Welcome back to the Deep Dive. Today we are taking
a stack of sources, articles, legal filings,
financial breakdowns about a single individual.
Yeah. And we're going to try to answer a question
that honestly, it just baffles me. What's that?
How does a man get fired from a corporate job
at age 32 with no money, forced to borrow 10
grand from his mother just to pay rent? Right.
And end up reshaping the entire skyline of New
York City and owning an NFL franchise? It sounds
like fiction. I mean, if you pitch this as a
screenplay, they tell you the second act is just
too unrealistic. Right. But we are talking about
Stephen M. Ross. Stephen M. Ross. Yeah. The man,
the myth, the mega developer. The man behind
related companies, Hudson Yards, the Miami Dolphins.
But I want to be real. clear right off the bat.
This isn't just a biography. We aren't here to
just list the buildings he bought or his net
worth. Right. If we just list his assets, we
completely missed the point. We're here to understand
the anatomy of a mega developer. The anatomy.
I like that. We need to look at how tax law,
real estate, and professional sports ownership
intersect. Because when you peel back the layers
on Ross, you realize... These aren't separate
businesses. No. They are all pieces of one massive
self -sustaining ecosystem. That's what jumped
out at me in all the research. He's not just
a guy who likes football and also happens to
like skyscrapers. There is a very specific machinery
underneath it all. It's all about leverage. It's
about incentives. And it's about understanding
the rules better than anyone else in the room.
Specifically. The boring rules. The tax code.
The tax code. That's the secret. We're going
to get deep into the weeds on that because I
think that's the secret sauce here. We have a
lot to cover. A ton. We've got the origin story
in Detroit, the aha moment with affordable housing,
the massive gamble of Hudson Yards. The whole
Miami Dolphins saga. And of course, the controversies,
which are significant. Oh, yeah. But let's start
at the beginning. Because before he was a billionaire,
he was just a kid in Detroit. Born in 1940. A
Jewish family in Detroit. He goes to Mumford
High School. And I think, to understand Ross,
you really have to look at his education. Okay.
It's not the typical path for a developer. Not
at all. I was looking at this timeline. It's
pretty exhaustive. He starts at the University
of Florida. Right. Then transfers to the University
of Michigan, which, you know, becomes this huge
part of his life later on. Gets a BBA in 1962.
Standard stuff so far. Then he goes to Wayne
State for a law degree. But then, and this is
the part where I really paused, he goes to NYU.
For a master of laws in taxation and LLM. Taxation.
Okay, help me out here. Usually when we talk
about real estate tycoons, we're talking about
these guys with big personalities, sales guys,
maybe architects. Guys who can sell a vision.
Exactly. A master's degree in taxation sounds,
well, it sounds dry. It is dry. It's incredibly
dry. But that is the superpower. See, most people
look at a building and see bricks, glass, maybe
a nice lobby. They see rental income. Right.
They see the physical thing. Ross looks at a
building and sees a depreciation schedule. He
sees tax credits. He sees a vehicle for sheltering
income. So he's seeing the matrix code behind
the building. He's seeing the matrix code. That's
it. He's looking at the invisible financial structure
that makes the physical structure possible. And
that specific degree, that specialized knowledge
of the tax code is the tool that eventually builds
the entire empire. But it didn't happen immediately.
Oh, no. Not even close. Right. Because first,
he has to fail. And he fails hard. He moves to
New York, works at Bear Stearns in corporate
finance. This is the late 60s, early 70s. It's
a prestigious job. I mean, Bear Stearns, but
Ross. While all the reports suggest he wasn't
great at taking orders. Doesn't play well with
others. He had a certain arrogance or maybe just
a conviction that he knew better. So in 1972,
he gets into a big conflict with a superior.
And it's not just, you know, a slap on the wrist.
No. He gets fired. I want to just pause on this
moment because it's so easy to gloss over in
retrospect. It's 1972. You are 32 years old.
Yeah. You have a law degree, a master's degree.
You're in the most competitive city on earth
and you just got canned. Utterly terrifying.
That is a terrifying position to be in. It is.
And he wasn't sitting on some pile of cash. The
sources all say he literally didn't have the
liquidity to maintain his lifestyle. He had to
go to his mother. His mom. And borrow $10 ,000.
Which, accounting for inflation, is about $67
,000 today. So it's a keep the lights on loan.
It's not seed capital for an empire. No, it's
survival money. It's please don't get evicted
from my apartment money. And this is the pivot
point. This is where most people would polish
the resume, maybe shave the mustache and go interview
at another bank. Right. Get back on the horse.
Ross decides he is done answering to people.
He decides to leverage the one thing he has that
others don't. The tax degree. That deep technical
knowledge of tax law. And this brings us to the
first big chapter of his success, affordable
housing. But not, he wasn't building it, right?
He was structuring it. Correct. He wasn't the
guy with the hard hat. Not yet. I need you to
explain this to me like I'm five years old. Or
maybe. Maybe like I'm a dentist in 1972 with
some extra cash. What exactly was Ross selling?
Because he wasn't pouring concrete yet. Okay.
Okay. Let's role play. You're a wealthy dentist
or a partner at a law firm in 1972. You're making,
say, $100 ,000 a year, which is a lot of money
back then. A huge amount. But the top marginal
tax rate in the 70s was incredibly high. Over
50 percent, sometimes up to 70 percent. So the
government is just taking this huge chunk of
my money. I'm looking for a way to keep it. You're
desperate to keep it. Exactly. So enter Stephen
Ross. He comes to you and says, I have an investment
opportunity in government subsidized affordable
housing. OK, that doesn't sound very sexy. Affordable
housing? No, it doesn't sound like a big moneymaker.
Rents are capped. But Ross explains the tax side
of it. The federal government wants this housing
built, so they offer massive incentives. Specifically.
they allow you to accelerate depreciation. Depreciation.
Okay, so on paper, the building is losing value.
On paper, yes. Even if it's appreciating in the
real world. So Ross structures a deal where you,
the dentist, put in, say, $10 ,000 cash. Okay,
I'm in for $10 ,000. But because of how the tax
laws worked in, that investment allows you to
claim a loss on your taxes that is much, much
larger than your actual cash investment. So it's
a paper loss. It's a paper loss. Let's say you
can claim a $40 ,000 loss on paper. You take
that $40 ,000 loss, you apply it against your
dentist income, and suddenly that $20 ,000 you
were going to pay to the IRS, it's gone. You
owe them nothing. Wait, so I give Ross $10 ,000
and I save $20 ,000 in taxes? Yes. I've just
made money instantly by signing a piece of paper.
Precisely. You made a 100 % return on your money
via the tax code, regardless of whether the building
ever collects a single dime in rent. Wow. Ross
wasn't selling apartments. He was selling tax
shelters. He was syndicating these deals, pooling
money from all these wealthy investors who needed
to hide income, and then using that money to
back the actual affordable housing developers.
That is, well it's genius. It's completely genius.
And it explains why that tax degree was so important.
Everything. A regular developer wouldn't know
how to structure the partnership to maximize
those write -offs. No way. He monetized the boring
stuff. He realized that the government was effectively
handing out free money to encourage this kind
of housing. But you needed a translator to access
it. And he was the translator. He was the Rosetta
Stone for tax shelters. Yeah. In his first year,
1972, the same year he was fired and broke, he
made $150 ,000. That is a massive amount of money
for 1972. That's top 1 % income, like immediately.
Immediately. And that is the birth of related
companies. Which was originally called Related
Housing Company. Exactly. It was built entirely
on this specific niche. Subsidized, low to moderate
income housing. For years, he became one of the
biggest affordable housing developers in the
country. It's just fascinating because today
the brand related means the exact opposite. The
total opposite. It means $10 million condos,
Equinox gyms, Hudson Yards luxury. It's the definition
of elite. How does he bridge that gap? How do
you go from Section 8 housing to selling penthouses
to oligarchs? It's two things, capital and confidence.
The affordable housing business is great because
it's really low risk. The government guarantees
the rent. Built in safety net. Right. And it
generates steady cash flow. So it built his balance
sheet. By the 1980s, he has enough of his own
money to start taking bigger and bigger risks.
And he starts moving into Manhattan. He starts
moving into Manhattan. He starts hiring star
architects, you know, famous architects like
Robert A .M. Stern. He wants his buildings to
be landmarks. He moves from need to want. That's
a great way to put it. Affordable housing is
a need product. Luxury real estate is a want
product. An aspirational product. Totally. And
Ross realized that if you wanted to leave a mark
on the skyline, and make billions instead of
millions. He had to capture that want market.
Which leads us to the behemoth. I mean, the portfolio
today is valued at over $60 billion. It's staggering.
They are everywhere. London, Abu Dhabi, LA, Chicago.
But the crown jewel, the thing that I think will
define his obituary one day, is Hudson Yards.
The city within a city. I walked through there
recently. It is just, it's overwhelming. It feels
like a different planet compared to the rest
of Hell's Kitchen. It does. But the backstory
of just building it is insane. It is the largest
private real estate development in the history
of the United States. Largest? Ever. 28 acres
on the west side of Manhattan. But here is the
kicker. And this is what blows people's minds.
There was no land there. What do you mean there
was no land? I've stood on it. What you were
standing on was man -made. It was an active Long
Island Railroad train yard. Dozens of tracks
with trains running 2047. To build Hudson Yards,
Ross had to build a massive platform over the
trains. Wait, wait, wait. So the skyscrapers,
the vessel, the mall, it's all sitting on a giant
table. Essentially, yes. Yeah. A ridiculously
complex and expensive table. They had to drill
these huge support pillars called caissons down
into the bedrock between the train tracks. While
the trains were running. While the trains were
running. Right. Without hitting the trains or
the high voltage lines. And then they had to
build a massive concrete and steel deck on top
of those pillars. And then they could start building
the hundred story buildings on top of that deck.
The engineering risk alone is staggering. It's
mind boggling. And what about the cost? Just
the platform. Just to create. The fake ground
cost? Roughly a billion dollars per acre. A billion
dollars an acre? A billion. Just to get to ground
zero, before you even lay a single brick for
a lobby, that sounds like financial suicide.
Why would anyone ever do that? Because if you
pull it off, you own an entire neighborhood in
Manhattan. Think about it. Usually developers
fight over one lot, one corner. A single building.
Right. Ross manufactured 28 acres of prime real
estate out of thin air. But to make it pay off,
he needed tenants and not just any tenants. He
needed companies that could pay top tier premium
rents to cover those astronomical construction
costs. And this brings us to this placemaking
concept. I read this story about Coach, the handbag
company, and I think it perfectly illustrates
how Ross operates. The Coach story is the textbook
example of Ross's dealmaking style. It really
is. He needed an anchor tenant. The first domino.
Exactly. Without a big name, no one else comes.
So he wanted Coach to move their global headquarters
to Hudson Yards. Coach was, you know, skeptical.
Of course. Why would they move to a noisy construction
zone over a rail yard? It's far west. It's totally
unproven. Right. So Ross didn't just offer them
a good lease. He offered to alter the physical
reality of the building for them. What does that
mean? Coach wanted a specific kind of internal
flow for their creative teams, this very open,
collaborative feel. So Ross redesigned the tower
to include a massive multi -story atrium right
in the middle of the building. In the middle?
Yes, specifically for them. He carved out what
would have been tens of thousands of square feet
of valuable, rentable office space. So he sacrificed
rent money just to create a vibe for one tenant.
Yes. He sacrificed rentable space to create a
wow factor that closed the deal. And once Coach
signed on the dotted line... The entire narrative
changed. Suddenly, Hudson Yards wasn't a risky
rail yard project. It was the new home of American
luxury fashion. And then everyone else follows.
Then L 'Oreal came. Then SAP came. Then the private
equity giant KKR came. It's the domino effect.
And this is where we see the difference between
just being a landlord and being a placemaker.
It's a huge difference. A landlord rents you
four walls and a floor. A placemaker curates
an entire environment. Ross didn't just build
offices. He built The Shed, a world -class cultural
center. He built The Vessel, that giant honeycomb
staircase sculpture that everyone takes pictures
of. He put in restaurants from Thomas Keller
and Jose Andres, high -end destination dining.
And he put in Equinox. Right. And this is crucial.
This is the ecosystem part. Related Companies
is a major investor in Equinox Fitness and SoulCycle.
So he builds the condo you live in. He builds
the office you work in. And he owns the gym where
you work out downstairs. And the restaurant where
you have dinner. He captures every single slice
of your day. It's the vertical integration of
the human lifestyle. It's almost like living
on a cruise ship that never leaves the dock.
You never have to leave the Stephen Ross ecosystem.
That is the goal. You control the environment.
You control the spend. Now, speaking of control.
We have to pivot. We have to go to the other
massive pillar of his life. Okay. We've covered
the tax attorney and the builder. Now we have
to talk about the sports tycoon. The Miami Dolphins.
This feels like a totally different world, but
you argued earlier that it's the same muscle
group. How does that work? It's all about asset
appreciation and leverage. So Russ buys 95 %
of the Dolphins in the stadium for about $1 .1
billion around 2008, 2009. Okay. And people thought,
OK, another rich guy buys a toy. But Ross didn't
treat it like a toy. He treated it like a distressed
real estate asset. And the stadium was aging,
right? It wasn't a great venue. It was a concrete
bowl. It had been beaten up by the Florida sun.
It wasn't generating the kind of revenue it could.
Now, usually, this is the part of the story where
the billionaire owner goes to the city council.
With his handout. With his handout. It says,
Build me a brand new shiny stadium. Or I'm moving
the team to Los Angeles or San Antonio or wherever.
We see it constantly. It's happening in Buffalo,
Tennessee, Vegas. It's the standard playbook.
It is the playbook. And Ross tried it. In 2013,
he went to the state of Florida and asked for
public money. About $3 million a year for 30
years for renovations. Yeah, and they said no.
The Florida legislature shut him down. Flatly.
So typically, this is where the owner throws
a tantrum. Fine, I'm taking my team and leaving.
Ross didn't. He did something that absolutely
shocked the NFL community. What did he do? He
reached into his own pocket and spent roughly
$500 million of his own money to completely renovate
Hard Rock Stadium. Half a billion dollars. Now,
I have to be skeptical here. Why? Is he just
a benevolent fan who loves the city of Miami?
Or is there a cold, hard, calculated reason to
spend $500 million of your own cash? Oh, it's
absolutely calculated, 100%. Think about it.
If you take public money, you have public strings
attached. The city wants a cut of the parking
revenue. The county wants a say in what events
you host. The state wants to know why you're
charging so much for a beer. But if you pay for
it yourself. You own the revenue streams, all
of them. And Ross had a vision that went... way,
way beyond just football. He looked at that stadium
and realized that an NFL stadium sits empty 350
days a year. It's a terribly wasted asset. It's
a terrible use of real estate. Exactly. So he
renovated the stadium to make it a global entertainment
hub. He put a roof over the seats. He upgraded
all the suites. And he brought in tennis. He
brought in the Miami Open tennis tournament.
He poached it from its longtime home in Key Biscayne.
He built a permanent world -class tennis complex
on the grounds of the football stadium. And then...
The big one. Formula One. The Miami Grand Prix.
This is a masterclass in logistics and, frankly,
in lobbying. He managed to secure a 10 -year
exclusive contract with F1. Which is a huge deal.
Huge. But the problem was, where do you race?
He couldn't shut down downtown Miami like they
do in Monaco or Singapore. The local opposition
was just too strong. So he looked at his own
parking lot. He looked at the vast expanse of
land surrounding Hard Rock Stadium. And critics
laughed at first. They said, you're going to
race these incredible F1 cars in a parking lot.
Right. But Ross saw a campus. He built a temporary,
purpose -built circuit. They call it the Miami
International Autodrome. that winds all around
the stadium. I looked into the engineering of
this. It's not just painting lines on asphalt.
No. F1 cars create immense G -forces and suction.
They had to lay specialized, high -grade racing
asphalt on top of the existing grounds, ensure
drainage, build FIA -certified safety barriers.
And then a few weeks later, turn it all back
into a parking lot for football season. A logistical
nightmare. A nightmare. But it worked. The event
is a massive cash cow. VIP tickets cost Thousands
and thousands of dollars. And because Ross owns
the stadium and the land and paid for the upgrades
himself. He captures all of that revenue. He
captures the lion's share. He turned a football
field into a 365 -day entertainment district
that hosts a Super Bowl, a college football championship,
a tennis major, and a Formula One race. It connects
right back to Hudson Yards. It's placemaking
again. He's not selling a race. He's selling
the Miami Grand Prix experience. With the yachts
and the fake marina and the celebrity clubs,
yes. He sells the sizzle, and the state comes
along for the ride. That's his old model. But
he's also a bit of a maverick within that exclusive
NFL owners circle, right? He doesn't always just
vote with a pack. No, he really doesn't. The
best example of this is the Raiders vote back
in 2017. OK. The NFL owners voted 31 to 1 to
approve the Oakland Raiders moving to Las Vegas.
And Ross was the one. He was the lone dissenter.
The only no vote. Why? I mean, Las Vegas is a
goldmine. Why would a guy who loves money so
much vote against moving a team to Vegas? His
public reasoning was that he believed the owners
hadn't done enough to try to keep the team in
Oakland. He felt that there was a social contract
with the fan base. Interesting. He thought that
moving teams too frequently, and you have to
remember the Rams and Chargers had just moved
to L .A., eroded the long -term value of the
NFL brand itself. He was worried about fan loyalty.
He basically said, if we treat these teams like
interchangeable widgets that we can just move
around a chessboard, eventually the fans will
stop caring. That's surprisingly principled,
or at least it's a very long -term view versus
a short -term cash grab. It is. He also threw
some not -so -subtle shade at the Chargers' ownership,
suggesting they didn't really try hard enough
to stay in San Diego. It made him a bit of a
hero to fans who hate seeing their teams relocated.
However, and this is a massive, massive however,
we cannot paint Steven Ross as some saint of
integrity without looking at what's happened
in the last few years. Oh, we cannot. Because
for all his talk about doing things the right
way, he recently got absolutely hammered by the
NFL for cheating. We have to get into the controversy
and complexity segment. This is where the story
gets much, much darker. The Brian Flores lawsuit
and the tampering investigation. Let's break
this down because the details really matter here.
OK, so it all started with Brian Flores, who
was the head coach of the Dolphins. He was fired
and he filed this scorching lawsuit against the
NFL and the Dolphins alleging racial discrimination.
Right. But. Buried inside that lawsuit was a
grenade. The tanking allegation. The tanking
allegation. He claimed that Stephen Ross offered
him $100 ,000 for every single game he lost during
the 2019 season. Paying to lose. Which is the
cardinal sin in all of sports. If you are fixing
matches. Which is what losing on purpose is.
You're defrauding the fans and more importantly
to the NFL, you are defrauding the gambling markets.
It threatens the entire existence of the league.
Absolutely. So the NFL launches this huge independent
investigation. Mary Jo White, former SEC chair,
leads it. What do they find? It was nuanced.
The finding was very nuanced. And it's important
to be precise here. The investigation found no
evidence that the Dolphins intentionally lost
games to improve their draft position. So he
was cleared of the actual tanking. Officially,
yes. Ross claimed the comment about the $100
,000 was a joke made in frustration. And the
investigators said they couldn't prove it was
a serious offer. So they cleared him on that.
However, the investigation found something else.
Something they weren't even looking for initially.
Campering. Massive. repeated and unprecedented
tampering. Explain the difference. Why is tampering
such a big deal? Tampering is illegally recruiting
a player or coach who is under contract with
another team. It's breaking the fundamental gentleman's
agreement of the league that keeps it from being
the Wild West. Okay. The investigation found
that Ross and the Dolphins had impermissible
communications with Tom Brady. While he was still
playing for the New England Patriots. A division
rival. A division rival. And then again later
when he was under contract with the Tampa Bay
Buccaneers. And it wasn't just like a text message,
right? Oh, no. We're talking about a secret meeting
on Ross's yacht in the marina. They were trying
to lure Brady to Miami, possibly as a minority
owner, and then eventually as the quarterback.
And it wasn't just Brady. No. They also tampered
with Sean Payton while he was the head coach
of the New Orleans Saints, trying to get him
to be their coach. So while he was publicly preaching
loyalty to the fans in Oakland, he was secretly
trying to poach the biggest star in football
history from another team? That is the contradiction.
And the punishment from the NFL was severe. They
stripped the Dolphins of their 2023 first round
draft pick and a 2024 third round pick. For listeners
who don't follow football that closely, losing
a first round pick is a disaster. It's a franchise
crippling penalty. That is a potential future
superstar you don't get to draft. It sets the
team back for years. And Ross himself was fined
$1 .5 million personally and suspended for several
months. He was removed from all his NFL committees.
It was a total humiliation. It brings up this
really interesting psychological question for
me. Here is a guy who built his entire fortune
on finding legal loopholes, the tax shelters
we talked about earlier. Right. Reading the rulebook
better than anyone else. He reads the rulebook
and finds the gray area. But in the NFL, it seems
like he just decided to ignore the rulebook completely.
It's the hubris of the billionaire. I mean, when
you have spent 40 years literally reshaping the
skyline of New York City, when you have built
a city over a rail yard, you start to believe
the word no is just a suggestion. That the rules
apply to other people. Exactly. He wanted Tom
Brady. He didn't want to wait for free agency.
So he took a shot. And he missed badly. He missed.
And it cost his team dearly. That tension between
being a visionary and a rule breaker shows up
in his politics, too. It absolutely does. Ross
is the classic checkbook participant in politics.
He donates to everyone. He plays both sides.
Totally. He's given a lot of money to Chuck Schumer
and Andrew Cuomo, powerful Democrats in New York,
which you have to do if you want to build in
the city. But he's also a longtime major Republican
donor. And this blew up in his face in a huge
way in 2019. The Hamptons fundraiser. Ross hosted
this very high dollar fundraiser for Donald Trump's
reelection campaign at his estate out in the
Hamptons. And the backlash was immediate. But
it was targeted not at him personally, but at
his brands. And this is the danger of that lifestyle
business model we talked about. If you just sold
concrete and steel, nobody would care. Right.
But Ross owns SoulCycle and Equinox. And who
goes to SoulCycle? Generally, younger, urban,
more liberal -leaning consumers. Exactly. The
very people who were most virulently opposed
to the Trump presidency. So you had this massive
viral campaign to cancel memberships. People
were posting screenshots of their cancellation
emails. It was a complete PR nightmare for those
companies. It forced the CEOs of Equinox and
SoulCycle to put out these statements, basically
saying, we have nothing to do with our owners'
personal politics. No company profits. Go to
politicians. They had to distance the brand.
from the man who owns the brand. A very awkward
position to be in. It's a tricky needle to thread.
And Ross basically said, look, I've known Trump
for years. I like his economic policies. Get
over it. He didn't apologize. No, he didn't.
He doubled down. In 2021, his super PAC spent.
a ton of money to oppose progressive Democrats
who are running for office in New York City.
So he's not backing down. Not at all. He operates
on the belief that his money gives him a voice
and he's going to use it regardless of what the
SoulCycle writers in Soho think. Which makes
his philanthropy even more confusing or complex.
If you look at where he gives his money, it doesn't
align with the conservative billionaire stereotype
at all. No, it really doesn't. He is the single
largest donor in the entire history of the University
of Michigan. The largest ever. He's given nearly
half a billion dollars. The number is $478 million.
The business school is named after him, the Ross
School of Business. After a $100 million gift.
But it's not just buildings. Look at an organization
he founded called RISE. RISE, the Ross Initiative
in Sports for Equality. He founded this in 2015.
The mission is specifically to fight racism and
promote social justice within the sports industry.
He's put millions and millions of his own dollars
into this. He partners with the NAACP, with all
the major leaguers. OK, so let me just get this
straight. He funds a massive anti -racism initiative.
Yes. But he's a major supporter of Donald Trump,
who many people accuse of racist rhetoric. Yes,
yes. And he gets sued by his own black head coach
for racial discrimination in hiring practices.
Yes, that too. It's messy. It's a flat out contradiction.
Or it's compartmentalization. I think Ross views
these things as separate silos in his life. In
his mind, rise is a good thing he's doing for
the world. The Brian Flores lawsuit is just a
business dispute. The Trump support is about
tax policy and economic growth. And he doesn't
seem to feel the cognitive dissonance that the
rest of us feel looking at it. Doesn't seem to
bother him. He also gave $100 million to the
World Resources Institute to create the WRI Ross
Center for Sustainable Cities. So he's a green
crusader. An anti -racism advocate, a Trump supporter,
and a ruthless real estate tycoon all at the
same time. He is a city state. That's the best
way to describe him. That's a compelling, if
slightly terrifying, way to look at it. He operates
like a sovereign nation. A nation has a defense
budget, a foreign aid budget, a trade policy.
They don't always align perfectly from an ethical
standpoint, but they all serve the interests
of the state. And Stephen Ross is the state.
It's the reality of that level of wealth. You
stop being a person and you start being an economy.
That's well said. So we've been talking for a
while now. We've dissected the tax schemes, the
engineering marvels, the stadium gambles, the
scandals. If I'm a listener trying to wrap my
head around Steve, in him, Ross, what is the
one thing I should take away from all this? I
think the biggest lesson is about the leverage
of technical mastery. Ross didn't win because
he had the best smile or the firmest handshake.
It wasn't about personality. No. He won because
he understood the tax code of 1972 better than
the other guys at the table. He read the fine
print. He weaponized the fine print. He realized
that the government incentives, whether it was
for affordable housing in the 70s or for the
massive tax breaks for Hudson Yards in the 2010s,
were the engine. He didn't fight the current.
He just found out where the river was flowing
and built a dam to catch all the money. It's
a powerful reminder that sometimes the most creative
tool in business isn't the marketing deck. It's
the legal brief or the tax code. Absolutely.
And the second big takeaway is that idea of placemaking.
Don't just sell a product. Create the ecosystem
that makes the product necessary. Don't just
buy a team. Build a world where the team is the
center of gravity for entertainment, for sports,
for everything. But I want to leave with one
final thought on that rule breaker mentality.
We started this whole conversation with him getting
fired for clashing with the boss. Right. He then
spent the next 50 years ensuring he never had
a boss ever again. He became the ultimate boss.
But the NFL tampering scandal proves that even
the ultimate boss hits a wall eventually. The
rules finally caught up to him. And it makes
me wonder, is that risk taking? That willingness
to tamper, to push, to ignore the word no? Is
that the fatal flaw in his character? Or is it
the only reason Hudson Yards even exists? Can
you have the vision to build a city on a platform
without also having the arrogance to think you're
above the law? I don't think you can. I think
they are two sides of the exact same coin. The
audacity that it takes to look at an open rail
yard and say, I'm going to build a neighborhood
there is the same audacity that makes you think
you can just tap up Tom Brady on your yacht and
get away with it. You can't buy one without the
other. A complicated legacy for a complicated
man. Stephen Ross, the tax attorney who rebuilt
New York. And gave us a lot to talk about today.
Thanks for diving in with us. There is so much
more detail in the show notes. We've got links
to the Mary Jo White report, breakdowns of the
tax structures, the whole history of Hudson Yards.
Go check those out if you really want to geek
out on the numbers. Definitely worth a read.
We'll see you on the next Deep Dive. See you
then.