Celtics general manager Danny Ainge may be the NBA’s premier trade architect. In 2007, Ainge turned one of the league’s worst teams into a champion contender in a few days when he pulled off a pair of trades to bring Kevin Garnett and Ray Allen to Boston, leading to a 2008 title and a half-decade of deep playoff runs. When that superteam ran out of juice, Ainge ensured another decade of Celtics success by flipping Garnett and Paul Pierce to the star-hungry Nets, turning the tapped-out superstars into four future first-round picks in what would become one of the most lopsided trades in NBA history. As the Nets floundered, one of those picks turned out to be the no. 1 pick in the 2017 NBA draft—which Ainge smartly flipped again, correctly guessing that consensus top pick Markelle Fultz wouldn’t live up to the hype and instead drafting the team’s new franchise player, Jayson Tatum, at no. 3. Shortly after that, Ainge managed to turn the brief window when Isaiah Thomas looked like a top-tier NBA player into a couple of years of prime Kyrie Irving. All things told, the Celtics have been a relevant squad for almost 15 consecutive years on the strength of Ainge’s trading capabilities.
It’s almost a necessity that the Celtics take big swings on the trade market. This era of the NBA has been defined almost entirely by free agency, and the league’s premier players have completely ignored Boston as an option. While other franchises have built superteams with multiple All-NBA free agents, the Celtics’ biggest signings have been Gordon Hayward and Kemba Walker. If the Celtics want to get top-tier players, they have to trade for them.
And since getting Irving, it’s been awfully quiet. Many assumed that the Celtics would pull off something big at this year’s trade deadline, as the team has underperformed and struggled to reach .500. Plus, they have a record-setting trade exception allowing them to blow past the NBA salary cap if they bring in expensive players via trade. Instead, Boston’s trade deadline haul was minor: The Celtics added Evan Fournier, Moritz Wagner, and Luke Kornet. Was Ainge asleep at the wheel? No—after the deadline, it was reported that the Celtics “were a finalist” for All-Star Nikola Vucevic, and that they had also been in the running to acquire his former Magic teammate Aaron Gordon. The two best players dealt at the deadline, and the Celtics almost got them both—but just couldn’t pull it off.
Over the past years, this has become a trend. Every time an All-Star does get dealt, the trade is quickly followed by reports that the Celtics almost got that player. The Celtics keep getting nothing but rumors, with the whiffs teasing fans who daydream about the Celtics having a much better team. It’s possible all these reports are true—after all, Ainge does have a history of taking big swings on the trade market. But it feels suspiciously like somebody within the Celtics front office really wants the world to know that even when the team doesn’t land a superstar, it was only inches away from pulling off the deal. So who could the leaker be? Well, it could be anybody who simply wants the world to know how great the Celtics GM is—maybe even a former Celtics player whose game had Uncanny Range. This is the story of Almost Ainge, the executive who almost dealt for every superstar in the NBA.
Below, we’ve assembled a roster of the best players the Celtics are rumored to have almost acquired—the Almost Ainge All-Stars.
(A few logistical notes: Every player below has been rumored to have almost been sent to the Celtics in a trade. A simple rumor that the team is interested in a player doesn’t cut it. We’re also not including free agency—although it should be noted the Celtics were also a finalist for Kevin Durant in 2019. And finally, we’re not setting a starting lineup. It’s up to you to imagine how Brad Stevens would deploy this cast of All-Stars.)
In January, the Nets cemented their new Big Three by trading for the NBA’s back-to-back-to-back scoring champ, making themselves instant favorites to win the title and ensuring they would remain contenders for years to come. But don’t worry—the Celtics nearly got Harden, too. Ainge confirmed that the Celtics had “numerous talks” with the Rockets to potentially add the Beard, but that “the price was really high for us.” Brian Robb of Boston Sports Journal reported that price: Jaylen Brown, Marcus Smart, and “draft compensation”—probably multiple first-rounders, considering the Nets ultimately gave up four first-round picks for Harden.
It does sound like a pretty high price—but the price of not making the trade is that the Celtics won’t be the best team in their own division for years to come.
In 2013, on our own Bill Simmons’s podcast, Ainge relayed a story of how in 2005 he nearly made a Paul Swap—dealing Pierce for Chris. It’s atypical of the usual Almost Ainge entry, most of which are anonymous reports days after a trade wasn’t made, while this was a comment Ainge himself made years after the fact.
When Butler was in his final days with the Bulls, the Celtics were repeatedly linked in trade rumors. After the 2016 NBA draft, K.C. Johnson, then of the Chicago Tribune, reported that the Celtics had been in “advanced discussions” to land Butler. The deal reportedly featured the third pick (which the Bulls wanted to use on Kris Dunn), the 16th pick, and Jae Crowder—but Johnson wrote that “the Celtics have a reputation of trying to win trades and kept changing the terms.” (Lending credence to Johnson’s report: the fact that the Bulls targeted Dunn in the 2017 package that eventually sent Butler to Minnesota.)
After not trading for Butler, Celtics owner Wyc Grousbeck said that the trades offered to the team on draft night were “a collection of rip-off attempts and we laughed at them.” (The Celtics would continue to be linked to Butler through the 2017 trade deadline, when the Celtics were again near a trade but, according to NBA.com reporter David Aldridge, refused to include Jae Crowder. That summer, ESPN’s Zach Lowe reported that the Celtics didn’t end up trading for Butler because the team “had some concerns over how [Gordon] Hayward and Butler would mesh, both on court and as personalities.”
The Celtics may have laughed at the trade offers that would have brought Butler to the Celtics, but I think it’s clear that the funniest thing here is that the Celtics may have vetoed a trade for a future All-NBA guy because they were worried he wouldn’t be friends with Gordon Hayward.
In 2019, Leonard made one of the greatest playoff runs of all time, leading the Raptors, who had traded for him the previous summer, to their first title. He spent only one year in Toronto, but it was worth it for the Raptors, as Leonard may have been the most successful superstar rental in NBA history. But there could have been a different team that year that benefited from Kawhi’s services: Chris Mannix of Sports Illustrated reported that Boston “could have made a deal” for Leonard featuring Jaylen Brown and potentially Marcus Smart. Mannix reported that the Spurs preferred the Celtics’ trade package to the Raptors’, and that “there is some regret with some people in the Celtics’ organization about not pulling the trigger.”
It’s worth noting that Mannix made this report literally while the Raptors were playing the NBA Finals and beating the seemingly unstoppable Warriors. You can really see the mental image of the Celtics front office watching the Raptors roll to a championship and thinking, “people need to know that this could have been us!”
As with Butler, the Celtics spent most of 2016 and 2017 chasing George. Adam Himmelsbach of The Boston Globe wrote a piece entitled “The Celtics’ Year-Long Pursuit of Paul George That Fell Short” which detailed the trade offers the Celtics made for George. Himmelsbach reported that at the 2017 trade deadline, Boston offered the Pacers four first-round picks, including the one which became the top pick in the 2017 draft; ahead of that draft, the Celtics offered “three starters and two first-round picks.” The Pacers ended up getting two future All-Stars for George—Victor Oladipo and Domantas Sabonis, but neither player seemed like a star at the time. The Pacers must have had incredible foresight to turn down the seemingly franchise-changing war chest offers made by Boston.
I’m breaking the rules a bit here—the Celtics’ 2014 chase to land Love was primarily reported before his eventual trade to the Cavaliers, not afterward as with all the other players on this list. But I had to include my favorite Almost Ainge tidbit of all time: Gary Washburn of The Boston Globe reported that Ainge was “dogged” in his pursuit of Love, but that the Timberwolves were demanding an unusually high return because they did “not want a repeat of that lopsided [Garnett] deal from seven years ago.”
Essentially, because Ainge ripped Minnesota off so badly before, it wanted to make extra sure he wasn’t ripping it off so badly again. Alas, it is the Curse of Ainge! What a cruel fate! To be so good at trading that nobody will trade with him!
The 2019 Anthony Davis trade saga was defined by his impending 2020 free agency. The Pelicans wanted to get something for their superstar center, but everybody knew that he would eventually make his own choice on his long-term destination (read: the Lakers). All along, it seemed pretty clear that Davis’s long-term destination would not be the Celtics. His father said he would never want his son to sign with Boston, and his agent warned the Celtics against trading for him. “They can trade for him, but it’ll be one year,” Rich Paul told S.L. Price of Sports Illustrated. “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. I’ve stated that to them. In the event that he walks away … don’t blame Rich Paul.” But Ainge could not be deterred. After Davis was eventually dealt to the Lakers, Paul told ESPN’s Dave McMenamin, “I don’t think it stopped Danny Ainge from trying. It’s just that maybe he didn’t have the deal he wanted. He wasn’t willing to give up the young players.” It’s never been reported what the Celtics were offering.
The Celtics’ involvement in the Davis trade market may be the most impressive thing Ainge has ever pulled off. Even though the Celtics were clearly not a serious destination for Davis, and trading for him likely would have been a disaster, he still managed to get it on the public record that he was fighting to pull it off anyway.
In this past abridged offseason, the Celtics were reportedly hard at work on a sign-and-trade that would have sent Gordon Hayward to Indiana. At the time, it was reported that Indiana offered Myles Turner and Doug McDermott, but the Celtics wanted Turner and Victor Oladipo. For a while, it seemed like the trade not materializing came down to Ainge pushing too hard. However, after Hayward instead signed with the Hornets, which got the Celtics nothing but the aforementioned trade exception that they have yet to use, ESPN’s Zach Lowe reported that the Indiana trade fell apart because the Celtics simply didn’t think Turner was that good. Lowe indicated that Ainge had asked around the league seeing what teams would offer him for Turner, and found that the trade market was lower than what the Pacers were making it seem.
It feels like the quintessential Almost Ainge story. The Celtics had a chance to land the guy who’s possibly going to win Defensive Player of the Year this season, and they were getting him essentially for nothing, since Hayward was leaving in free agency regardless. Ainge turned the deal down, and somehow, reports still surfaced highlighting his esteemed negotiating tactics. One report portrayed him as tenaciously pushing for a better return; another showed that he shrewdly outflanked the Pacers by testing the market for Turner before acquiring him. This is the legend of Almost Ainge. Even when the Celtics fail, we hear about how hard their general manager is working.
Nikola Vucevic, Aaron Gordon
As previously discussed, the Celtics almost got these guys a few days ago. It’s probably for the best that Ainge didn’t pull the trigger—I don’t see how these guys get playing time in the Butler-Kawhi-George-Davis frontcourt. Besides, Luke Kornet looks great.