WEBVTT

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Okay, I want you to picture the color green.

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And I don't just mean the color of money. Though,

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uh, spoiler alert. We are definitely going to

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talk about a boatload of cash today. A literal

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boatload. I'm talking about that specific Kelly

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Green. I'm talking about, you know, that leprechaun

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lucky and clouds of cigar smoke and that bizarre

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floor that makes the ball bounce sideways. You're

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talking about the Boston Celtics. We are unpacking

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the legacy of the Boston Celtics today. And it

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really is the story of the NBA in a lot of ways.

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Yeah. I mean, if you just took the Celtics out

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of the history books, the league would look completely

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different. Oh, completely. talking about a franchise

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that as of 2024, finally broke that tie with

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the Lakers. Stood alone with 18 championships.

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They've got more wins than any other team in

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history. It's a resume that, frankly, reads like

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fiction. It does. But here's the thing that really

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grabbed me and why we're doing this deep dive

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right now. It's not just the trophies. It's the

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valuation. We're recording this looking back

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at May of 2025, which feels like just yesterday,

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when the team was sold to William Chisholm and

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his private equity group. For 6 .1. billion dollars

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6 .1 billion with a b I tried to visualize that

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amount of money earlier today and I just. I got

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a headache. It's a staggering number. And at

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the moment the Inc. tried, it was the highest

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price ever paid for a North American sports franchise.

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Right. Now, we know the market is just insane

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because the Lakers sold a majority stake later

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in 2025 that valued them at 10 billion. But that

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6 .1 for the Celtics is the watershed moment.

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Yeah. It forces the question, how? How do you

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go from, you know, a startup in 1946 playing

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in dusty, smoke -filled gyms. to a $6 billion

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global asset. That is the mission today. We are

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going to trace that line from the Red Auerbach

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era through the tragedies of the 90s, the Big

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Three resurgence, and then, of course, the modern

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Jays era. That's quite right. But we have to

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start at the beginning. 1946, the Basketball

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Association of America forms. Boston gets a team.

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And were they an instant hit? Far from it. They

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were terrible. The team was founded by Walter

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Brown. who ran the Boston Garden. They were losing

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money, losing games. The real turning point didn't

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happen until 1950, when they hired a guy named

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Red Auerbach. The man who would eventually have

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a cigar permanently glued to his hand? That's

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the one. But you have to understand the context

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of the NBA in the 50s. I mean, there were no

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massive front offices, no analytics departments.

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Right. Red Auerbach was the coach, the general

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manager, the scout. He was practically the travel

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agent. He was the entire operation. And he was,

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let's say, a creative negotiator. I found a story

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in the research that I actually didn't believe

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it at first. It sounds like something from a

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movie. Oh, I think I know where you're going

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with this. It's 1956. The Celtics are desperate

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to draft Bill Russell. Russell was the ultimate

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prize. Coming out of the University of San Francisco,

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he had two NCAA titles. Olympic gold medal. Everyone

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knew he was an admitted genius. But the Celtics

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don't have the number one pick. The Rochester

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Royals do. So logic says the Royals take Russell.

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Auerbach needs them to pass on him. So he can

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trade for the number two pick and grab him. But

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why on earth would Rochester pass on Bill Russell?

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This is one of my favorite stories in sports

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business history. It's amazing. Okay, so the

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owner of the Celtics, Walter Brown, he had a

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side hustle. He ran the Ice Capades. The traveling

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ice skating show. which was huge entertainment

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back then. I mean, no internet, no cable TV.

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People went to the ice show. Exactly. And the

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Rochester Royals owner, Les Harrison, was struggling

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financially. He was having trouble filling his

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arena. So Auerbach and Brown make him an offer.

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They say, if you promise not to draft Bill Russell,

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we will send the ice capades to Rochester for

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a week -long run. Think about that. They didn't

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trade a player. They didn't trade cash. They

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traded a figure skating performance for the rights

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to Bill Russell. It sounds like a front for something.

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Here's some ice skaters. You give me the future

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Hall of Famer. It was the Wild West. But it worked.

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Rochester took Sehugo Green, a decent player,

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but no Russell. And the Celtics traded for the

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number two pick. They drafted Russell. And that

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moment birthed the dynasty. Talk about return

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on investment. But Auerbach wasn't just using

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ice shows to build a team. He was also ignoring

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the unspoken rules of the league regarding race.

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He was. And this is a critical part of the legacy.

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In 1950, Auerbach drafted Chuck Cooper. The first

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black player ever selected by an NBA franchise.

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And Red's philosophy was just brutally simple.

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I don't give a damn if he's striped, plaid, or

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polka dot. Boston takes the player who can win.

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And that wasn't just talk. By 1964, the Celtics

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did something that had never been done in U .S.

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pro sports. They fielded the first all African

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-American starting lineup. Bill Russell, Satch

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Sanders, Casey Jones, Sam Jones and Willie Knowles.

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Wow. Tom Heinsohn was injured and they just they

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played a significant portion of the season that

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way. And they didn't just break barriers. They

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broke the will of every other team. The stats

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from that era are just. They're laughable. They're

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statistical anomalies. From 1957 to 1969, the

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Celtics won 11 championships in 13 years. 11

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in 13. That includes eight in a row. Eight consecutive

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titles. In modern sports, winning two in a row

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is considered a dynasty. They won eight. It just

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breaks your brain when you compare it to today's

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league. But Russell wasn't just the anchor on

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the court. When Red finally retired from coaching

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in 66, he made another historic move. He named

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Bill Russell as his successor. Player coach.

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Russell became the first black head coach in

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any major U .S. professional sport. And he didn't

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just hold a clipboard? No, he won two more titles

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as the player coach in 68 and 69. So Russell

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retires in 69. And usually when a dynasty like

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that ends, the team just falls off a cliff for

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20 years. But then the Celtics. They didn't.

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Right. And this is a part of the history I feel

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like people skip over. We always jump from Russell

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straight to Larry Bird, but we need to talk about

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the 70s. I'm glad you brought this up. The bridge

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era is fascinating because it proved the Celtics

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were a system, not just a vehicle for Bill Russell.

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You had Dave Cowens and John Havlicek leading

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the way. They won titles in 74 and 76. And 1976.

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We have to stop there. The greatest game ever

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played. Game five of the finals against the Phoenix

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Suns. It is widely considered the wildest game

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in NBA history. Triple overtime. Triple overtime.

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The Suns hit a miracle shot at the buzzer of

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the second overtime. Gar Hurd, the shot heard

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around the world, to tie it. The fans in Boston

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actually stormed the court thinking the game

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was over. Before it was over. Yeah. The referees

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had to clear the floor. It was total chaos. But

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the Celtics pulled it out and won the title.

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It just solidified that the winning culture wasn't

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a fluke. But by the late 70s, the roster was

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aging and the league itself was, you know, in

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trouble. Big trouble. Ratings were down. Cocaine

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was a major issue. The NBA needed the savior.

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And they got two of them. 1979. Larry Bird arrives

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in Boston. Magic Johnson arrives in Los Angeles.

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And everything changes. This rivalry. It wasn't

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just basketball, was it? It felt like a culture

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war. Oh, it absolutely was. Yeah. You had the

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Showtime Lakers, glitz, glamour, Hollywood, fast

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breaks. And then you had the Celtics, blue collar,

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physical, half court execution, black sneakers.

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East Coast versus West Coast. It saved the NBA.

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The viewership skyrocketed. whenever these two

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teams played. And Red Auerbach, who is now the

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general manager, decides he hasn't pulled off

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enough heists yet. He needs to build a team around

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Bird. So we get to the 1980 trade. The McHale

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trade. This is another masterclass. The Celtics

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held the number one overall pick. Most GMs would

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just draft the best player, go home. Right. Auerbach

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trades the number one pick to the Golden State

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Warriors. In exchange, he gets Robert Parrish.

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a center who was unhappy and underutilized in

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Golden State, and the Warriors' number three

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pick. So he trades down, gets a Hall of Fame

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center in Parrish, and then with the third pick.

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He drafts Kevin McHale. So in one afternoon,

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he acquires two -thirds of the greatest front

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court in the history of the game. Exactly. Bird,

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McHale, and Parrish. The original big three,

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they went on to win in 81 -84, and then the masterpiece

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in 1986. That 86 team is the one people still

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talk about. They had Bill Walton coming off the

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bench. A healthy -ish Bill Walton. They went

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40 -1 at home. They were arguably the greatest

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passing team ever assembled. If you watch the

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tape, the ball just never touches the floor.

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It was beautiful. But then... Everything just

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stops. And this is the part of the story that

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turns into a Greek tragedy. We go from the highest

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high in 86 to the lowest low imaginable. The

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Len Bias tragedy. This is the moment that just

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it broke the timeline. So they just won the championship.

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And somehow they have the number two overall

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pick in the draft. They draft Len Bias from Maryland.

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He was supposed to be the guy to take the torch

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from Larry Bird. He was a superstar. I can't

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miss prospect. And less than 48 hours after being

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drafted, he died of a cocaine overdose. It's

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devastating on a human level, first and foremost,

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but from a basketball perspective, it just left

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this massive hole. It destroyed their future.

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And then, as if that wasn't enough, in 1993,

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their captain Reggie Lewis collapsed and later

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died of a heart condition. So you lose your future

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ace and your current captain in the span of seven

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years. And that ushered in the dark ages. I grew

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up in this era, and let me tell you, it was bleak.

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The 90s Celtics were not the Celtics of lore.

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They were irrelevant. They bottomed out 96 -97

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with 15 wins and a franchise record 67 losses.

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Yeah. They brought in Wick Pitino to save them,

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thinking his college press system would work.

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Spoiler, it did not. It was a complete disaster.

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Dino famously ripped into the fans and press

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yelling, Larry Bird is not walking through that

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door. Kevin McHale is not walking through that

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door. Which was true, but maybe not what the

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fans wanted to hear while they were losing 60

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games. It was a harsh reality check. The Celtics

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mystique was dead. The team was just a bad basketball

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team. So they needed a complete teardown. Enter

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Danny Ainge. It's 2007. The team has been mediocre,

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maybe even bad, for almost 20 years. Paul Pierce

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is the captain, and he is miserable. He is. He's

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playing with guys who wouldn't make a G League

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roster today. And Ainge decides to push all his

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chips into the middle of the table. The new big

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three. Yep. He trades for Ray Allen. Then he

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trades basically half the roster to get Kevin

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Garnett from Minnesota. It was an instant super

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team. They went from 24 wins to 66 wins in one

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season. The biggest turnaround in league history.

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And they capped it off by beating the Lakers

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in 2008 for the 17th title. It was validation.

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The franchise wasn't cursed. But here's the thing

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about buying a super team. The window is small.

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Garnett and Pierce were already in their 30s.

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By 2013, they were running on fumes. And this

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is where Danny Ainge pulls off what I think is

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the greatest heist since the Ice Capades. The

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Brooklyn trade. Oh, yeah. This is the defining

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move of the modern era. In 2013, the Celtics

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sent the aging Pierce and Garnett to the Brooklyn

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Nets. The Nets had a new billionaire owner who

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wanted to win a title right now and didn't. care

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about the cost. So Brooklyn gets the big names.

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What did Boston get? They got a handful of role

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players, but the real assets were the draft picks.

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2014, 2016, 2018, and a pick swap in 2017. But

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here's the key detail people miss. The picks

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were unprotected. OK, break that down for us.

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Why does unprotected matter so much? Usually

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when a team trades a future pick, they put protections

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on it. They say if this pick ends up being number

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one, two or three, we keep it and you get next

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year's. It's insurance in case this team completely

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collapses. Got it. Ainge convinced the Nets to

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remove the insurance. He was essentially shorting

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the Nets stock. He bet that by 2016, 2017, Garnett

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and Pierce would be gone. The Nets would be terrible

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and those picks would be gold. And he was right.

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The Nets cratered and those draft picks turned

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into. Jalen Brown in 2016 and Jason Tatum in

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2017. The Jays, the foundation of the team that

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just sold for over $6 billion. Incredible asset

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managed it. They skipped the painful rebuilding

00:12:10.250 --> 00:12:12.610
decade that usually follows a championship era.

00:12:12.710 --> 00:12:15.110
They outsourced their tanking to Brooklyn. So

00:12:15.110 --> 00:12:17.230
now we have the Jays. They grow together. They

00:12:17.230 --> 00:12:19.330
make a finals run in 2022 but lose to Golden

00:12:19.330 --> 00:12:23.330
State. And then finally, the 2023 -24 season.

00:12:23.450 --> 00:12:26.409
A dominant march. 64 wins in the regular season.

00:12:26.610 --> 00:12:29.129
They breezed through the playoffs. They beat

00:12:29.129 --> 00:12:32.730
Dallas 4 -1 in the finals. Jalen Brown wins finals

00:12:32.730 --> 00:12:35.610
MVP. And that's banner number 18, the tiebreaker

00:12:35.610 --> 00:12:37.769
with the Lakers. It secured their spot at the

00:12:37.769 --> 00:12:40.809
top of the mountain. But sports moves fast. We're

00:12:40.809 --> 00:12:43.590
sitting here in 2026 looking back at the 24 -25

00:12:43.590 --> 00:12:46.029
season where they won another division title

00:12:46.029 --> 00:12:48.509
but got knocked out by the Knicks in the conference

00:12:48.509 --> 00:12:51.289
semis. Right. Which brings us back to the ownership

00:12:51.289 --> 00:12:54.370
change. The team is sold. And this is where I

00:12:54.370 --> 00:12:55.730
want to get a little technical for a second.

00:12:55.830 --> 00:12:58.529
We keep hearing about the second apron. It sounds

00:12:58.529 --> 00:13:00.350
like kitchenware, but apparently it's terrifying

00:13:00.350 --> 00:13:03.009
for billionaires. What is it? It's the new salary

00:13:03.009 --> 00:13:05.370
cap rule that is, I mean, it's basically designed

00:13:05.370 --> 00:13:07.889
to kill dynasties. If you spend over a certain

00:13:07.889 --> 00:13:10.590
amount, the second apron. The league comes down

00:13:10.590 --> 00:13:13.210
hard. How so? You lose your exceptions to sign

00:13:13.210 --> 00:13:15.149
free agents. You can't trade your draft picks

00:13:15.149 --> 00:13:17.330
seven years out. You can't aggregate salaries

00:13:17.330 --> 00:13:19.629
and trades. It basically freezes your roster.

00:13:19.889 --> 00:13:22.230
So in the 60s, Red could just keep paying Bill

00:13:22.230 --> 00:13:24.429
Russell. In the 80s, they could pay Burr and

00:13:24.429 --> 00:13:27.389
McHale. But now, if you pay Tatum and Brown's

00:13:27.389 --> 00:13:29.450
Supermax contracts, you basically can't afford

00:13:29.450 --> 00:13:31.190
anyone else without getting handcuffed by the

00:13:31.190 --> 00:13:33.940
league? Precisely. And that's why the valuation

00:13:33.940 --> 00:13:37.159
is so interesting. The new owners paid $6 .1

00:13:37.159 --> 00:13:40.059
billion for a team that is incredibly expensive

00:13:40.059 --> 00:13:42.779
to maintain. They're walking into a situation

00:13:42.779 --> 00:13:44.759
where keeping this championship core together

00:13:44.759 --> 00:13:48.879
for five or six years is mathematically punitive

00:13:48.879 --> 00:13:51.259
in a way it never was before. So the question

00:13:51.259 --> 00:13:55.379
is, was 2024 a standalone peak? Is the era of

00:13:55.379 --> 00:13:57.620
the dynasty winning three or four rings in a

00:13:57.620 --> 00:14:00.360
decade? Is that even possible anymore? I think

00:14:00.360 --> 00:14:02.620
the definition of dynasty has to change. The

00:14:02.620 --> 00:14:05.440
days of winning 11 and 13 years are gone. Impossible.

00:14:05.679 --> 00:14:07.200
With the talent spread out and the financial

00:14:07.200 --> 00:14:09.659
rules, maybe winning two in five years is the

00:14:09.659 --> 00:14:11.720
new dynasty. Before we wrap up, though, I want

00:14:11.720 --> 00:14:13.639
to touch on the one thing that money hasn't changed.

00:14:14.029 --> 00:14:16.529
The vibe. The weird little traditions. The lore.

00:14:16.730 --> 00:14:18.690
Yeah, we talked about the ice capades, but what

00:14:18.690 --> 00:14:20.590
about Lucky the Leprechaun? Did you know Red

00:14:20.590 --> 00:14:23.610
Auerbach's brother designed that logo? Zang Auerbach.

00:14:23.850 --> 00:14:26.309
Yeah, he was a commercial artist. It's such a

00:14:26.309 --> 00:14:29.210
mom -and -pop detail for a multi -billion dollar

00:14:29.210 --> 00:14:32.649
brand. And the sneakers. For decades, if you

00:14:32.649 --> 00:14:35.549
played for Boston, you wore black sneakers. Period.

00:14:35.830 --> 00:14:37.950
Red hated white sneakers. He thought they looked

00:14:37.950 --> 00:14:40.610
dirty and unprofessional. Even when Michael Jordan

00:14:40.610 --> 00:14:44.200
was making colorful shoes famous. The Celtics

00:14:44.200 --> 00:14:46.460
looked like they were wearing dress shoes. It

00:14:46.460 --> 00:14:49.360
was psychological warfare. We are here to work.

00:14:49.460 --> 00:14:51.950
We aren't here to look pretty. Totally. And the

00:14:51.950 --> 00:14:54.889
parquet floor. It's iconic, but originally it

00:14:54.889 --> 00:14:56.870
was just because of lumber scarcity after World

00:14:56.870 --> 00:14:59.230
War II, right? Correct. They used scrap wood

00:14:59.230 --> 00:15:01.970
to build the floor. And because it was scraps,

00:15:02.210 --> 00:15:04.950
it had dead spots. The ball wouldn't bounce right

00:15:04.950 --> 00:15:07.070
in certain areas. And I assume the Celtics knew

00:15:07.070 --> 00:15:08.750
exactly where those spots were. Oh, absolutely.

00:15:09.029 --> 00:15:11.370
You'd see opposing players dribble into a corner

00:15:11.370 --> 00:15:13.850
and the ball would just die. Brett Auerbach loved

00:15:13.850 --> 00:15:16.049
that. He claimed it was a myth, but he never

00:15:16.049 --> 00:15:18.440
fixed the floor. It's that accumulation of history,

00:15:18.700 --> 00:15:21.620
the floor, the cigars, the banners, that makes

00:15:21.620 --> 00:15:24.440
that $6 .1 billion price tag make a little more

00:15:24.440 --> 00:15:26.700
sense. You aren't just buying a basketball team.

00:15:26.860 --> 00:15:29.399
You're buying a mythology. You're buying the

00:15:29.399 --> 00:15:32.299
18 banners. You're buying the ghost of Red Auerbach.

00:15:32.500 --> 00:15:34.899
And you're buying the expectation that Banner

00:15:34.899 --> 00:15:38.059
19 is mandatory. That's the pressure the new

00:15:38.059 --> 00:15:41.059
owners are walking into. Well, whether they win

00:15:41.059 --> 00:15:43.519
another one next year or in another 16 years,

00:15:43.639 --> 00:15:46.000
one thing is for sure, the price of admission

00:15:46.000 --> 00:15:48.340
just went up. And hopefully they keep the black

00:15:48.340 --> 00:15:50.980
sneakers. We can only hope. Thanks for diving

00:15:50.980 --> 00:15:52.700
in with us. We'll catch you on the next one.
