WEBVTT

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Welcome back to the Deep Dive. Today we are taking

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a stack of sources, articles, legal filings,

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financial breakdowns about a single individual.

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Yeah. And we're going to try to answer a question

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that honestly, it just baffles me. What's that?

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How does a man get fired from a corporate job

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at age 32 with no money, forced to borrow 10

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grand from his mother just to pay rent? Right.

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And end up reshaping the entire skyline of New

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York City and owning an NFL franchise? It sounds

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like fiction. I mean, if you pitch this as a

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screenplay, they tell you the second act is just

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too unrealistic. Right. But we are talking about

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Stephen M. Ross. Stephen M. Ross. Yeah. The man,

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the myth, the mega developer. The man behind

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related companies, Hudson Yards, the Miami Dolphins.

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But I want to be real. clear right off the bat.

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This isn't just a biography. We aren't here to

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just list the buildings he bought or his net

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worth. Right. If we just list his assets, we

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completely missed the point. We're here to understand

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the anatomy of a mega developer. The anatomy.

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I like that. We need to look at how tax law,

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real estate, and professional sports ownership

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intersect. Because when you peel back the layers

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on Ross, you realize... These aren't separate

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businesses. No. They are all pieces of one massive

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self -sustaining ecosystem. That's what jumped

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out at me in all the research. He's not just

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a guy who likes football and also happens to

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like skyscrapers. There is a very specific machinery

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underneath it all. It's all about leverage. It's

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about incentives. And it's about understanding

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the rules better than anyone else in the room.

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Specifically. The boring rules. The tax code.

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The tax code. That's the secret. We're going

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to get deep into the weeds on that because I

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think that's the secret sauce here. We have a

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lot to cover. A ton. We've got the origin story

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in Detroit, the aha moment with affordable housing,

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the massive gamble of Hudson Yards. The whole

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Miami Dolphins saga. And of course, the controversies,

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which are significant. Oh, yeah. But let's start

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at the beginning. Because before he was a billionaire,

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he was just a kid in Detroit. Born in 1940. A

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Jewish family in Detroit. He goes to Mumford

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High School. And I think, to understand Ross,

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you really have to look at his education. Okay.

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It's not the typical path for a developer. Not

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at all. I was looking at this timeline. It's

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pretty exhaustive. He starts at the University

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of Florida. Right. Then transfers to the University

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of Michigan, which, you know, becomes this huge

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part of his life later on. Gets a BBA in 1962.

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Standard stuff so far. Then he goes to Wayne

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State for a law degree. But then, and this is

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the part where I really paused, he goes to NYU.

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For a master of laws in taxation and LLM. Taxation.

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Okay, help me out here. Usually when we talk

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about real estate tycoons, we're talking about

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these guys with big personalities, sales guys,

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maybe architects. Guys who can sell a vision.

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Exactly. A master's degree in taxation sounds,

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well, it sounds dry. It is dry. It's incredibly

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dry. But that is the superpower. See, most people

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look at a building and see bricks, glass, maybe

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a nice lobby. They see rental income. Right.

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They see the physical thing. Ross looks at a

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building and sees a depreciation schedule. He

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sees tax credits. He sees a vehicle for sheltering

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income. So he's seeing the matrix code behind

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the building. He's seeing the matrix code. That's

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it. He's looking at the invisible financial structure

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that makes the physical structure possible. And

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that specific degree, that specialized knowledge

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of the tax code is the tool that eventually builds

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the entire empire. But it didn't happen immediately.

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Oh, no. Not even close. Right. Because first,

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he has to fail. And he fails hard. He moves to

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New York, works at Bear Stearns in corporate

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finance. This is the late 60s, early 70s. It's

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a prestigious job. I mean, Bear Stearns, but

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Ross. While all the reports suggest he wasn't

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great at taking orders. Doesn't play well with

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others. He had a certain arrogance or maybe just

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a conviction that he knew better. So in 1972,

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he gets into a big conflict with a superior.

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And it's not just, you know, a slap on the wrist.

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No. He gets fired. I want to just pause on this

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moment because it's so easy to gloss over in

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retrospect. It's 1972. You are 32 years old.

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Yeah. You have a law degree, a master's degree.

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You're in the most competitive city on earth

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and you just got canned. Utterly terrifying.

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That is a terrifying position to be in. It is.

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And he wasn't sitting on some pile of cash. The

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sources all say he literally didn't have the

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liquidity to maintain his lifestyle. He had to

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go to his mother. His mom. And borrow $10 ,000.

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Which, accounting for inflation, is about $67

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,000 today. So it's a keep the lights on loan.

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It's not seed capital for an empire. No, it's

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survival money. It's please don't get evicted

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from my apartment money. And this is the pivot

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point. This is where most people would polish

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the resume, maybe shave the mustache and go interview

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at another bank. Right. Get back on the horse.

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Ross decides he is done answering to people.

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He decides to leverage the one thing he has that

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others don't. The tax degree. That deep technical

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knowledge of tax law. And this brings us to the

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first big chapter of his success, affordable

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housing. But not, he wasn't building it, right?

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He was structuring it. Correct. He wasn't the

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guy with the hard hat. Not yet. I need you to

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explain this to me like I'm five years old. Or

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maybe. Maybe like I'm a dentist in 1972 with

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some extra cash. What exactly was Ross selling?

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Because he wasn't pouring concrete yet. Okay.

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Okay. Let's role play. You're a wealthy dentist

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or a partner at a law firm in 1972. You're making,

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say, $100 ,000 a year, which is a lot of money

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back then. A huge amount. But the top marginal

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tax rate in the 70s was incredibly high. Over

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50 percent, sometimes up to 70 percent. So the

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government is just taking this huge chunk of

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my money. I'm looking for a way to keep it. You're

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desperate to keep it. Exactly. So enter Stephen

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Ross. He comes to you and says, I have an investment

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opportunity in government subsidized affordable

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housing. OK, that doesn't sound very sexy. Affordable

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housing? No, it doesn't sound like a big moneymaker.

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Rents are capped. But Ross explains the tax side

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of it. The federal government wants this housing

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built, so they offer massive incentives. Specifically.

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they allow you to accelerate depreciation. Depreciation.

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Okay, so on paper, the building is losing value.

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On paper, yes. Even if it's appreciating in the

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real world. So Ross structures a deal where you,

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the dentist, put in, say, $10 ,000 cash. Okay,

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I'm in for $10 ,000. But because of how the tax

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laws worked in, that investment allows you to

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claim a loss on your taxes that is much, much

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larger than your actual cash investment. So it's

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a paper loss. It's a paper loss. Let's say you

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can claim a $40 ,000 loss on paper. You take

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that $40 ,000 loss, you apply it against your

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dentist income, and suddenly that $20 ,000 you

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were going to pay to the IRS, it's gone. You

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owe them nothing. Wait, so I give Ross $10 ,000

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and I save $20 ,000 in taxes? Yes. I've just

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made money instantly by signing a piece of paper.

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Precisely. You made a 100 % return on your money

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via the tax code, regardless of whether the building

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ever collects a single dime in rent. Wow. Ross

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wasn't selling apartments. He was selling tax

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shelters. He was syndicating these deals, pooling

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money from all these wealthy investors who needed

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to hide income, and then using that money to

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back the actual affordable housing developers.

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That is, well it's genius. It's completely genius.

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And it explains why that tax degree was so important.

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Everything. A regular developer wouldn't know

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how to structure the partnership to maximize

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those write -offs. No way. He monetized the boring

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stuff. He realized that the government was effectively

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handing out free money to encourage this kind

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of housing. But you needed a translator to access

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it. And he was the translator. He was the Rosetta

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Stone for tax shelters. Yeah. In his first year,

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1972, the same year he was fired and broke, he

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made $150 ,000. That is a massive amount of money

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for 1972. That's top 1 % income, like immediately.

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Immediately. And that is the birth of related

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companies. Which was originally called Related

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Housing Company. Exactly. It was built entirely

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on this specific niche. Subsidized, low to moderate

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income housing. For years, he became one of the

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biggest affordable housing developers in the

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country. It's just fascinating because today

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the brand related means the exact opposite. The

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total opposite. It means $10 million condos,

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Equinox gyms, Hudson Yards luxury. It's the definition

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of elite. How does he bridge that gap? How do

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you go from Section 8 housing to selling penthouses

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to oligarchs? It's two things, capital and confidence.

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The affordable housing business is great because

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it's really low risk. The government guarantees

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the rent. Built in safety net. Right. And it

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generates steady cash flow. So it built his balance

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sheet. By the 1980s, he has enough of his own

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money to start taking bigger and bigger risks.

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And he starts moving into Manhattan. He starts

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moving into Manhattan. He starts hiring star

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architects, you know, famous architects like

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Robert A .M. Stern. He wants his buildings to

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be landmarks. He moves from need to want. That's

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a great way to put it. Affordable housing is

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a need product. Luxury real estate is a want

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product. An aspirational product. Totally. And

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Ross realized that if you wanted to leave a mark

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on the skyline, and make billions instead of

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millions. He had to capture that want market.

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Which leads us to the behemoth. I mean, the portfolio

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today is valued at over $60 billion. It's staggering.

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They are everywhere. London, Abu Dhabi, LA, Chicago.

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But the crown jewel, the thing that I think will

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define his obituary one day, is Hudson Yards.

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The city within a city. I walked through there

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recently. It is just, it's overwhelming. It feels

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like a different planet compared to the rest

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of Hell's Kitchen. It does. But the backstory

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of just building it is insane. It is the largest

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private real estate development in the history

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of the United States. Largest? Ever. 28 acres

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on the west side of Manhattan. But here is the

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kicker. And this is what blows people's minds.

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There was no land there. What do you mean there

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was no land? I've stood on it. What you were

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standing on was man -made. It was an active Long

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Island Railroad train yard. Dozens of tracks

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with trains running 2047. To build Hudson Yards,

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Ross had to build a massive platform over the

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trains. Wait, wait, wait. So the skyscrapers,

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the vessel, the mall, it's all sitting on a giant

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table. Essentially, yes. Yeah. A ridiculously

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complex and expensive table. They had to drill

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these huge support pillars called caissons down

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into the bedrock between the train tracks. While

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the trains were running. While the trains were

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running. Right. Without hitting the trains or

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the high voltage lines. And then they had to

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build a massive concrete and steel deck on top

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of those pillars. And then they could start building

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the hundred story buildings on top of that deck.

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The engineering risk alone is staggering. It's

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mind boggling. And what about the cost? Just

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the platform. Just to create. The fake ground

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cost? Roughly a billion dollars per acre. A billion

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dollars an acre? A billion. Just to get to ground

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zero, before you even lay a single brick for

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a lobby, that sounds like financial suicide.

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Why would anyone ever do that? Because if you

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pull it off, you own an entire neighborhood in

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Manhattan. Think about it. Usually developers

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fight over one lot, one corner. A single building.

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Right. Ross manufactured 28 acres of prime real

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estate out of thin air. But to make it pay off,

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he needed tenants and not just any tenants. He

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needed companies that could pay top tier premium

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rents to cover those astronomical construction

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costs. And this brings us to this placemaking

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concept. I read this story about Coach, the handbag

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company, and I think it perfectly illustrates

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how Ross operates. The Coach story is the textbook

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example of Ross's dealmaking style. It really

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is. He needed an anchor tenant. The first domino.

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Exactly. Without a big name, no one else comes.

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So he wanted Coach to move their global headquarters

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to Hudson Yards. Coach was, you know, skeptical.

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Of course. Why would they move to a noisy construction

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zone over a rail yard? It's far west. It's totally

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unproven. Right. So Ross didn't just offer them

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a good lease. He offered to alter the physical

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reality of the building for them. What does that

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mean? Coach wanted a specific kind of internal

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flow for their creative teams, this very open,

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collaborative feel. So Ross redesigned the tower

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to include a massive multi -story atrium right

00:12:17.419 --> 00:12:19.059
in the middle of the building. In the middle?

00:12:19.240 --> 00:12:22.379
Yes, specifically for them. He carved out what

00:12:22.379 --> 00:12:24.820
would have been tens of thousands of square feet

00:12:24.820 --> 00:12:27.860
of valuable, rentable office space. So he sacrificed

00:12:27.860 --> 00:12:30.679
rent money just to create a vibe for one tenant.

00:12:31.039 --> 00:12:35.220
Yes. He sacrificed rentable space to create a

00:12:35.220 --> 00:12:39.399
wow factor that closed the deal. And once Coach

00:12:39.399 --> 00:12:42.149
signed on the dotted line... The entire narrative

00:12:42.149 --> 00:12:45.629
changed. Suddenly, Hudson Yards wasn't a risky

00:12:45.629 --> 00:12:48.190
rail yard project. It was the new home of American

00:12:48.190 --> 00:12:50.889
luxury fashion. And then everyone else follows.

00:12:51.049 --> 00:12:54.029
Then L 'Oreal came. Then SAP came. Then the private

00:12:54.029 --> 00:12:56.909
equity giant KKR came. It's the domino effect.

00:12:57.129 --> 00:12:58.830
And this is where we see the difference between

00:12:58.830 --> 00:13:01.309
just being a landlord and being a placemaker.

00:13:01.629 --> 00:13:04.210
It's a huge difference. A landlord rents you

00:13:04.210 --> 00:13:06.870
four walls and a floor. A placemaker curates

00:13:06.870 --> 00:13:09.230
an entire environment. Ross didn't just build

00:13:09.230 --> 00:13:12.570
offices. He built The Shed, a world -class cultural

00:13:12.570 --> 00:13:15.490
center. He built The Vessel, that giant honeycomb

00:13:15.490 --> 00:13:17.669
staircase sculpture that everyone takes pictures

00:13:17.669 --> 00:13:19.610
of. He put in restaurants from Thomas Keller

00:13:19.610 --> 00:13:22.070
and Jose Andres, high -end destination dining.

00:13:22.210 --> 00:13:24.590
And he put in Equinox. Right. And this is crucial.

00:13:24.809 --> 00:13:27.389
This is the ecosystem part. Related Companies

00:13:27.389 --> 00:13:30.330
is a major investor in Equinox Fitness and SoulCycle.

00:13:30.559 --> 00:13:32.519
So he builds the condo you live in. He builds

00:13:32.519 --> 00:13:35.019
the office you work in. And he owns the gym where

00:13:35.019 --> 00:13:37.200
you work out downstairs. And the restaurant where

00:13:37.200 --> 00:13:40.700
you have dinner. He captures every single slice

00:13:40.700 --> 00:13:44.240
of your day. It's the vertical integration of

00:13:44.240 --> 00:13:46.200
the human lifestyle. It's almost like living

00:13:46.200 --> 00:13:48.299
on a cruise ship that never leaves the dock.

00:13:48.480 --> 00:13:51.159
You never have to leave the Stephen Ross ecosystem.

00:13:51.519 --> 00:13:53.240
That is the goal. You control the environment.

00:13:53.340 --> 00:13:55.559
You control the spend. Now, speaking of control.

00:13:56.169 --> 00:13:57.789
We have to pivot. We have to go to the other

00:13:57.789 --> 00:14:00.769
massive pillar of his life. Okay. We've covered

00:14:00.769 --> 00:14:03.409
the tax attorney and the builder. Now we have

00:14:03.409 --> 00:14:06.830
to talk about the sports tycoon. The Miami Dolphins.

00:14:06.850 --> 00:14:08.509
This feels like a totally different world, but

00:14:08.509 --> 00:14:10.690
you argued earlier that it's the same muscle

00:14:10.690 --> 00:14:13.470
group. How does that work? It's all about asset

00:14:13.470 --> 00:14:17.789
appreciation and leverage. So Russ buys 95 %

00:14:17.789 --> 00:14:20.450
of the Dolphins in the stadium for about $1 .1

00:14:20.450 --> 00:14:24.399
billion around 2008, 2009. Okay. And people thought,

00:14:24.559 --> 00:14:27.580
OK, another rich guy buys a toy. But Ross didn't

00:14:27.580 --> 00:14:30.100
treat it like a toy. He treated it like a distressed

00:14:30.100 --> 00:14:32.100
real estate asset. And the stadium was aging,

00:14:32.220 --> 00:14:35.320
right? It wasn't a great venue. It was a concrete

00:14:35.320 --> 00:14:37.720
bowl. It had been beaten up by the Florida sun.

00:14:37.899 --> 00:14:39.960
It wasn't generating the kind of revenue it could.

00:14:40.600 --> 00:14:43.320
Now, usually, this is the part of the story where

00:14:43.320 --> 00:14:45.559
the billionaire owner goes to the city council.

00:14:45.799 --> 00:14:48.019
With his handout. With his handout. It says,

00:14:48.409 --> 00:14:51.669
Build me a brand new shiny stadium. Or I'm moving

00:14:51.669 --> 00:14:54.909
the team to Los Angeles or San Antonio or wherever.

00:14:55.169 --> 00:14:56.929
We see it constantly. It's happening in Buffalo,

00:14:57.210 --> 00:14:59.850
Tennessee, Vegas. It's the standard playbook.

00:15:00.009 --> 00:15:02.450
It is the playbook. And Ross tried it. In 2013,

00:15:02.649 --> 00:15:04.929
he went to the state of Florida and asked for

00:15:04.929 --> 00:15:08.169
public money. About $3 million a year for 30

00:15:08.169 --> 00:15:09.870
years for renovations. Yeah, and they said no.

00:15:10.070 --> 00:15:13.200
The Florida legislature shut him down. Flatly.

00:15:13.259 --> 00:15:14.960
So typically, this is where the owner throws

00:15:14.960 --> 00:15:17.379
a tantrum. Fine, I'm taking my team and leaving.

00:15:17.639 --> 00:15:19.740
Ross didn't. He did something that absolutely

00:15:19.740 --> 00:15:22.159
shocked the NFL community. What did he do? He

00:15:22.159 --> 00:15:24.320
reached into his own pocket and spent roughly

00:15:24.320 --> 00:15:28.360
$500 million of his own money to completely renovate

00:15:28.360 --> 00:15:31.279
Hard Rock Stadium. Half a billion dollars. Now,

00:15:31.320 --> 00:15:33.519
I have to be skeptical here. Why? Is he just

00:15:33.519 --> 00:15:36.360
a benevolent fan who loves the city of Miami?

00:15:37.029 --> 00:15:40.909
Or is there a cold, hard, calculated reason to

00:15:40.909 --> 00:15:44.009
spend $500 million of your own cash? Oh, it's

00:15:44.009 --> 00:15:46.529
absolutely calculated, 100%. Think about it.

00:15:46.570 --> 00:15:49.049
If you take public money, you have public strings

00:15:49.049 --> 00:15:51.889
attached. The city wants a cut of the parking

00:15:51.889 --> 00:15:54.809
revenue. The county wants a say in what events

00:15:54.809 --> 00:15:57.309
you host. The state wants to know why you're

00:15:57.309 --> 00:15:59.669
charging so much for a beer. But if you pay for

00:15:59.669 --> 00:16:01.850
it yourself. You own the revenue streams, all

00:16:01.850 --> 00:16:04.960
of them. And Ross had a vision that went... way,

00:16:04.960 --> 00:16:07.980
way beyond just football. He looked at that stadium

00:16:07.980 --> 00:16:11.519
and realized that an NFL stadium sits empty 350

00:16:11.519 --> 00:16:14.259
days a year. It's a terribly wasted asset. It's

00:16:14.259 --> 00:16:16.799
a terrible use of real estate. Exactly. So he

00:16:16.799 --> 00:16:18.960
renovated the stadium to make it a global entertainment

00:16:18.960 --> 00:16:21.259
hub. He put a roof over the seats. He upgraded

00:16:21.259 --> 00:16:23.220
all the suites. And he brought in tennis. He

00:16:23.220 --> 00:16:24.679
brought in the Miami Open tennis tournament.

00:16:24.840 --> 00:16:27.500
He poached it from its longtime home in Key Biscayne.

00:16:27.679 --> 00:16:30.379
He built a permanent world -class tennis complex

00:16:30.379 --> 00:16:32.899
on the grounds of the football stadium. And then...

00:16:33.279 --> 00:16:35.639
The big one. Formula One. The Miami Grand Prix.

00:16:35.779 --> 00:16:38.240
This is a masterclass in logistics and, frankly,

00:16:38.320 --> 00:16:41.299
in lobbying. He managed to secure a 10 -year

00:16:41.299 --> 00:16:44.740
exclusive contract with F1. Which is a huge deal.

00:16:44.919 --> 00:16:47.799
Huge. But the problem was, where do you race?

00:16:47.960 --> 00:16:49.980
He couldn't shut down downtown Miami like they

00:16:49.980 --> 00:16:52.740
do in Monaco or Singapore. The local opposition

00:16:52.740 --> 00:16:55.019
was just too strong. So he looked at his own

00:16:55.019 --> 00:16:57.360
parking lot. He looked at the vast expanse of

00:16:57.360 --> 00:16:59.960
land surrounding Hard Rock Stadium. And critics

00:16:59.960 --> 00:17:01.659
laughed at first. They said, you're going to

00:17:01.659 --> 00:17:03.899
race these incredible F1 cars in a parking lot.

00:17:03.980 --> 00:17:07.619
Right. But Ross saw a campus. He built a temporary,

00:17:07.859 --> 00:17:10.160
purpose -built circuit. They call it the Miami

00:17:10.160 --> 00:17:13.039
International Autodrome. that winds all around

00:17:13.039 --> 00:17:15.099
the stadium. I looked into the engineering of

00:17:15.099 --> 00:17:17.279
this. It's not just painting lines on asphalt.

00:17:17.500 --> 00:17:20.420
No. F1 cars create immense G -forces and suction.

00:17:20.720 --> 00:17:23.319
They had to lay specialized, high -grade racing

00:17:23.319 --> 00:17:25.960
asphalt on top of the existing grounds, ensure

00:17:25.960 --> 00:17:28.759
drainage, build FIA -certified safety barriers.

00:17:29.059 --> 00:17:30.779
And then a few weeks later, turn it all back

00:17:30.779 --> 00:17:33.400
into a parking lot for football season. A logistical

00:17:33.400 --> 00:17:37.339
nightmare. A nightmare. But it worked. The event

00:17:37.339 --> 00:17:41.809
is a massive cash cow. VIP tickets cost Thousands

00:17:41.809 --> 00:17:45.089
and thousands of dollars. And because Ross owns

00:17:45.089 --> 00:17:47.849
the stadium and the land and paid for the upgrades

00:17:47.849 --> 00:17:50.130
himself. He captures all of that revenue. He

00:17:50.130 --> 00:17:52.690
captures the lion's share. He turned a football

00:17:52.690 --> 00:17:55.509
field into a 365 -day entertainment district

00:17:55.509 --> 00:17:58.369
that hosts a Super Bowl, a college football championship,

00:17:58.769 --> 00:18:02.069
a tennis major, and a Formula One race. It connects

00:18:02.069 --> 00:18:04.349
right back to Hudson Yards. It's placemaking

00:18:04.349 --> 00:18:06.829
again. He's not selling a race. He's selling

00:18:06.829 --> 00:18:09.390
the Miami Grand Prix experience. With the yachts

00:18:09.390 --> 00:18:11.109
and the fake marina and the celebrity clubs,

00:18:11.210 --> 00:18:13.710
yes. He sells the sizzle, and the state comes

00:18:13.710 --> 00:18:15.990
along for the ride. That's his old model. But

00:18:15.990 --> 00:18:18.210
he's also a bit of a maverick within that exclusive

00:18:18.210 --> 00:18:20.569
NFL owners circle, right? He doesn't always just

00:18:20.569 --> 00:18:23.269
vote with a pack. No, he really doesn't. The

00:18:23.269 --> 00:18:25.170
best example of this is the Raiders vote back

00:18:25.170 --> 00:18:29.529
in 2017. OK. The NFL owners voted 31 to 1 to

00:18:29.529 --> 00:18:31.609
approve the Oakland Raiders moving to Las Vegas.

00:18:31.730 --> 00:18:33.829
And Ross was the one. He was the lone dissenter.

00:18:33.950 --> 00:18:37.569
The only no vote. Why? I mean, Las Vegas is a

00:18:37.569 --> 00:18:40.430
goldmine. Why would a guy who loves money so

00:18:40.430 --> 00:18:44.980
much vote against moving a team to Vegas? His

00:18:44.980 --> 00:18:47.299
public reasoning was that he believed the owners

00:18:47.299 --> 00:18:49.200
hadn't done enough to try to keep the team in

00:18:49.200 --> 00:18:51.940
Oakland. He felt that there was a social contract

00:18:51.940 --> 00:18:54.900
with the fan base. Interesting. He thought that

00:18:54.900 --> 00:18:56.799
moving teams too frequently, and you have to

00:18:56.799 --> 00:18:58.720
remember the Rams and Chargers had just moved

00:18:58.720 --> 00:19:01.859
to L .A., eroded the long -term value of the

00:19:01.859 --> 00:19:04.700
NFL brand itself. He was worried about fan loyalty.

00:19:05.000 --> 00:19:07.599
He basically said, if we treat these teams like

00:19:07.599 --> 00:19:09.579
interchangeable widgets that we can just move

00:19:09.579 --> 00:19:12.059
around a chessboard, eventually the fans will

00:19:12.059 --> 00:19:15.549
stop caring. That's surprisingly principled,

00:19:15.549 --> 00:19:17.630
or at least it's a very long -term view versus

00:19:17.630 --> 00:19:20.430
a short -term cash grab. It is. He also threw

00:19:20.430 --> 00:19:22.789
some not -so -subtle shade at the Chargers' ownership,

00:19:23.089 --> 00:19:24.789
suggesting they didn't really try hard enough

00:19:24.789 --> 00:19:26.890
to stay in San Diego. It made him a bit of a

00:19:26.890 --> 00:19:29.529
hero to fans who hate seeing their teams relocated.

00:19:29.670 --> 00:19:32.529
However, and this is a massive, massive however,

00:19:32.930 --> 00:19:36.430
we cannot paint Steven Ross as some saint of

00:19:36.430 --> 00:19:38.490
integrity without looking at what's happened

00:19:38.490 --> 00:19:40.380
in the last few years. Oh, we cannot. Because

00:19:40.380 --> 00:19:42.119
for all his talk about doing things the right

00:19:42.119 --> 00:19:44.920
way, he recently got absolutely hammered by the

00:19:44.920 --> 00:19:47.200
NFL for cheating. We have to get into the controversy

00:19:47.200 --> 00:19:49.440
and complexity segment. This is where the story

00:19:49.440 --> 00:19:52.539
gets much, much darker. The Brian Flores lawsuit

00:19:52.539 --> 00:19:54.839
and the tampering investigation. Let's break

00:19:54.839 --> 00:19:56.819
this down because the details really matter here.

00:19:57.039 --> 00:19:58.940
OK, so it all started with Brian Flores, who

00:19:58.940 --> 00:20:01.200
was the head coach of the Dolphins. He was fired

00:20:01.200 --> 00:20:04.519
and he filed this scorching lawsuit against the

00:20:04.519 --> 00:20:08.460
NFL and the Dolphins alleging racial discrimination.

00:20:08.500 --> 00:20:12.170
Right. But. Buried inside that lawsuit was a

00:20:12.170 --> 00:20:14.089
grenade. The tanking allegation. The tanking

00:20:14.089 --> 00:20:16.730
allegation. He claimed that Stephen Ross offered

00:20:16.730 --> 00:20:20.410
him $100 ,000 for every single game he lost during

00:20:20.410 --> 00:20:23.150
the 2019 season. Paying to lose. Which is the

00:20:23.150 --> 00:20:26.549
cardinal sin in all of sports. If you are fixing

00:20:26.549 --> 00:20:29.210
matches. Which is what losing on purpose is.

00:20:29.390 --> 00:20:32.150
You're defrauding the fans and more importantly

00:20:32.150 --> 00:20:35.029
to the NFL, you are defrauding the gambling markets.

00:20:35.210 --> 00:20:37.029
It threatens the entire existence of the league.

00:20:37.230 --> 00:20:39.650
Absolutely. So the NFL launches this huge independent

00:20:39.650 --> 00:20:42.329
investigation. Mary Jo White, former SEC chair,

00:20:42.529 --> 00:20:45.190
leads it. What do they find? It was nuanced.

00:20:45.549 --> 00:20:48.190
The finding was very nuanced. And it's important

00:20:48.190 --> 00:20:51.170
to be precise here. The investigation found no

00:20:51.170 --> 00:20:53.509
evidence that the Dolphins intentionally lost

00:20:53.509 --> 00:20:56.549
games to improve their draft position. So he

00:20:56.549 --> 00:20:58.730
was cleared of the actual tanking. Officially,

00:20:58.730 --> 00:21:01.190
yes. Ross claimed the comment about the $100

00:21:01.190 --> 00:21:05.069
,000 was a joke made in frustration. And the

00:21:05.069 --> 00:21:06.950
investigators said they couldn't prove it was

00:21:06.950 --> 00:21:09.450
a serious offer. So they cleared him on that.

00:21:09.769 --> 00:21:12.990
However, the investigation found something else.

00:21:13.289 --> 00:21:15.309
Something they weren't even looking for initially.

00:21:15.529 --> 00:21:19.400
Campering. Massive. repeated and unprecedented

00:21:19.400 --> 00:21:22.460
tampering. Explain the difference. Why is tampering

00:21:22.460 --> 00:21:25.940
such a big deal? Tampering is illegally recruiting

00:21:25.940 --> 00:21:28.779
a player or coach who is under contract with

00:21:28.779 --> 00:21:32.579
another team. It's breaking the fundamental gentleman's

00:21:32.579 --> 00:21:34.819
agreement of the league that keeps it from being

00:21:34.819 --> 00:21:36.960
the Wild West. Okay. The investigation found

00:21:36.960 --> 00:21:39.039
that Ross and the Dolphins had impermissible

00:21:39.039 --> 00:21:41.589
communications with Tom Brady. While he was still

00:21:41.589 --> 00:21:43.670
playing for the New England Patriots. A division

00:21:43.670 --> 00:21:45.950
rival. A division rival. And then again later

00:21:45.950 --> 00:21:48.109
when he was under contract with the Tampa Bay

00:21:48.109 --> 00:21:50.750
Buccaneers. And it wasn't just like a text message,

00:21:50.769 --> 00:21:52.930
right? Oh, no. We're talking about a secret meeting

00:21:52.930 --> 00:21:55.390
on Ross's yacht in the marina. They were trying

00:21:55.390 --> 00:21:59.029
to lure Brady to Miami, possibly as a minority

00:21:59.029 --> 00:22:00.589
owner, and then eventually as the quarterback.

00:22:00.849 --> 00:22:03.900
And it wasn't just Brady. No. They also tampered

00:22:03.900 --> 00:22:06.119
with Sean Payton while he was the head coach

00:22:06.119 --> 00:22:08.079
of the New Orleans Saints, trying to get him

00:22:08.079 --> 00:22:10.619
to be their coach. So while he was publicly preaching

00:22:10.619 --> 00:22:13.039
loyalty to the fans in Oakland, he was secretly

00:22:13.039 --> 00:22:15.720
trying to poach the biggest star in football

00:22:15.720 --> 00:22:18.519
history from another team? That is the contradiction.

00:22:19.099 --> 00:22:22.380
And the punishment from the NFL was severe. They

00:22:22.380 --> 00:22:25.180
stripped the Dolphins of their 2023 first round

00:22:25.180 --> 00:22:28.480
draft pick and a 2024 third round pick. For listeners

00:22:28.480 --> 00:22:30.339
who don't follow football that closely, losing

00:22:30.339 --> 00:22:33.039
a first round pick is a disaster. It's a franchise

00:22:33.039 --> 00:22:35.500
crippling penalty. That is a potential future

00:22:35.500 --> 00:22:37.680
superstar you don't get to draft. It sets the

00:22:37.680 --> 00:22:40.539
team back for years. And Ross himself was fined

00:22:40.539 --> 00:22:44.400
$1 .5 million personally and suspended for several

00:22:44.400 --> 00:22:47.119
months. He was removed from all his NFL committees.

00:22:47.259 --> 00:22:50.009
It was a total humiliation. It brings up this

00:22:50.009 --> 00:22:52.369
really interesting psychological question for

00:22:52.369 --> 00:22:55.750
me. Here is a guy who built his entire fortune

00:22:55.750 --> 00:22:59.390
on finding legal loopholes, the tax shelters

00:22:59.390 --> 00:23:01.670
we talked about earlier. Right. Reading the rulebook

00:23:01.670 --> 00:23:04.210
better than anyone else. He reads the rulebook

00:23:04.210 --> 00:23:07.190
and finds the gray area. But in the NFL, it seems

00:23:07.190 --> 00:23:09.910
like he just decided to ignore the rulebook completely.

00:23:10.230 --> 00:23:13.130
It's the hubris of the billionaire. I mean, when

00:23:13.130 --> 00:23:16.750
you have spent 40 years literally reshaping the

00:23:16.750 --> 00:23:19.190
skyline of New York City, when you have built

00:23:19.190 --> 00:23:22.609
a city over a rail yard, you start to believe

00:23:22.609 --> 00:23:25.690
the word no is just a suggestion. That the rules

00:23:25.690 --> 00:23:28.269
apply to other people. Exactly. He wanted Tom

00:23:28.269 --> 00:23:30.170
Brady. He didn't want to wait for free agency.

00:23:30.309 --> 00:23:33.710
So he took a shot. And he missed badly. He missed.

00:23:33.809 --> 00:23:36.599
And it cost his team dearly. That tension between

00:23:36.599 --> 00:23:39.119
being a visionary and a rule breaker shows up

00:23:39.119 --> 00:23:41.779
in his politics, too. It absolutely does. Ross

00:23:41.779 --> 00:23:44.500
is the classic checkbook participant in politics.

00:23:44.759 --> 00:23:47.380
He donates to everyone. He plays both sides.

00:23:47.700 --> 00:23:49.980
Totally. He's given a lot of money to Chuck Schumer

00:23:49.980 --> 00:23:53.160
and Andrew Cuomo, powerful Democrats in New York,

00:23:53.220 --> 00:23:55.039
which you have to do if you want to build in

00:23:55.039 --> 00:23:57.859
the city. But he's also a longtime major Republican

00:23:57.859 --> 00:24:01.019
donor. And this blew up in his face in a huge

00:24:01.019 --> 00:24:05.720
way in 2019. The Hamptons fundraiser. Ross hosted

00:24:05.720 --> 00:24:09.099
this very high dollar fundraiser for Donald Trump's

00:24:09.099 --> 00:24:11.559
reelection campaign at his estate out in the

00:24:11.559 --> 00:24:13.799
Hamptons. And the backlash was immediate. But

00:24:13.799 --> 00:24:16.200
it was targeted not at him personally, but at

00:24:16.200 --> 00:24:18.819
his brands. And this is the danger of that lifestyle

00:24:18.819 --> 00:24:21.039
business model we talked about. If you just sold

00:24:21.039 --> 00:24:23.579
concrete and steel, nobody would care. Right.

00:24:23.680 --> 00:24:27.680
But Ross owns SoulCycle and Equinox. And who

00:24:27.680 --> 00:24:30.420
goes to SoulCycle? Generally, younger, urban,

00:24:30.579 --> 00:24:33.440
more liberal -leaning consumers. Exactly. The

00:24:33.440 --> 00:24:35.500
very people who were most virulently opposed

00:24:35.500 --> 00:24:38.180
to the Trump presidency. So you had this massive

00:24:38.180 --> 00:24:40.819
viral campaign to cancel memberships. People

00:24:40.819 --> 00:24:42.559
were posting screenshots of their cancellation

00:24:42.559 --> 00:24:45.259
emails. It was a complete PR nightmare for those

00:24:45.259 --> 00:24:47.799
companies. It forced the CEOs of Equinox and

00:24:47.799 --> 00:24:49.500
SoulCycle to put out these statements, basically

00:24:49.500 --> 00:24:51.460
saying, we have nothing to do with our owners'

00:24:51.539 --> 00:24:53.940
personal politics. No company profits. Go to

00:24:53.940 --> 00:24:56.059
politicians. They had to distance the brand.

00:24:56.430 --> 00:24:59.130
from the man who owns the brand. A very awkward

00:24:59.130 --> 00:25:01.509
position to be in. It's a tricky needle to thread.

00:25:01.769 --> 00:25:04.289
And Ross basically said, look, I've known Trump

00:25:04.289 --> 00:25:06.549
for years. I like his economic policies. Get

00:25:06.549 --> 00:25:09.150
over it. He didn't apologize. No, he didn't.

00:25:09.150 --> 00:25:13.789
He doubled down. In 2021, his super PAC spent.

00:25:14.319 --> 00:25:17.000
a ton of money to oppose progressive Democrats

00:25:17.000 --> 00:25:19.119
who are running for office in New York City.

00:25:19.220 --> 00:25:22.400
So he's not backing down. Not at all. He operates

00:25:22.400 --> 00:25:24.900
on the belief that his money gives him a voice

00:25:24.900 --> 00:25:27.359
and he's going to use it regardless of what the

00:25:27.359 --> 00:25:29.799
SoulCycle writers in Soho think. Which makes

00:25:29.799 --> 00:25:32.799
his philanthropy even more confusing or complex.

00:25:33.119 --> 00:25:35.420
If you look at where he gives his money, it doesn't

00:25:35.420 --> 00:25:37.539
align with the conservative billionaire stereotype

00:25:37.539 --> 00:25:40.759
at all. No, it really doesn't. He is the single

00:25:40.759 --> 00:25:43.279
largest donor in the entire history of the University

00:25:43.279 --> 00:25:45.420
of Michigan. The largest ever. He's given nearly

00:25:45.420 --> 00:25:48.720
half a billion dollars. The number is $478 million.

00:25:49.140 --> 00:25:51.140
The business school is named after him, the Ross

00:25:51.140 --> 00:25:53.119
School of Business. After a $100 million gift.

00:25:53.920 --> 00:25:56.420
But it's not just buildings. Look at an organization

00:25:56.420 --> 00:25:59.579
he founded called RISE. RISE, the Ross Initiative

00:25:59.579 --> 00:26:02.940
in Sports for Equality. He founded this in 2015.

00:26:03.400 --> 00:26:06.240
The mission is specifically to fight racism and

00:26:06.240 --> 00:26:08.420
promote social justice within the sports industry.

00:26:09.250 --> 00:26:11.289
He's put millions and millions of his own dollars

00:26:11.289 --> 00:26:14.029
into this. He partners with the NAACP, with all

00:26:14.029 --> 00:26:15.869
the major leaguers. OK, so let me just get this

00:26:15.869 --> 00:26:18.990
straight. He funds a massive anti -racism initiative.

00:26:19.170 --> 00:26:21.809
Yes. But he's a major supporter of Donald Trump,

00:26:21.910 --> 00:26:24.769
who many people accuse of racist rhetoric. Yes,

00:26:24.769 --> 00:26:27.509
yes. And he gets sued by his own black head coach

00:26:27.509 --> 00:26:29.569
for racial discrimination in hiring practices.

00:26:29.869 --> 00:26:32.630
Yes, that too. It's messy. It's a flat out contradiction.

00:26:32.990 --> 00:26:35.470
Or it's compartmentalization. I think Ross views

00:26:35.470 --> 00:26:38.700
these things as separate silos in his life. In

00:26:38.700 --> 00:26:40.700
his mind, rise is a good thing he's doing for

00:26:40.700 --> 00:26:42.940
the world. The Brian Flores lawsuit is just a

00:26:42.940 --> 00:26:45.099
business dispute. The Trump support is about

00:26:45.099 --> 00:26:47.819
tax policy and economic growth. And he doesn't

00:26:47.819 --> 00:26:49.960
seem to feel the cognitive dissonance that the

00:26:49.960 --> 00:26:52.180
rest of us feel looking at it. Doesn't seem to

00:26:52.180 --> 00:26:55.099
bother him. He also gave $100 million to the

00:26:55.099 --> 00:26:57.779
World Resources Institute to create the WRI Ross

00:26:57.779 --> 00:26:59.980
Center for Sustainable Cities. So he's a green

00:26:59.980 --> 00:27:03.319
crusader. An anti -racism advocate, a Trump supporter,

00:27:03.460 --> 00:27:07.160
and a ruthless real estate tycoon all at the

00:27:07.160 --> 00:27:10.069
same time. He is a city state. That's the best

00:27:10.069 --> 00:27:12.309
way to describe him. That's a compelling, if

00:27:12.309 --> 00:27:14.849
slightly terrifying, way to look at it. He operates

00:27:14.849 --> 00:27:17.940
like a sovereign nation. A nation has a defense

00:27:17.940 --> 00:27:20.880
budget, a foreign aid budget, a trade policy.

00:27:21.319 --> 00:27:24.079
They don't always align perfectly from an ethical

00:27:24.079 --> 00:27:26.420
standpoint, but they all serve the interests

00:27:26.420 --> 00:27:28.900
of the state. And Stephen Ross is the state.

00:27:29.079 --> 00:27:31.779
It's the reality of that level of wealth. You

00:27:31.779 --> 00:27:34.359
stop being a person and you start being an economy.

00:27:34.539 --> 00:27:36.920
That's well said. So we've been talking for a

00:27:36.920 --> 00:27:39.700
while now. We've dissected the tax schemes, the

00:27:39.700 --> 00:27:42.460
engineering marvels, the stadium gambles, the

00:27:42.460 --> 00:27:45.160
scandals. If I'm a listener trying to wrap my

00:27:45.160 --> 00:27:47.400
head around Steve, in him, Ross, what is the

00:27:47.400 --> 00:27:49.799
one thing I should take away from all this? I

00:27:49.799 --> 00:27:51.480
think the biggest lesson is about the leverage

00:27:51.480 --> 00:27:54.240
of technical mastery. Ross didn't win because

00:27:54.240 --> 00:27:56.720
he had the best smile or the firmest handshake.

00:27:56.819 --> 00:27:59.380
It wasn't about personality. No. He won because

00:27:59.380 --> 00:28:02.920
he understood the tax code of 1972 better than

00:28:02.920 --> 00:28:04.619
the other guys at the table. He read the fine

00:28:04.619 --> 00:28:07.930
print. He weaponized the fine print. He realized

00:28:07.930 --> 00:28:10.390
that the government incentives, whether it was

00:28:10.390 --> 00:28:12.809
for affordable housing in the 70s or for the

00:28:12.809 --> 00:28:15.549
massive tax breaks for Hudson Yards in the 2010s,

00:28:15.549 --> 00:28:18.910
were the engine. He didn't fight the current.

00:28:19.049 --> 00:28:21.230
He just found out where the river was flowing

00:28:21.230 --> 00:28:23.990
and built a dam to catch all the money. It's

00:28:23.990 --> 00:28:26.549
a powerful reminder that sometimes the most creative

00:28:26.549 --> 00:28:29.789
tool in business isn't the marketing deck. It's

00:28:29.789 --> 00:28:32.450
the legal brief or the tax code. Absolutely.

00:28:32.509 --> 00:28:35.430
And the second big takeaway is that idea of placemaking.

00:28:36.179 --> 00:28:39.059
Don't just sell a product. Create the ecosystem

00:28:39.059 --> 00:28:41.319
that makes the product necessary. Don't just

00:28:41.319 --> 00:28:44.140
buy a team. Build a world where the team is the

00:28:44.140 --> 00:28:46.599
center of gravity for entertainment, for sports,

00:28:46.619 --> 00:28:48.299
for everything. But I want to leave with one

00:28:48.299 --> 00:28:50.119
final thought on that rule breaker mentality.

00:28:50.740 --> 00:28:52.839
We started this whole conversation with him getting

00:28:52.839 --> 00:28:55.359
fired for clashing with the boss. Right. He then

00:28:55.359 --> 00:28:57.799
spent the next 50 years ensuring he never had

00:28:57.799 --> 00:29:00.339
a boss ever again. He became the ultimate boss.

00:29:00.779 --> 00:29:04.140
But the NFL tampering scandal proves that even

00:29:04.140 --> 00:29:07.119
the ultimate boss hits a wall eventually. The

00:29:07.119 --> 00:29:09.559
rules finally caught up to him. And it makes

00:29:09.559 --> 00:29:13.859
me wonder, is that risk taking? That willingness

00:29:13.859 --> 00:29:17.140
to tamper, to push, to ignore the word no? Is

00:29:17.140 --> 00:29:19.900
that the fatal flaw in his character? Or is it

00:29:19.900 --> 00:29:22.539
the only reason Hudson Yards even exists? Can

00:29:22.539 --> 00:29:25.259
you have the vision to build a city on a platform

00:29:25.259 --> 00:29:27.500
without also having the arrogance to think you're

00:29:27.500 --> 00:29:29.920
above the law? I don't think you can. I think

00:29:29.920 --> 00:29:32.259
they are two sides of the exact same coin. The

00:29:32.259 --> 00:29:34.839
audacity that it takes to look at an open rail

00:29:34.839 --> 00:29:36.700
yard and say, I'm going to build a neighborhood

00:29:36.700 --> 00:29:39.380
there is the same audacity that makes you think

00:29:39.380 --> 00:29:41.240
you can just tap up Tom Brady on your yacht and

00:29:41.240 --> 00:29:43.019
get away with it. You can't buy one without the

00:29:43.019 --> 00:29:45.359
other. A complicated legacy for a complicated

00:29:45.359 --> 00:29:49.200
man. Stephen Ross, the tax attorney who rebuilt

00:29:49.200 --> 00:29:52.640
New York. And gave us a lot to talk about today.

00:29:52.960 --> 00:29:54.740
Thanks for diving in with us. There is so much

00:29:54.740 --> 00:29:57.180
more detail in the show notes. We've got links

00:29:57.180 --> 00:29:59.339
to the Mary Jo White report, breakdowns of the

00:29:59.339 --> 00:30:01.460
tax structures, the whole history of Hudson Yards.

00:30:01.480 --> 00:30:03.000
Go check those out if you really want to geek

00:30:03.000 --> 00:30:04.859
out on the numbers. Definitely worth a read.

00:30:04.980 --> 00:30:07.940
We'll see you on the next Deep Dive. See you

00:30:07.940 --> 00:30:08.039
then.
