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The end began with a single conversation. It was spring 2007, and Al Jefferson was feeling optimistic. Though the Celtics had just limped through one of the worst seasons in franchise history, their 22-year-old big man had emerged, averaging career highs in points (16.0) and rebounds (11.0). A throwback big man who lived in the low post, Jefferson appeared to be on the verge of stardom. And he could smell the success ahead of him.

After Boston failed to qualify for the playoffs, Jefferson headed to Southern California to film a small part in a movie. While in Los Angeles, he spent some free time with Paul Pierce, the lone All-Star on his team. That day, Pierce dispensed some cryptic advice: You’re young and talented. Focus on trying to sign a big contract. You’re about to get paid.

"It kind of came out of nowhere," Jefferson said recently. "I was just sitting there thinking, ‘Paul knows something we don’t.’" The 13-year NBA veteran laughed — he still isn’t certain whether Pierce was clairvoyant or just clued in to the Celtics’ plans. Either way, The Truth proved worthy of his nickname. Jefferson soon did ink a big deal. But not in Boston.

With two moves that landed a pair of future Hall of Famers, Celtics president of basketball operations Danny Ainge famously managed to reshape his depleted roster into the league’s best. On draft night, he traded the rights to the fifth overall selection, guard Delonte West, forward Wally Szczerbiak, and a future second-round pick to the SuperSonics for Ray Allen and rookie forward Glen Davis. In July, Ainge sent five players and two first-round picks to the Timberwolves for Kevin Garnett. The key piece of the second swap was Jefferson, to whom Minnesota eventually gave a $65 million extension.

Even after watching his former club win a championship in June 2008, Jefferson understood that his old boss made the correct choice. "If I was Danny Ainge," he said, "I would’ve traded Al Jefferson for Kevin Garnett."

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Any smart executive would have.

"Who wouldn’t like to do what we were able to do in the summer of ’07?" Ainge said. "Every team wants to do that."

Yet over the last decade, no general manager has successfully replicated Ainge’s coup. After all, the Process of overhauling a bad team these days is like playing a progressive slot machine. Relying on green, young players; dumping big salaries; stockpiling first-round draft picks; and stashing prospects overseas may increase the jackpot, but the odds of winning the prize remain the same. To cash in, you need everything to break just right (and wrong).

Before the Celtics could be rebuilt, they had to survive a season in which they dealt with public criticism, a series of injuries, a historic losing streak, and Pierce’s profound frustration. "He was ready," then-teammate Tony Allen said, "to get up out of there."

It’s hard to imagine now, weeks after the crowd serenaded the 2008 Finals MVP during what very likely was his last appearance as a player at TD Garden, but during the 2006–07 season, Pierce felt he might have to leave Boston in order to win a title.

When I asked him about it in December, the 39-year-old, soon-to-be-retired Clippers player didn’t seem interested in revisiting that stretch of his career. He smiled, stonewalled my questions, slipped on a gray, Jordan Brand ski cap, and stepped out of the Los Angeles locker room into the concrete bowels of Staples Center. "Why do you want to talk about the Celtics?" he said before relenting to admit that he didn’t know if Ainge had had it in him to pull off two blockbuster trades.

"Truthfully, I wasn’t even sure," Pierce said. "It was my [ninth] year already, so it was make or break. He was either gonna do what he did or I was gonna be out of there."

After all, he added, "Those were the prime years for me. I’m a perennial All-Star and I want to win."

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Ainge’s construction project started well before summer 2007. First he had to rejigger the team’s roster, which he’d filled with bloated contracts. In January 2006, he shipped a package that included center Mark Blount and forward Ricky Davis to Minnesota for a 2009 first-round pick and three players, including Szczerbiak. Next he cobbled together three deals on draft night that June, exchanging big Raef LaFrentz (who was set to make $11.5 million the following season) and more for a 2008 second-round pick, center Theo Ratliff (whose $11.67 million-a-year contract was set to expire after 2007–08), guard Sebastian Telfair, and incoming rookies Leon Powe and Rajon Rondo.

All that tinkering left the Celtics with more flexibility but little else. "It was a miserable year," said then-coach Doc Rivers, who was hired in 2004. "But we knew going in that it would be tough. Me and Danny kind of adopted the plan that we were gonna play young guys."

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With Ohio State center Greg Oden and Texas forward Kevin Durant looming as the top prizes in the 2007 draft, the approach seemed shrewd. But it’s not as though Ainge and Rivers had any other choice. Only five players on the roster had more than three years of NBA experience. One, Ratliff, missed all but two games of the season due to a back injury. Another, Szczerbiak, was coming off of knee surgery. A third, Pierce, was stuck in NBA 101 when he should’ve been taking graduate-level courses.

"We would have shootarounds, and I’m teaching footwork and going over one play a hundred times," Rivers said. "I can’t imagine what Paul had to go through." By 2006, three years after he began running the Celtics, Ainge started to notice that Pierce’s patience was wearing thin. He recalled that at the time he and co-owners Wyc Grousbeck and Steve Pagliuca opened themselves up to Pierce in hopes of reaching him.

"It was the first time in my time there that Paul was really at his wit’s end and was very, very frustrated," Ainge said. "But I love how he handled it. He came in and we sat down — Wyc and Pags and myself — we talked to Paul. We shared with him our plan and our goal and he hung with us through that. It wasn’t easy."

On opening night in 2006, four days after Red Auerbach died at age 89, it was Pierce who grabbed the microphone at the packed Garden and gave an emotional tribute to the Celtics patriarch. Revered broadcaster Tommy Heinsohn, whose unconditional love of the team is even deeper than his hatred of NBA referees, approved of the speech.

"Pierce is reverent about the game itself, so he understood where he was at and what was involved," said Heinsohn, who played for and coached under Auerbach. "Even though he didn’t have an intimate relationship with Red, he understood his place in history."

After the ceremony, Pierce dropped 29 points on the Hornets. In a sign of things to come, the effort wasn’t enough. Boston missed three free throws in the final three minutes of the fourth quarter and fell 91–87. Less than a week later, Jefferson had an appendectomy and missed seven games.

The Celtics predictably struggled over the first two months of the season, but all was not lost. On December 9 against the Nets, Jefferson scored a then-career-high 29 points and Pierce hit a buzzer-beating jumper to give his team a 92–90 victory that snapped a five-game losing skid and started a five-game winning streak. Any optimism that short burst of success generated, however, faded fast.

On December 21, with Boston at 10–14 and inching toward .500, Pierce was diagnosed with a stress reaction in his left foot. He didn’t play for a month and a half, more than enough time for all hell to break loose.

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After their captain went down, the Celtics lost six of their next eight games. If there was a bright spot, it was Tony Allen. During that stretch, the third-year guard out of Oklahoma State averaged 18.8 points and 5.5 rebounds per game. "Tony had worked so hard to get that opportunity," Szczerbiak said. "He was playing so well."

Then, on January 10, Boston faced the Pacers at the Garden. Allen was having another big night — he notched 19 points and five steals in the game’s first 33 minutes — when he got the ball at the top of the key with just over three minutes left in the third quarter. After he gave a slight fake and drove to his left, Stephen Jackson reached out and was instantly called for a hand-checking foul. Instead of stopping, Allen took two more dribbles, sped past Indiana’s Sarunas Jasikevicius, and rose up for a one-handed dunk attempt that bounced off the back of the rim.

The whole thing looked blissfully innocuous until Allen landed. At that moment, all of his weight crashed down on his left leg. He collapsed on the baseline. As Rivers and Celtics trainer Ed Lacerte attended to Allen, he was in such pain that he started slapping the floor.

"It was heartbreaking," said Jefferson, Allen’s longtime friend. Jefferson still tells young players about the incident. "I use that as an example because once the whistle blows, I believe you should stop."

Lacerte and teammates Michael Olowokandi and Powe carried Allen off the court. The diagnosis was grim: Allen had an ACL tear and two mensicus tears in his left knee. "I just felt so bad for Tony," Ainge said. "He’s one of my favorite guys and always has been." Allen, who averaged a career-high 11.5 points in 33 games in 2006–07, didn’t return until the following season.

"I knew I was just gonna get back and be stronger than ever," said the now-35-year-old Allen, who never quite regained his scoring touch but has become one of the best defenders in the NBA. "Minor setback for major comeback. That’s all."

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The freak injury, Szczerbiak said, "summed up the snake-bit season for the Celtics." The already-struggling team crashed hard. From early January through mid-February, Boston lost 18 straight games, a franchise record. Pierce missed all but two of those. "When Paul went down with an injury, that made our life a little bit easier in that we were gonna play our younger guys," Ainge said.

Still, the Celtics didn’t exist in a vacuum. At a game in early February, a fan was spotted sitting 10 rows behind the Boston bench with a bag over his head. "One thing I did learn was that people don’t care about the plan," Rivers said. "They want you to win. And so I was taking a ton of heat. People were asking for me to get fired. People wanted to trade Paul Pierce."

The most vocal critic may have been Ringer CEO Bill Simmons, who, over the course of multiple columns, outlined the case against Rivers. "If Doc didn’t have a master plan last season, he certainly doesn’t have one this season," he wrote in November 2006. "He overstayed his welcome by about nine months, since the last time I wrote that he needed to go."

About midway through the losing streak, the coach remembered, Ainge approached him and said, "I love you. Hang in there."

Rivers was convinced that his boss thought that he was going to quit.

"But," Rivers added, "I never got that close to doing that."

For the players, the act of trying to stop the slide became downright Sisyphean. "You’re playing, you’re competing, and the games keep coming," said then–Celtics forward Ryan Gomes. "You have that thought in your mind, ‘Well, OK, we’ll get another crack at it tomorrow.’ After two games, after three games, after four games, then it’s starting to be a thing on SportsCenter. ‘Are the Celtics gonna keep losing?’ It just kept climbing and climbing. It does take a toll on you mentally."

The already Pierce-less Celtics didn’t catch many breaks, either. Late in the third quarter of a game against Shaquille O’Neal and the Heat — consecutive loss no. 16 — Szczerbiak attempted to block a shot, landed on Powe’s foot, and sprained his already-balky ankle. (After that defeat, the Associated Press reporter assigned to the game was so strapped for interesting notes that he mentioned this: "Boston Bruins defenseman Zdeno Chara, at 6-foot-9 the tallest player in the NHL, posed for pictures with O’Neal before the game.") Szczerbiak played only two more games that season before undergoing major ankle surgery.

What perhaps made it even more excruciating was that Boston wasn’t getting blown out. The Celtics dropped 12 of the 18 games by fewer than 10 points. During the streak, which ended with a 117–97 victory over the Bucks on February 14 (Pierce’s third game back from injury), they didn’t lose a game by more than 14.

"What you find out is every good bad team can stay in the game for three and a half quarters," Rivers said. "The bad bad teams are done in the first quarter. We were a good bad team." But not always. "There were a few games where, even as a coach, in the first quarter," Rivers admitted, "you’re like, ‘This is gonna be a long fucking night.’"

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Even through all the losing, the Celtics remained strangely compelling. After all, people wanted to see if they were terrible enough to land the first or second pick in the draft. In fact, in early 2007, Boston Globe columnist and feature writer Jackie MacMullan reported that the Celtics’ television ratings, attendance, and sponsorships had all increased. "It has been a disappointing season, but not a disappointing situation," Grousbeck told MacMullan, who’s penned dozens of definitive stories on the Ainge-era Celtics. In the same article, she also reported that after Boston executives showed video of Oden and Durant at an owners meeting, the NBA warned the Celtics against losing on purpose.

Which brings us to the T-word. Neither Ainge nor Rivers considered their plan to be tantamount to tanking. And even if they did, they never admitted it publicly. "One thing I don’t think people appreciate: Every night we thought we were gonna win," Rivers said.

On March 21, his claim was tested. That night, at home, the Celtics led the Bobcats 71–62 after three quarters. To begin the fourth, Rivers went with a lineup of Gomes, Powe, Rondo, Gerald Green, and Allan Ray, the last of whom was playing in Italy by the next fall. Less than 40 seconds later, Telfair came in for Rondo when he was called for his fifth foul. Halfway through the period, which Pierce missed after cutting the inside of his mouth, Charlotte took the lead. Only then did Brian Scalabrine, Jefferson, Rondo, and West reenter the game. It was too late; the Bobcats won 92–84.

Jefferson saw it as the coach’s way of challenging his young players. "You think you’re ready to play," he recalled Rivers telling the team, "so I let you play." Whatever Rivers was doing, he felt the need to defend it.

"I was not tanking the game," Rivers told reporters afterward. "I was not throwing the game or anything like that because I heard all those questions. Honestly, I got to the point early in the fourth quarter when I turned to my coaches and said, ‘We’re going to win or lose with this group.’"

By the time Rivers wisely inserted Rondo into the starting lineup in March, Pierce was hampered by both his foot injury and a sore left elbow. He was also growing more disillusioned by the day. He didn’t hold back publicly, either, at one point telling MacMullan, "It’s definitely another year gone by for me. It’s another year we don’t get into the postseason. It’s another year I don’t get recognized for the things I do. I’m the classic case of a great player on a bad team, and it stinks."

Pierce played his last game of 2006–07 on March 28, about three weeks before the season ended. Ainge knew by then that even though his team’s best player had signed a three-year contract extension in summer 2006, his time in Boston was running out. "Paul was with us," Ainge said. "At the same time, I knew that that had a life span. Just like Paul’s career has a life span."

Boston finished with a 24–58 record, the second worst in the NBA. (That was somehow nine games better than the worst Celtics team ever, the pre-Rick Pitino 1996–97 squad that went 15–67.) Still, the Celtics survived while also managing to put themselves in a uniquely advantageous position heading into the offseason.

"I thought we were gonna be a lot better," said Rivers, who signed a contract extension that May. "We were gonna have a [no.] 1 or [no.] 2 draft pick or we were gonna trade."

The makeover, however, was far beyond Rivers’s expectations.

"It was," he said, "euphoria."

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The 2007 NBA draft lottery was not the joyous event the team had hoped for. Entering into the annual drawing, held that year on May 22, Boston had a 38.7 percent chance of securing one of the first two picks. If the Celtics had been fortunate enough to be in the top two, they would’ve been in position to take Oden or Durant.

As deputy commissioner Adam Silver announced the draft order to Heinsohn and 13 other lottery team representatives stiffly sitting together on a TV set in Secaucus, New Jersey, that evening, many New Englanders were watching at home on tenterhooks. After the sixth pick went to the Bucks, Silver pulled a card out of envelope no. 5. On it was a leprechaun. On the ESPN telecast, the camera cut to Heinsohn, who looked like he wanted to rip the beige sport coat he was wearing to shreds.

For the Celtics, the fifth pick was what the percentages dictated was the worst possible outcome. Despite low odds, the Trail Blazers and Sonics nabbed the top spots. Ten years after missing out on Tim Duncan, Boston once again would fail to land a transformative superstar.

On draft night, Portland picked Oden and Seattle took Durant. Ainge, of course, made his trade for Ray Allen. Without knowing what was coming next, fans and media seemed perplexed. "On a list of improbable, no-one-of-sound-mind-and-sober-judgment-would-ever-do-such-a-thing acts," longtime Globe columnist Bob Ryan wrote on July 1, "trading the fifth pick of the NBA draft in a juicy year chock full of potential All-Stars for a 32-year-old shooting guard would have ranked at the bottom."

But Ainge wasn’t done. Sports Illustrated senior writer Ian Thomsen remembered running into him at an NBA summer league game in July 2007. "I sat with him up in the stands for a minute," said Thomsen, who’s covered the Celtics since their 1980s heyday. "He made it clear that he wasn’t done trading. His line was: ‘There’s a lot of quantity but not a lot of quality in the NBA.’ And so he was looking for quality."

On the last day of the month, Ainge and T-Wolves vice president of basketball operations Kevin McHale — fortuitously old friends from their playing days — agreed on a trade that sent Gomes, Green, Jefferson, Ratliff, Telfair, and two picks to Minnesota for Garnett. Less than a year later, the second Big Three lived up to its name, leading Boston to the 2008 championship before almost doing it again in 2010. The remade Celtics were a new kind of superteam: one built quickly.

In the decade since, other teams have tanked with hopes of landing the next Duncan or Durant. During his three years as GM of the 76ers, Sam Hinkie set his team up to fail so that he could hoard first-round picks. The problem with the approach, now both derisively and affectionately known as the Process, was that it led to loss after loss. "What are you teaching these young players when they come into the NBA?" Thomsen said. "You’re teaching them how to lose; you’re not teaching them how to win. They’re learning how to lose. That’s what they’re learning: to deal with failure, but not in a positive way." Philadelphia was so bad that in 2016 Hinkie was effectively demoted, and then he resigned.

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The Sixers have finally shown promise this season, but their architect is gone. Ainge could’ve met the same fate. Luckily for him, he didn’t have to start from scratch. Ainge had what Hinkie didn’t: Paul Pierce.

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An NBA megadeal is never good for all.

Jefferson always knew that Ainge was capable of making a big move. Before the 2006 draft, after the 6-foot-10 center–power forward’s second year in the NBA, Boston reportedly considered swapping him for Allen Iverson. That bothered Jefferson. "I did not want to be traded," he said. So, he added, "I stayed in Boston the whole summer, I worked my ass off, and I had a great season." When 2006–07 came to a close, he remembered saying to himself, "I still don’t want to be traded, but if I do get traded, at least I’m leaving on a good note."

In hindsight, he’s not terribly miffed by the fact that Ainge dealt him. "I understand the business," Jefferson said. "The veteran guys were telling me, ‘Man, you’re gonna play for a lot of different coaches, you’re gonna play for a lot of different teams. You can’t let that bother you. That’s the way the NBA works.’"

Ten years after the trade that saved the Celtics, Jefferson is used to upheaval. Now on the Pacers, he’s played for five franchises in 13 seasons. But part of him still wonders what his career might’ve looked like if he had stayed in Boston.

"I’ve told Paul Pierce, and I’ve told Doc Rivers, and I’ve told Danny Ainge this after I left," Jefferson said. "I really believe that if you would’ve kept me, Ray Allen, and Paul Pierce together — I’m not saying we would’ve won a championship that next year like they did — but I think we would’ve won one in the next two years."

Jefferson may have been right, but Ainge didn’t have the patience to wait and find out. That’s the thing about building an NBA team: When you have a chance at hitting the jackpot, you take it.

Alan Siegel
Alan covers a mix of movies, music, TV, and general nostalgia. He lives in Los Angeles and is currently writing a book about ‘The Simpsons’ that will be published in 2025.

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