Boston Celtics team president Danny Ainge is the king of *almost* acquiring every available star on the NBA trade market.
If a star became available in the NBA over the past five years, the Boston Celtics almost certainly sniffed around at some point.
Armed with a cache of draft picks and promising prospects from his pillaging of the Brooklyn Nets in 2013, team president Danny Ainge could cobble together an enticing package for any star. However, he had to balance the urge to go all-in with a long-term team-building approach.
Ainge has made a few notable moves in recent years, including the acquisition of Isaiah Thomas at the 2015 trade deadline, trading down from the No. 1 pick in 2017 to select Jayson Tatum and flipping Thomas during the 2017 offseason in a package for Kyrie Irving. But he’s become notorious for the trades that he hasn’t made over the past few years, too.
Heading into the 2021 trade deadline, the Celtics are once again in a position to make a huge splash thanks to their record $28.5 million traded player exception from the Gordon Hayward deal this past offseason. But if Ainge’s recent history is any indication, they’re more likely to almost acquire a star than actually snag one.
6. The No. 9 pick in 2015
Before turning his attention to basically every available superstar in the NBA, Ainge desperately wanted to land Justise Winslow in the 2015 draft.
According to ESPN’s Chris Forsberg, the Celtics offered a “package featuring as many as six draft picks, including four potential first-round selections” to the Charlotte Hornets for the No. 9 pick. However, the Hornets rebuffed them and chose Frank Kaminsky with that selection, while the Miami Heat snagged Winslow at No. 10.
Forsberg didn’t specify the protections on the picks in Boston’s offer—”four potential first-round selections” may be doing a ton of heavy lifting in that sentence—but Ainge was relieved that the Hornets didn’t take him up on it.
“In hindsight, the next day, it’s probably a good thing,” he said on 98.5 The Sports Hub after the draft, per Rick Bonnell of the Charlotte Observer. “We were probably going to spend too much to do what we needed to do.”
The Celtics instead stood pat at No. 16 and took Terry Rozier, who starred in their run to the 2018 Eastern Conference Finals.
5. Paul George
Before adding Jayson Tatum and Gordon Hayward during the 2017 offseason, the Celtics had their eyes on another star forward.
Ahead of the 2017 NBA trade deadline, the Celtics had a “preliminary talk” with the Indiana Pacers about Paul George, according to Adrian Wojnarowski (then of The Vertical). However, he noted the two teams wouldn’t have “real dialogue until/unless” the Celtics were willing to add the Brooklyn Nets’ 2017 draft pick into the deal.
The Celtics did eventually include that Nets pick in their negotiations, per Wojnarowski, but they failed to meet Indiana’s “asking price” prior to the trade deadline. According to Adam Himmelsbach of the Boston Globe, they offered the Nets first-rounder — which wound up being the No. 1 overall pick — along with “three other future first-round choices,” but the Pacers didn’t bite at the time.
That didn’t stop the Celtics from circling back prior to the 2017 NBA draft, though.
A few days after George told the Pacers that he planned on leaving as a free agent in 2018, talks between Boston and Indiana “had gained significant momentum,” according to Wojnarowski. However, Woj said the Celtics never made a “real offer” (h/t Jared Weiss of The Athletic) for George before the Pacers shipped him to the Oklahoma City Thunder for Victor Oladipo and Domantas Sabonis.
Both Himmelsbach and ESPN’s Jeff Goodman reported the Celtics offered the Pacers three first-round picks and two starters (including Jae Crowder) on the night of the 2017 draft, but they reportedly weren’t willing to include the Nets’ 2018 first-rounder or the Sacramento Kings’ 2019 first-rounder. Steve Bulpett of the Boston Herald confirmed their refusal to include either pick in their offer.
The trade worked out well enough for the Pacers, as Sabonis developed into a two-time All-Star and they flipped Oladipo for Caris LeVert in the James Harden blockbuster in January. Meanwhile, the Celtics can only wonder how much havoc a trio of George, Tatum and Jaylen Brown would have wreaked across the NBA.
4. Jimmy Butler
Before the Chicago Bulls shipped Jimmy Butler to the Minnesota Timberwolves on the night of the 2017 NBA draft, the Celtics had come calling multiple times.
Ahead of the 2016 draft, 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,” according to K.C. Johnson of the Chicago Tribune.
“Several proposals were exchanged, including one with Jae Crowder and the Celtics’ No. 3 and No. 16 picks,” Johnson added. “But the Celtics have a reputation of trying to win trades and kept changing terms, none of which ultimately met the Bulls’ liking.”
When the Bulls began shopping Butler the following year, the Celtics sniffed around again.
“The Bulls were rebuffed on an offer to the Celtics for the third pick straight-up,” Vincent Goodwill reported for NBC Sports Chicago at the time. However, he noted the Celtics “have always been fond of Butler and have the assets the Bulls in theory would be attracted to in terms of multiple draft picks and affordable contracts on the current roster.”
The Timberwolves wound up sending Zach LaVine, Kris Dunn and the No. 7 overall pick (Lauri Markkanen) to the Bulls in exchange for Butler. The Celtics bowed out in part because they “had some concerns over how [free-agent signee Gordon] Hayward and Butler would mesh, both on the court and as personalities,” according to ESPN’s Zach Lowe.
The Celtics did acquire Kyrie Irving from the Cleveland Cavaliers later that summer, though.
3. Kawhi Leonard
When the San Antonio Spurs began shopping Kawhi Leonard during the 2018 offseason, the Celtics appeared ready to pounce.
They were “among [the] teams” who made offers to the Spurs for him, according to ESPN, and Wojnarowski noted “Boston has long had the assets that the Spurs most covet in a potential Leonard trade.” However, he added that the Celtics were being “extremely cautious on [the] Leonard front” because of the uncertainty with his future, and they had “no intention” of making a risky trade.
In early July, Wojnarowski said the Celtics had made their “top five players off-limits” and preferred to “do a deal that’s pick-heavy,” but the Spurs wanted “good players back.” The Toronto Raptors eventually swooped in and sent DeMar DeRozan, Jakob Poeltl and a first-round pick to the Spurs for Leonard and Danny Green.
The Raptors went on to win that year’s NBA title, while some people within the Celtics organization ended up feeling regret about “not pulling the trigger” on a Leonard trade, according to Chris Mannix of Sports Illustrated.
“Assuming what we know (about their pursuit) is true, it was questionable at the time,” one rival executive told The Athletic’s Jay King about the Celtics’ failure to land Leonard. “Now, it looks worse.”
2. Anthony Davis
The Celtics spent years gearing up for a run at Anthony Davis, according to Wojnarowski (via Tom Westerholm of MassLive). But when push came to shove, the Los Angeles Lakers wound up outbidding them leading up to the 2019 NBA draft.
In February of that year, Davis’ father told ESPN’s Ramona Shelburne that he would “never want my son to play for Boston after what they did to Isaiah Thomas.” A few months later, Davis’ agent, Rich Paul, told S.L. Price of Sports Illustrated that “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.”
That appeared to deter Ainge from offering his full war chest, according to Adam Himmelsbach of the Boston Globe. While Sam Amick of The Athletic reported in February that the Celtics and New Orleans Pelicans had discussed packages including Jayson Tatum, Marc Stein of the New York Times reported that they refused to include Tatum once trade talks heated up in June.
Instead, the Lakers wound up sending Lonzo Ball, Brandon Ingram, Josh Hart, three first-round picks and a pick swap to the Pelicans for Davis. Fortune favored the bold, as the Lakers immediately proceeded to win a championship in their first year with him in the fold.
Meanwhile, the Celtics frontcourt remains one of their biggest weak spots.
1. James Harden
The Brooklyn Nets wound up landing James Harden in January, but the Celtics sniffed around as well.
“Yeah, we had conversations regarding James,” Ainge said during an appearance on 98.5 The Sports Hub’s Toucher and Rich in mid-January (via Darren Hartwell of NBC Sports Boston). “Not recently, but yeah. We did have conversations.”
However, Sam Amick of The Athletic reported “Boston’s level of interest and involvement far surpassed what Ainge was willing to admit to when he addressed it publicly.”
Houston’s asking price was likely the deal-breaker. According to Sports Illustrated‘s Chris Mannix, the Celtics refused to part ways with Jaylen Brown in a Harden trade, but they didn’t have enough other enticing assets to beat the Nets’ offer.
Since acquiring Harden, the Nets have gone 20-7 and are one game behind the Philadelphia 76ers for the No. 1 seed in the Eastern Conference. The Celtics have gone 12-16 over that same stretch and are 7.5 games behind the Sixers.
Unless otherwise noted, all stats via NBA.com, PBPStats, Cleaning the Glass or Basketball-Reference. All salary information via Spotrac.
Follow @btoporek