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Boston, November 4, 2018

You see Danny Ainge sitting at midcourt, headphones hugging his ears, ready to announce last Thursday’s Rockets-Lakers game with Kevin Harlan. You notice Houston’s DeMarcus Cousins strolling by him, ready to jump center in a nationally televised game. They probably won’t make eye contact, but you never know. You wait. They never look at each other.

“I would have said hello,” Ainge claims afterward. “He never looked at me. That’s fine. Look, it didn’t work out — if it had worked out, I wouldn’t be working for TNT, he wouldn’t be playing for Houston and Brad [Stevens] wouldn’t be coaching Duke.”

“That’s the risk you take when you make a big trade,” adds a still-shaken Wyc Grousbeck, the Celtics co-owner who approved the infamous Cousins trade in January 2017. “We definitely went all in, and it definitely didn’t work, and all you can do is move on. I never wanted to lose Danny or Brad, but that trade — I mean, it kind of broke both of them.”

The Boogie Trade will be remembered, probably forever, as the most demoralizing transaction in Celtics history. Blessed with a 50-win team, a cap-friendly roster, an outstanding coach, two choice Brooklyn lottery picks and an opportunity to own the 2020s, the Celtics rashly shoved their future into an NBA microwave. They talked themselves into Cousins, Sacramento’s undeniably gifted center who also had an undeniable penchant for landing in lotteries, melting down in games, and getting coaches fired. Ainge believed that Cousins needed only a stable organization and a winning foundation, that his superior talent would shine once Cousins found the right situation. Even then, deep down, Ainge knew it was a gamble that could land the Celtics their 18th title … or land Ainge back on TNT. He did it anyway.

“I knew it could be awful,” says Dan Shaughnessy, the longtime Boston Globe columnist. “I fully expected to turn him into a punch line and maybe even goad him into slugging me after a game. And that’s pretty much what happened. I still can’t totally see out of my left eye. But I never thought he’d bring down Danny and Brad.”

In retrospect, it was probably a bad omen that Boston’s inner circle was never aligned on Cousins. Stevens and president Rich Gotham believed, adamantly, that Cousins could undermine the team’s enviable chemistry and selflessness. The increasingly impatient Grousbeck still blanched at turning Boston’s war chest of picks and young assets into anything less than a sure thing. And Ainge kept steering everyone back to Cousins’s undeniable talent, as well as the nagging sense that Boston would never truly contend without having, as he calls it, “A Guy.”

“Look, we spent five years stockpiling enough assets to trade for an MVP candidate,” Ainge explains now. “In 2007, we needed Kevin [Garnett]. In 2017, we needed someone as talented as Kevin. We had to take a chance. You can’t win without A Guy.”

He’s right, actually. In the NBA’s past four decades, only the 2004 Pistons won without “A Guy” — every other champion had Kareem, Moses, Larry, Magic, Isiah, Jordan, Hakeem, Duncan, Shaq, Wade, Garnett, Kobe, Dirk, LeBron, Kawhi, Curry, and then last year, Curry and Durant. That’s 17 in all. Eleven were landed on draft day. Three signed as free agents. Three were acquired by mega-trade. We can’t remember every franchise that tanked a season hoping for a sure thing — Duncan, Durant, LeBron, Hakeem, Davis, whoever — because so many laughingstocks have tried. But getting seduced by a monster move that might land you in the Finals if it works out? That’s a shorter list, especially in the internet era, as many executives and owners find themselves paralyzed by a never-ending dissection of their moves. You can hide behind the quick-fix hope of those ping-pong balls on a floundering team. You can’t hide after a mega-deal — especially when it doesn’t work.

“I wanted them to trade for Cousins,” says an anonymous executive from an Eastern Conference team. “I thought he’d ruin their team. There’s only a couple of places he could have gone. He needs to be around an alpha, someone to keep his bullshit in check. Put him with LeBron or Westbrook or Popovich and he’s fine. The Celtics didn’t have anyone like that.”

Shortly after the trade, Cousins told the Boston Herald that “people never understood how bad it was in Sacramento, how messed up it was, how much it affected me. The team changed every year. Everything changed every year.” Read those words enough times and you want to believe them. But there was too much damage, too many losing seasons, too much dysfunction, too many scars. One former Boston teammate compared Cousins to a rescue dog that just couldn’t adjust to living in a normal home. “I actually like the guy; the whole thing just kind of snowballed.”

Boston fans bought into Cousins initially, bathing him in cheers and chanting “Booo-geee! Booo-geee!” during every foul line trip. Things soured after his infamous ESPN The Magazine interview, in which Cousins complained about Boston weather, made fun of Boston accents, called Boston drivers “crazy,” argued that Larry Bird was “overrated,” and vowed to show up at any Raiders-Patriots playoff game in a Raiders jersey because he was “silver and black for life.” In that same interview, he compared himself to Boston fans by saying, “They’re like me, they care, they really care. They actually care too much. They can be a little hot-headed about it. That’s like me. We just understand each other.”

But that’s the thing — they didn’t understand each other. Even with Cousins submitting big numbers (27 and 12 every night), the Celtics weren’t winning or jelling. (“We tried to get him too involved,” admits a somber Al Horford now, although Cousins’s negative impact on Boston’s once-stellar defense was probably a bigger issue.) After Cousins was thrown out of a February game against Cleveland for berating an official, Boston fans booed him and Cousins angrily gestured to the crowd. The following morning, WEEI’s Kirk & Callahan Show torched him. To their delight, they were surprised by how polarizing Cousins already was. Boston fans had been waiting to vent.

“We suddenly had our next four months of shows,” remembers cohost Kirk Minihane now. “People either defended him or hated him. There was no in between. There’s never been a Celtic quite like him. Then the Shaughnessy punch happened and … man … I mean … this was like crack for us.”

Should Cousins decking a 65-year-old sportswriter after an embarrassing home loss to Phoenix have been seen as a red flag? Unquestionably. But even after suspending Cousins for 10 games in March, the team continued to stand by its embattled big man. That unified front crumbled when Cousins’s former Kentucky teammate, John Wall, demanded a trade and Cousins openly lobbied for the Wizards star even though the trade deadline had passed. “You just can’t do that,” says Celtics announcer Brian Scalabrine. “The Celtics already had an All-Star point guard in Isaiah Thomas, someone who everyone really liked. How are you getting John Wall without giving up Isaiah?”

“Boogie was basically saying, ‘I wish I had a different point guard,’” says one of his former Boston teammates. “I get it, he loves John Wall, that’s his guy. But we all played hard and pulled for each other, and that killed us.”

After Charlotte bounced Boston in the first round and Sacramento shockingly won the lottery with Brooklyn’s pick — the crown jewel of Boston’s trade for Cousins — Celtics fans reacted as if Ainge had traded Fenway Park. Marcus Smart, Amir Johnson, two protected first-rounders, and the no. 1 overall pick in a loaded draft for a head-case center and a first-round exit? When news trickled out that Celtics legend Tommy Heinsohn had pushed the hardest for Cousins, gruffly telling his friend Ainge to stop overthinking the deal, that only made it worse. As the story went, Ainge asked if Red Auerbach would have gone after Cousins, and Heinsohn quickly fired back, “Red would’ve already gotten him.” Ainge pulled the trigger two hours later. Tommy Heinsohn is 84 years old.

“You can’t teach talent,” says ESPN’s Jalen Rose. “You can’t teach 6-foot-11, you can’t teach 30 and 15 every night, and you can’t teach pedigree. But you can ruin talent. You can give a player like Boogie two owners and six coaches and 11 point guards and four different front offices, and you can teach him bad habits, and you can teach him how to lose, and you can teach him how to hate a situation. Sacramento put Boogie in a position to fail for almost the entire time that Barack Obama was our president. Think about that. There was just too much damage.”

The Celtics ignored the signs, doubling down that June by dealing the popular Thomas, their 2018 Brooklyn pick, and a future protected pick from the Grizzlies for Washington’s franchise player. Suddenly the Team of the 2020s had turned into the Team of Now, built around Cousins, Wall, Horford, Jae Crowder, Avery Bradley, Jaylen Brown, Terry Rozier, and that’s about it. Cousins stunned the front office by rejecting a long-term extension, hoping to keep his 2018 free-agency options open. He should have just changed his nickname from “Boogie” to “Elephant in the Room.” Everyone said the right things, everyone smiled, everyone tried to seem happy, but when the team stumbled to a 9–10 start and fans started jeering Cousins at home games, you could see where this was headed.

“Except for Brad leaving,” says Celtics radio voice Sean Grande. “Nobody saw that one coming.”

When the popular Stevens abruptly resigned in January to become Mike Krzyzewski’s eventual successor at Duke, Boogie suddenly had a second nickname: “Coach Killer.” One “Boogie must go!” chant during a February home game enraged Cousins to the point that he no-showed the following game, leaving the Celtics no choice — they quickly traded him to Houston for 40 cents on the dollar (an unprotected first-rounder in 2020, expiring contracts, that’s it). The Celtics missed the playoffs and attempted to quickly rebuild around two 2018 lottery picks, neither of which cracked the top five. Meanwhile, Sacramento’s prize from the Cousins trade, stud point guard Markelle Fultz, became the league’s Rookie of the Year. The damage was complete.

“I don’t have much to say about it,” says Stevens now. “We took a big swing and it didn’t work. I’m looking forward and I wish the Celtics the best.”

“That’s the real tragedy here,” says Bob Ryan, the esteemed Boston Globe columnist who’s been following the team since the 1960s. “The Celtics so desperately wanted a franchise player, and the whole time, they had one — they had Brad. They just needed to be patient, let Golden State own this decade, then build for the next decade with Brad and all those assets. And they just couldn’t wait. They couldn’t wait.”

NBA history is littered with teams that took big swings that didn’t work. New Orleans spent two first-round picks to acquire Gail Goodrich; one of them became Magic Johnson. Phoenix and New York both swung and missed on Stephon Marbury. The Lakers blew it with Dwight Howard in the same trade that Philly blew it with Andrew Bynum. Dallas never should have traded Jason Kidd. Philly never should have traded Charles Barkley. You could go on for days. And yet, it’s hard to remember one transaction flipping the destiny of a perennial contender faster than that Cousins trade.

Cousins refused to comment for this story other than to reiterate that he was glad he punched Shaughnessy, even after settling their multimillion-dollar lawsuit. Surprisingly, Ainge insists that he “would totally make that trade again. Golden State just won three titles in four years. They have two of the best three guys in the league. They’re a historically great team. We couldn’t beat them without taking a swing.”

As Ainge speaks, Houston’s arena is still clearing out around him after a blowout victory for the Rockets. Cousins scored 29 points, grabbed 16 rebounds, and seemed happy playing with James Harden and Eric Gordon. For now, anyway.

“You saw it tonight,” Ainge says, fiddling with his TNT headset. “The guy is legitimately talented. It was the right gamble for us. It just didn’t work.”

And then some.