Nov 30, 2017; Boston, MA, USA; President of basketball of operations Danny Ainge sits court side with writer Jackie McMullin prior to a game against the Philadelphia 76ers at TD Garden. Mandatory Credit: Bob DeChiara-USA TODAY Sports
The Danny Ainge era in Boston came to an inglorious end Wednesday when the team announced, a day after it was bounced from the playoffs, that he was stepping down. Brad Stevens, the Celtics coach for the past eight seasons, is leaving the sidelines to replace Ainge as president of basketball operations.
Celtics fans might feel a certain way about how things have unfolded in the franchise’s front office recently—the Kyrie Irving jokes are flying around and that situation certainly represented a low point. But Ainge’s legacy as an executive—after a successful stint as a player in Boston from 1981-89 where he won two titles and earned his only All-Star nod—was filled with more successes than failures. Most notably, he gets credit for building the 2007-08 team that won the organization’s first NBA title in 22 years.
Even if the Celtics were a mess this past season, grossly underachieving for a variety of reasons, Ainge leaves his post after 18 seasons with a reputation as one of the most respected roster builders and decisions makers in the NBA.
While Ainge will forever be lauded for acquiring Kevin Garnett and Ray Allen to complement Paul Pierce on that title team and fleecing Brooklyn in the deal that sent an aging KG and Pierce to the Nets for picks that eventually netted them their current cornerstones (Jayson Tatum and Jaylen Brown), he did not always land the players he coveted.
Every team has plenty of woculdas, couldas, shouldas and Ainge, with all his wheelings and dealings over the nearly two decades he ran the Celtics, whiffed on a number of top players. On his way out of Boston here are Ainge’s most notable trades he couldn’t consummate.
James Harden
Like almost every team in the NBA earlier this season, the Celtics made inquires to the Rockets about landing disgruntled James Harden when it became widely known he wanted out of Houston. Harden ended up in his preferred destination—Brooklyn where he teammed up with Kevin Durant and Kyrie Irving to form the scarriest offensive trio in league history—but Ainge attempted to acquire him for a significant haul. Unlike the Nets, he wasn’t willing to give up the hefty package the Rockets were demanding.
“The price was really high for us, and it was just something we didn’t want to do. I’m not sure there was anybody, even the people within our organization that respected him and wanted him more, but I think unanimously we decided it wasn’t the time for us and it wasn’t the price,” Ainge told New England sports radio program and podcast “Toucher and Rich” shortly after Harden was shipped to the Nets.
Kawhi Leonard
The Klaw as a Celtic? It could’ve happened in 2018 when Leonard was asking out of San Antonio. ESPN’s Adrian Wojnarowski mentioned it that June. Leonard, of course, was traded to Toronto and ended up leading the Raptors to their only NBA title two years ago. But Ainge reportedly had a shot at acquiring one of the premier two-way players in the Association. Sports Illustrated’s Chris Mannix revealed on The Crossover podcast back in 2019 there was “regret with some people in the Celtics organization about not pulling the trigger on a Kawhi Leonard deal.”
What did that deal look like? Mannix said the deal would’ve centered on Jaylen Brown and could’ve included Marcus Smart and/or other pieces.
Anthony Davis
Once Anthony Davis asked out of New Orleans three seasons ago, it didn’t take long for his wishlist of destinations to be revealed. Atop that wishlist was the Los Angeles Lakers. Not exactly a state secret around the NBA. The Celtics never were considered a serious landing spot for AD, especially after his father went on the record saying his son would never sign with the Celtics. But the idea of pairing AD with Kyrie Irving was way too intriguing for Ainge not to pursue.
It’s probably a good thing he didn’t. Rich Paul, Davis’s agent, told Sports Illustrated in a cover story that if the Celtics had managed to land him it wouldn’t have been a long marriage since AD was a year away from hitting free agency in the summer of 2019.
“If the Celtics traded for Anthony Davis, we would go there, and we would abide by our contractual obligations, and we would go into free agency in 2020,” Paul told the magazine. “I’ve stated that to them. In the event that he walks away…don’t blame Rich Paul.”
Chris Paul
A young CP3 could’ve been running point for the Celtics back in 2005 if Ainge had the temerity to trade Paul Pierce of the rights to the Point God. Who is the source of this information? Ainge himself. He revealed the incredibly enticing scenario on a Bill Simmons podcast back in 2013 when he told the media personality that he seriously thought about beginning a rebuilding process by packaging the Celtics legend for the player that will go down as one of the best point guards in NBA history.
Ray Allen also wrote about Paul potentially becoming a Celtic in his book, From the Outside: My Journey through Life and the Game I Love, that was released in 2018. He claims CP3 came close to joining the Celtics in 2011—Rajon Rondo would’ve been part of the package. Allen said then Celtics coach Doc Rivers didn’t want to trade Rondo for Paul because of his relationship with Monty Williams who was the coach of the Pelicans at the time
Paul George
The Boston Globe had the inside story on Ainge’s pursuit of a superstar and, according to the paper, the dealmaker spent a good portion of 2016 and 2017 trying to find a way to make PG a Celtic.
Adam Himmelsbach wrote that Ainge tried his best to pry George from the Pacers for four first-round picks at the 2017 trade deadline. Interestingly, one of the picks Ainge supposedly floated for George was the No. 1 selection in the NBA Draft. Ainge tried again to get PG ahead of the draft when the Globe says he offered three starters and a couple of first-rounders. The Pacers, of course, eventually shipped George to the Thunder a few weeks after the draft for Victor Oladipo and Domantas Sabonis.
Jimmy Butler
The current Miami Heat star has been rumored to be a Celtics target a few times in his career. The first came in 2016 when he was still with the Bulls and Boston was close to acquiring him during the summer. The Chicago Tribune reported:
The Bulls held advanced discussions with the Celtics centered on Butler and the No. 3 pick, with whom they would’ve selected Providence guard Kris Dunn, league sources said. Several proposals were exchanged, including one with Jae Crowder and the Celtics’ No. 3 and No. 16 picks, league sources said.
Ainge again looked into landing Butler in 2017, but ultimately passed when ESPN’s Zach Lowe reported the reason the Celtics didn’t pull the trigger was they had serious concerns over how Butler and Gordon Hayward, whom the Celtics had signed in free agency, “would mesh, both on the court and as personalities.”
Kevin Love
During his final few campaigns with the Timberwolves, Kevin Love was linked to a number of different destinations. We all know he ended up in Cleveland, and won a title with LeBron James and Kyrie Irving back in 2016 after the Cavs acquired him in exchange for Andrew Wiggins, the 2014 No. 1 overall pick, two seasons prior. But before Cleveland pulled the trigger during the summer of 2014, the Boston Globe reported Ainge was “convinced he can devise a package that would entice Minnesota Timberwolves president Flip Saunders to move” Love. Oh well.
Aaron Gordon
Ainge made a deal with the Magic—like a lot of other teams at March’s trade deadline—but he didn’t land the player most Celtics fans would’ve been hyped to welcome rather than Evan Fournier. Aaron Gordon was heavily linked to the Celtics when it became clear Orlando was ready to move the No. 4 pick in the who had soured on continuing to play losing basketball in Disney’s backyard. Gordon’s former teammate, Nikola Vucevic was also rumored to be an Ainge target, but the reports before that deadline made it seem like Ainge was way more intent on acquiring Gordon.