

00:25:55.730 --> 00:25:57.809
You called it the retail Galapagos. That is the

00:25:57.809 --> 00:26:00.289
perfect term for it. Because the Kmart in Temening,

00:26:00.470 --> 00:26:03.269
Guam, is an absolute beast. It opened in 1995,

00:26:03.529 --> 00:26:06.130
and it is 170 ,000 square feet. It's one of the

00:26:06.130 --> 00:26:07.890
largest Kmarts ever built. And it's still open.

00:26:07.970 --> 00:26:11.369
Still doing well. As of 2026, yes. And for many,

00:26:11.430 --> 00:26:13.349
many years, it was the single highest -grossing

00:26:13.349 --> 00:26:15.819
Kmart in the entire world. We're talking sales

00:26:15.819 --> 00:26:18.559
of around $100 million a year from one store.

00:26:18.900 --> 00:26:21.980
Wow. Okay, so why Grom? What's the magic formula?

00:26:22.000 --> 00:26:23.700
Why does it work there when it failed everywhere

00:26:23.700 --> 00:26:26.559
else? Isolation. The same reason the Bridgehampton

00:26:26.559 --> 00:26:28.759
store lasted so long, but on a much bigger scale.

00:26:29.240 --> 00:26:32.869
Think about it. Amazon shipping to Guam. is incredibly

00:26:32.869 --> 00:26:36.390
slow and expensive there is no nearby target

00:26:36.390 --> 00:26:39.509
or walmart supercenter to undercut them on price

00:26:39.509 --> 00:26:42.450
so it's the only game in town for a lot of things

00:26:42.450 --> 00:26:45.690
yes it serves as the pantry for the entire island

00:26:45.690 --> 00:26:48.710
but then there's a second really strange reason

00:26:48.710 --> 00:26:52.220
for its success tourism Tourists? Who goes to

00:26:52.220 --> 00:26:54.900
Kmart as a tourist? Asian tourists, specifically.

00:26:55.339 --> 00:26:57.460
Tourists from Japan and South Korea, they visit

00:26:57.460 --> 00:26:59.799
Guam, and they make a special trip to Kmart to

00:26:59.799 --> 00:27:02.240
buy American snacks, cases of spam, chocolates,

00:27:02.460 --> 00:27:04.339
things they can't get at home. For them, it's

00:27:04.339 --> 00:27:06.119
a slice of Americana. It's a tourist destination.

00:27:06.420 --> 00:27:08.519
It blows my mind. It's a totally unique retail

00:27:08.519 --> 00:27:11.240
ecosystem where the modern predators, Amazon

00:27:11.240 --> 00:27:13.440
and Walmart, they just can't reach it effectively.

00:27:13.880 --> 00:27:15.579
And you said there's still one left in the U

00:27:15.579 --> 00:27:18.359
.S. Virgin Islands, too. Yes. As of the 2025

00:27:18.359 --> 00:27:21.240
closures, the location at the Tutu Park Mall

00:27:21.240 --> 00:27:23.599
in St. Thomas is the last holdout in the Virgin

00:27:23.599 --> 00:27:26.559
Islands. So the entire Kmart empire has been

00:27:26.559 --> 00:27:29.240
reduced to a garden center in Miami and a few

00:27:29.240 --> 00:27:31.980
heavily fortified island fortresses. That is

00:27:31.980 --> 00:27:35.160
an incredible story. OK, before we wrap this

00:27:35.160 --> 00:27:37.259
up, I want to hit part seven, the fascinating

00:27:37.259 --> 00:27:39.359
footnotes, because in your research, you found

00:27:39.359 --> 00:27:42.829
some really, really weird stuff. that kmart tried

00:27:42.829 --> 00:27:44.730
over the years well they tried everything they

00:27:44.730 --> 00:27:47.410
were desperate to innovate but often in the strangest

00:27:47.410 --> 00:27:50.049
possible ways for instance did you know about

00:27:50.049 --> 00:27:53.450
kmart chef kmart chef was that like a line of

00:27:53.450 --> 00:27:56.809
cookware no it was a restaurant chain from 1967

00:27:56.809 --> 00:28:00.690
to 1974 they ran a fast food chain in the parking

00:28:00.690 --> 00:28:03.670
lots of kmart stores called kmart chef they served

00:28:03.670 --> 00:28:07.410
hamburgers fries Hot dogs. It was their attempt

00:28:07.410 --> 00:28:09.930
to be McDonald's. I had absolutely no idea. I

00:28:09.930 --> 00:28:11.549
can't imagine telling someone, hey, let's go

00:28:11.549 --> 00:28:13.710
out for a nice dinner at Kmart. And it gets weirder.

00:28:13.769 --> 00:28:16.190
Then there was Kmart Dental. Stop it. You're

00:28:16.190 --> 00:28:18.230
making that up. I am not. It was a prototype.

00:28:18.369 --> 00:28:21.170
A dentist's office located inside a Miami Kmart

00:28:21.170 --> 00:28:23.369
store. You could get your teeth cleaned and then

00:28:23.369 --> 00:28:25.690
go buy a lawnmower in the same trip. That sounds

00:28:25.690 --> 00:28:28.250
both terrifying and somehow convenient. Clean

00:28:28.250 --> 00:28:30.029
up on aisle four and we have a root canal on

00:28:30.029 --> 00:28:32.769
aisle five. And let's not forget blue light internet.

00:28:33.089 --> 00:28:35.269
Oh, wait. I actually vaguely remember this one.

00:28:35.309 --> 00:28:38.009
The blue CD -ROMs. That's the one. Launched in

00:28:38.009 --> 00:28:41.710
1999. It was a dial -up internet service to compete

00:28:41.710 --> 00:28:44.450
directly with AOL. They gave away free internet

00:28:44.450 --> 00:28:47.630
access, or very cheap access, to try and get

00:28:47.630 --> 00:28:49.670
people to shop on their website. And it actually

00:28:49.670 --> 00:28:51.599
worked for a little while, didn't it? It was

00:28:51.599 --> 00:28:54.759
surprisingly popular for a brief moment right

00:28:54.759 --> 00:28:57.920
before the dot -com bottle burst. It showed that

00:28:57.920 --> 00:28:59.519
they understood the internet was coming. They

00:28:59.519 --> 00:29:02.359
just had absolutely no idea how to properly monetize

00:29:02.359 --> 00:29:04.900
it or integrate it with their stores. It just

00:29:04.900 --> 00:29:06.480
shows how much stuff they were throwing at the

00:29:06.480 --> 00:29:08.740
wall, hoping something would stick. And, you

00:29:08.740 --> 00:29:10.420
know, we should also mention their environmental

00:29:10.420 --> 00:29:13.720
record, which... Wasn't great. They got hit with

00:29:13.720 --> 00:29:17.720
some heavy EPA fines in 2007 for mishandling

00:29:17.720 --> 00:29:19.880
hazardous waste. And there was a big scandal

00:29:19.880 --> 00:29:22.940
in 2012, an investigation by Mercy for animals

00:29:22.940 --> 00:29:25.640
regarding their pork suppliers and the use of

00:29:25.640 --> 00:29:27.640
gestation crates. Did they do anything about

00:29:27.640 --> 00:29:30.160
that? They did. To their credit, they pledged

00:29:30.160 --> 00:29:31.839
to phase them out after the report came out.

00:29:31.940 --> 00:29:33.819
But on the other side of that coin, they were

00:29:33.819 --> 00:29:37.000
also huge philanthropists, right? Massive. We

00:29:37.000 --> 00:29:39.420
can't overlook that part of their legacy. For

00:29:39.420 --> 00:29:41.720
a very long time, they were the number one corporate

00:29:41.720 --> 00:29:45.220
sponsor for the March of Dimes. They raised $114

00:29:45.220 --> 00:29:49.400
million over 30 years. And they raised over $59

00:29:49.400 --> 00:29:52.099
million for St. Jude's Children's Research Hospital.

00:29:52.359 --> 00:29:54.960
They were a major part of the community fabric

00:29:54.960 --> 00:29:57.119
in thousands of towns across America. And they

00:29:57.119 --> 00:29:59.740
went racing. They did. If you watched IndyCar

00:29:59.740 --> 00:30:02.319
or NASCAR in the 90s, the Kmart car was iconic,

00:30:02.619 --> 00:30:05.299
sponsoring Newman Haas Racing. Michael Andretti

00:30:05.299 --> 00:30:07.299
won a championship in a Kmart -sponsored car

00:30:07.299 --> 00:30:10.440
in 1991. They sponsored Daryl Waltrip in NASCAR.

00:30:10.559 --> 00:30:13.839
That red K was everywhere. So here we are, February

00:30:13.839 --> 00:30:17.960
14, 2026. The autopsy is complete. When you put

00:30:17.960 --> 00:30:19.420
it all together, what does this all mean? What's

00:30:19.420 --> 00:30:21.460
the lesson here? If you look at that whole trajectory

00:30:21.460 --> 00:30:25.720
from a $6 ,700 investment by SS Kredge to a global

00:30:25.720 --> 00:30:29.420
retail powerhouse to this cautionary tale, I

00:30:29.420 --> 00:30:31.539
think the lesson is painfully clear. No retailer

00:30:31.539 --> 00:30:34.359
is too big to fail. It's the Titan problem. You

00:30:34.359 --> 00:30:36.240
get so big, you become arrogant and you think

00:30:36.240 --> 00:30:39.359
you can't fall. Exactly. And the failure to digitize

00:30:39.359 --> 00:30:42.140
their supply chains in the 90s. that sealed their

00:30:42.140 --> 00:30:44.819
fate. By the time Amazon became a dominant force,

00:30:45.039 --> 00:30:47.460
Kmart was already dead. It just didn't know it

00:30:47.460 --> 00:30:50.160
yet. They lost the war to Walmart in the 1990s,

00:30:50.160 --> 00:30:53.400
not to Amazon in the 2010s. Stagnation is death,

00:30:53.599 --> 00:30:56.099
especially in retail. Precisely. You have to

00:30:56.099 --> 00:30:58.160
keep moving, you have to keep investing, or you

00:30:58.160 --> 00:31:00.500
become a relic. So here's a final provocative

00:31:00.500 --> 00:31:03.019
thought for you listening. The only places that

00:31:03.019 --> 00:31:06.619
Kmart truly survives today, Guam, the USVI, are

00:31:06.619 --> 00:31:08.859
places where geography itself creates a high

00:31:08.859 --> 00:31:11.140
barrier to entry for their competitors. It's

00:31:11.140 --> 00:31:14.359
all about isolation. So is isolation the only

00:31:14.359 --> 00:31:17.140
protection left for the old way of doing retail?

00:31:17.319 --> 00:31:20.160
Can a physical store only survive if the digital

00:31:20.160 --> 00:31:22.900
giants literally can't reach its customers effectively?

00:31:23.440 --> 00:31:25.599
It's a fascinating question and one worth asking

00:31:25.599 --> 00:31:27.819
as we watch the entire retail landscape continue

00:31:27.819 --> 00:31:30.059
to shift. change around us I want you to go home

00:31:30.059 --> 00:31:32.380
and check your attics check your basements if

00:31:32.380 --> 00:31:34.299
you have any old blue light merchandise or maybe

00:31:34.299 --> 00:31:36.880
a Kmart receipt from 1994 tucked inside a book

00:31:36.880 --> 00:31:39.059
hold on to it it's a relic of a fallen empire

00:31:39.059 --> 00:31:41.420
thanks for listening to this deep dive we'll

00:31:41.420 --> 00:31:42.039
see you next time
