Okay, I want you to picture the color green.
And I don't just mean the color of money. Though,
uh, spoiler alert. We are definitely going to
talk about a boatload of cash today. A literal
boatload. I'm talking about that specific Kelly
Green. I'm talking about, you know, that leprechaun
lucky and clouds of cigar smoke and that bizarre
floor that makes the ball bounce sideways. You're
talking about the Boston Celtics. We are unpacking
the legacy of the Boston Celtics today. And it
really is the story of the NBA in a lot of ways.
Yeah. I mean, if you just took the Celtics out
of the history books, the league would look completely
different. Oh, completely. talking about a franchise
that as of 2024, finally broke that tie with
the Lakers. Stood alone with 18 championships.
They've got more wins than any other team in
history. It's a resume that, frankly, reads like
fiction. It does. But here's the thing that really
grabbed me and why we're doing this deep dive
right now. It's not just the trophies. It's the
valuation. We're recording this looking back
at May of 2025, which feels like just yesterday,
when the team was sold to William Chisholm and
his private equity group. For 6 .1. billion dollars
6 .1 billion with a b I tried to visualize that
amount of money earlier today and I just. I got
a headache. It's a staggering number. And at
the moment the Inc. tried, it was the highest
price ever paid for a North American sports franchise.
Right. Now, we know the market is just insane
because the Lakers sold a majority stake later
in 2025 that valued them at 10 billion. But that
6 .1 for the Celtics is the watershed moment.
Yeah. It forces the question, how? How do you
go from, you know, a startup in 1946 playing
in dusty, smoke -filled gyms. to a $6 billion
global asset. That is the mission today. We are
going to trace that line from the Red Auerbach
era through the tragedies of the 90s, the Big
Three resurgence, and then, of course, the modern
Jays era. That's quite right. But we have to
start at the beginning. 1946, the Basketball
Association of America forms. Boston gets a team.
And were they an instant hit? Far from it. They
were terrible. The team was founded by Walter
Brown. who ran the Boston Garden. They were losing
money, losing games. The real turning point didn't
happen until 1950, when they hired a guy named
Red Auerbach. The man who would eventually have
a cigar permanently glued to his hand? That's
the one. But you have to understand the context
of the NBA in the 50s. I mean, there were no
massive front offices, no analytics departments.
Right. Red Auerbach was the coach, the general
manager, the scout. He was practically the travel
agent. He was the entire operation. And he was,
let's say, a creative negotiator. I found a story
in the research that I actually didn't believe
it at first. It sounds like something from a
movie. Oh, I think I know where you're going
with this. It's 1956. The Celtics are desperate
to draft Bill Russell. Russell was the ultimate
prize. Coming out of the University of San Francisco,
he had two NCAA titles. Olympic gold medal. Everyone
knew he was an admitted genius. But the Celtics
don't have the number one pick. The Rochester
Royals do. So logic says the Royals take Russell.
Auerbach needs them to pass on him. So he can
trade for the number two pick and grab him. But
why on earth would Rochester pass on Bill Russell?
This is one of my favorite stories in sports
business history. It's amazing. Okay, so the
owner of the Celtics, Walter Brown, he had a
side hustle. He ran the Ice Capades. The traveling
ice skating show. which was huge entertainment
back then. I mean, no internet, no cable TV.
People went to the ice show. Exactly. And the
Rochester Royals owner, Les Harrison, was struggling
financially. He was having trouble filling his
arena. So Auerbach and Brown make him an offer.
They say, if you promise not to draft Bill Russell,
we will send the ice capades to Rochester for
a week -long run. Think about that. They didn't
trade a player. They didn't trade cash. They
traded a figure skating performance for the rights
to Bill Russell. It sounds like a front for something.
Here's some ice skaters. You give me the future
Hall of Famer. It was the Wild West. But it worked.
Rochester took Sehugo Green, a decent player,
but no Russell. And the Celtics traded for the
number two pick. They drafted Russell. And that
moment birthed the dynasty. Talk about return
on investment. But Auerbach wasn't just using
ice shows to build a team. He was also ignoring
the unspoken rules of the league regarding race.
He was. And this is a critical part of the legacy.
In 1950, Auerbach drafted Chuck Cooper. The first
black player ever selected by an NBA franchise.
And Red's philosophy was just brutally simple.
I don't give a damn if he's striped, plaid, or
polka dot. Boston takes the player who can win.
And that wasn't just talk. By 1964, the Celtics
did something that had never been done in U .S.
pro sports. They fielded the first all African
-American starting lineup. Bill Russell, Satch
Sanders, Casey Jones, Sam Jones and Willie Knowles.
Wow. Tom Heinsohn was injured and they just they
played a significant portion of the season that
way. And they didn't just break barriers. They
broke the will of every other team. The stats
from that era are just. They're laughable. They're
statistical anomalies. From 1957 to 1969, the
Celtics won 11 championships in 13 years. 11
in 13. That includes eight in a row. Eight consecutive
titles. In modern sports, winning two in a row
is considered a dynasty. They won eight. It just
breaks your brain when you compare it to today's
league. But Russell wasn't just the anchor on
the court. When Red finally retired from coaching
in 66, he made another historic move. He named
Bill Russell as his successor. Player coach.
Russell became the first black head coach in
any major U .S. professional sport. And he didn't
just hold a clipboard? No, he won two more titles
as the player coach in 68 and 69. So Russell
retires in 69. And usually when a dynasty like
that ends, the team just falls off a cliff for
20 years. But then the Celtics. They didn't.
Right. And this is a part of the history I feel
like people skip over. We always jump from Russell
straight to Larry Bird, but we need to talk about
the 70s. I'm glad you brought this up. The bridge
era is fascinating because it proved the Celtics
were a system, not just a vehicle for Bill Russell.
You had Dave Cowens and John Havlicek leading
the way. They won titles in 74 and 76. And 1976.
We have to stop there. The greatest game ever
played. Game five of the finals against the Phoenix
Suns. It is widely considered the wildest game
in NBA history. Triple overtime. Triple overtime.
The Suns hit a miracle shot at the buzzer of
the second overtime. Gar Hurd, the shot heard
around the world, to tie it. The fans in Boston
actually stormed the court thinking the game
was over. Before it was over. Yeah. The referees
had to clear the floor. It was total chaos. But
the Celtics pulled it out and won the title.
It just solidified that the winning culture wasn't
a fluke. But by the late 70s, the roster was
aging and the league itself was, you know, in
trouble. Big trouble. Ratings were down. Cocaine
was a major issue. The NBA needed the savior.
And they got two of them. 1979. Larry Bird arrives
in Boston. Magic Johnson arrives in Los Angeles.
And everything changes. This rivalry. It wasn't
just basketball, was it? It felt like a culture
war. Oh, it absolutely was. Yeah. You had the
Showtime Lakers, glitz, glamour, Hollywood, fast
breaks. And then you had the Celtics, blue collar,
physical, half court execution, black sneakers.
East Coast versus West Coast. It saved the NBA.
The viewership skyrocketed. whenever these two
teams played. And Red Auerbach, who is now the
general manager, decides he hasn't pulled off
enough heists yet. He needs to build a team around
Bird. So we get to the 1980 trade. The McHale
trade. This is another masterclass. The Celtics
held the number one overall pick. Most GMs would
just draft the best player, go home. Right. Auerbach
trades the number one pick to the Golden State
Warriors. In exchange, he gets Robert Parrish.
a center who was unhappy and underutilized in
Golden State, and the Warriors' number three
pick. So he trades down, gets a Hall of Fame
center in Parrish, and then with the third pick.
He drafts Kevin McHale. So in one afternoon,
he acquires two -thirds of the greatest front
court in the history of the game. Exactly. Bird,
McHale, and Parrish. The original big three,
they went on to win in 81 -84, and then the masterpiece
in 1986. That 86 team is the one people still
talk about. They had Bill Walton coming off the
bench. A healthy -ish Bill Walton. They went
40 -1 at home. They were arguably the greatest
passing team ever assembled. If you watch the
tape, the ball just never touches the floor.
It was beautiful. But then... Everything just
stops. And this is the part of the story that
turns into a Greek tragedy. We go from the highest
high in 86 to the lowest low imaginable. The
Len Bias tragedy. This is the moment that just
it broke the timeline. So they just won the championship.
And somehow they have the number two overall
pick in the draft. They draft Len Bias from Maryland.
He was supposed to be the guy to take the torch
from Larry Bird. He was a superstar. I can't
miss prospect. And less than 48 hours after being
drafted, he died of a cocaine overdose. It's
devastating on a human level, first and foremost,
but from a basketball perspective, it just left
this massive hole. It destroyed their future.
And then, as if that wasn't enough, in 1993,
their captain Reggie Lewis collapsed and later
died of a heart condition. So you lose your future
ace and your current captain in the span of seven
years. And that ushered in the dark ages. I grew
up in this era, and let me tell you, it was bleak.
The 90s Celtics were not the Celtics of lore.
They were irrelevant. They bottomed out 96 -97
with 15 wins and a franchise record 67 losses.
Yeah. They brought in Wick Pitino to save them,
thinking his college press system would work.
Spoiler, it did not. It was a complete disaster.
Dino famously ripped into the fans and press
yelling, Larry Bird is not walking through that
door. Kevin McHale is not walking through that
door. Which was true, but maybe not what the
fans wanted to hear while they were losing 60
games. It was a harsh reality check. The Celtics
mystique was dead. The team was just a bad basketball
team. So they needed a complete teardown. Enter
Danny Ainge. It's 2007. The team has been mediocre,
maybe even bad, for almost 20 years. Paul Pierce
is the captain, and he is miserable. He is. He's
playing with guys who wouldn't make a G League
roster today. And Ainge decides to push all his
chips into the middle of the table. The new big
three. Yep. He trades for Ray Allen. Then he
trades basically half the roster to get Kevin
Garnett from Minnesota. It was an instant super
team. They went from 24 wins to 66 wins in one
season. The biggest turnaround in league history.
And they capped it off by beating the Lakers
in 2008 for the 17th title. It was validation.
The franchise wasn't cursed. But here's the thing
about buying a super team. The window is small.
Garnett and Pierce were already in their 30s.
By 2013, they were running on fumes. And this
is where Danny Ainge pulls off what I think is
the greatest heist since the Ice Capades. The
Brooklyn trade. Oh, yeah. This is the defining
move of the modern era. In 2013, the Celtics
sent the aging Pierce and Garnett to the Brooklyn
Nets. The Nets had a new billionaire owner who
wanted to win a title right now and didn't. care
about the cost. So Brooklyn gets the big names.
What did Boston get? They got a handful of role
players, but the real assets were the draft picks.
2014, 2016, 2018, and a pick swap in 2017. But
here's the key detail people miss. The picks
were unprotected. OK, break that down for us.
Why does unprotected matter so much? Usually
when a team trades a future pick, they put protections
on it. They say if this pick ends up being number
one, two or three, we keep it and you get next
year's. It's insurance in case this team completely
collapses. Got it. Ainge convinced the Nets to
remove the insurance. He was essentially shorting
the Nets stock. He bet that by 2016, 2017, Garnett
and Pierce would be gone. The Nets would be terrible
and those picks would be gold. And he was right.
The Nets cratered and those draft picks turned
into. Jalen Brown in 2016 and Jason Tatum in
2017. The Jays, the foundation of the team that
just sold for over $6 billion. Incredible asset
managed it. They skipped the painful rebuilding
decade that usually follows a championship era.
They outsourced their tanking to Brooklyn. So
now we have the Jays. They grow together. They
make a finals run in 2022 but lose to Golden
State. And then finally, the 2023 -24 season.
A dominant march. 64 wins in the regular season.
They breezed through the playoffs. They beat
Dallas 4 -1 in the finals. Jalen Brown wins finals
MVP. And that's banner number 18, the tiebreaker
with the Lakers. It secured their spot at the
top of the mountain. But sports moves fast. We're
sitting here in 2026 looking back at the 24 -25
season where they won another division title
but got knocked out by the Knicks in the conference
semis. Right. Which brings us back to the ownership
change. The team is sold. And this is where I
want to get a little technical for a second.
We keep hearing about the second apron. It sounds
like kitchenware, but apparently it's terrifying
for billionaires. What is it? It's the new salary
cap rule that is, I mean, it's basically designed
to kill dynasties. If you spend over a certain
amount, the second apron. The league comes down
hard. How so? You lose your exceptions to sign
free agents. You can't trade your draft picks
seven years out. You can't aggregate salaries
and trades. It basically freezes your roster.
So in the 60s, Red could just keep paying Bill
Russell. In the 80s, they could pay Burr and
McHale. But now, if you pay Tatum and Brown's
Supermax contracts, you basically can't afford
anyone else without getting handcuffed by the
league? Precisely. And that's why the valuation
is so interesting. The new owners paid $6 .1
billion for a team that is incredibly expensive
to maintain. They're walking into a situation
where keeping this championship core together
for five or six years is mathematically punitive
in a way it never was before. So the question
is, was 2024 a standalone peak? Is the era of
the dynasty winning three or four rings in a
decade? Is that even possible anymore? I think
the definition of dynasty has to change. The
days of winning 11 and 13 years are gone. Impossible.
With the talent spread out and the financial
rules, maybe winning two in five years is the
new dynasty. Before we wrap up, though, I want
to touch on the one thing that money hasn't changed.
The vibe. The weird little traditions. The lore.
Yeah, we talked about the ice capades, but what
about Lucky the Leprechaun? Did you know Red
Auerbach's brother designed that logo? Zang Auerbach.
Yeah, he was a commercial artist. It's such a
mom -and -pop detail for a multi -billion dollar
brand. And the sneakers. For decades, if you
played for Boston, you wore black sneakers. Period.
Red hated white sneakers. He thought they looked
dirty and unprofessional. Even when Michael Jordan
was making colorful shoes famous. The Celtics
looked like they were wearing dress shoes. It
was psychological warfare. We are here to work.
We aren't here to look pretty. Totally. And the
parquet floor. It's iconic, but originally it
was just because of lumber scarcity after World
War II, right? Correct. They used scrap wood
to build the floor. And because it was scraps,
it had dead spots. The ball wouldn't bounce right
in certain areas. And I assume the Celtics knew
exactly where those spots were. Oh, absolutely.
You'd see opposing players dribble into a corner
and the ball would just die. Brett Auerbach loved
that. He claimed it was a myth, but he never
fixed the floor. It's that accumulation of history,
the floor, the cigars, the banners, that makes
that $6 .1 billion price tag make a little more
sense. You aren't just buying a basketball team.
You're buying a mythology. You're buying the
18 banners. You're buying the ghost of Red Auerbach.
And you're buying the expectation that Banner
19 is mandatory. That's the pressure the new
owners are walking into. Well, whether they win
another one next year or in another 16 years,
one thing is for sure, the price of admission
just went up. And hopefully they keep the black
sneakers. We can only hope. Thanks for diving
in with us. We'll catch you on the next one.