The Boston Celtics face a pivotal offseason, with de facto GM Brad Stevens at the helm of a franchise navigating a delicate balance between immediate competitiveness and long-term sustainability. With Jayson Tatum sidelined, the Celtics are unlikely to contend for a championship next season, making this the perfect moment to retool the roster. Stevens has a golden opportunity to reshape the team’s future by acquiring draft capital and younger talent, setting the stage for a new era of Celtics basketball. However, standing in his way is a familiar foe: Danny Ainge, the former Celtics GM now running the show for the Utah Jazz. Ainge, known for his cunning trades, could be poised to outmaneuver Stevens and “rob the Celtics blind” once again in a deal that could send shockwaves through the NBA.
A Critical Offseason for Boston
The Celtics’ roster is at a crossroads. Aging veterans like Jrue Holiday and Kristaps Porzingis, both on expensive contracts, could be moved to clear cap space and make way for younger players. With Al Horford and Luke Kornet set to hit free agency, the team has glaring needs at power forward and center. Stevens holds two draft picks in the upcoming NBA Draft — a late first-rounder (No. 28) and an early second-rounder (No. 32) — but these selections may not yield players capable of addressing immediate needs. Trading up to secure a higher pick or trading down for future draft capital could be the smarter play, especially with Tatum’s eventual return in mind.
Enter Danny Ainge and the Utah Jazz, who hold a treasure trove of draft picks and trade assets that could tempt Stevens into a blockbuster deal. Ainge, who once orchestrated one of the most lopsided trades in NBA history by sending Kevin Garnett and Paul Pierce to the Nets for picks that became Tatum and Jaylen Brown, is no stranger to outsmarting his counterparts. Now, with the Jazz rebuilding, Ainge could exploit Boston’s urgency to reset, potentially leaving Stevens and the Celtics reeling.
The Jazz’s Draft Haul and Trade Chips
The Utah Jazz, coming off a dismal 17-65 season, had their sights set on the No. 1 pick and Duke phenom Cooper Flagg. However, the draft lottery dealt them a blow, dropping them to No. 5. Despite the setback, the Jazz are loaded with draft capital, holding picks No. 5, 21, 43, and 53. They also boast two valuable trade assets in Lauri Markkanen, a versatile stretch big, and John Collins, a high-energy forward. According to Jazz writer Sarah Todd, Ainge is open to moving picks No. 21, 43, and 53, though the No. 5 pick is likely untouchable given the talent available in this year’s draft.
For Stevens, the Jazz’s draft picks represent a chance to either move up for a player who can fill Boston’s frontcourt void or acquire future picks to bolster the roster when Tatum returns. Markkanen, in particular, could be an ideal target — a 7-foot sharpshooter who would address the uncertainty surrounding Horford, Porzingis, and Kornet. However, Ainge’s history suggests he’ll drive a hard bargain, potentially fleecing Stevens in a trade that could haunt Boston for years.
Ainge’s History of Outsmarting Boston
Ainge’s track record speaks for itself. In 2013, he orchestrated the Garnett-Pierce trade, securing draft picks that became the cornerstone of Boston’s current core. Now, with the Jazz in rebuild mode, Ainge is in a position of strength. He knows Stevens is under pressure to make bold moves, and he could exploit that desperation. A trade involving Holiday or Porzingis, both aging players with hefty contracts, might not appeal to Ainge unless Stevens sweetens the deal with additional assets — perhaps even Boston’s No. 28 pick or future draft capital.
For example, Ainge could demand the No. 28 pick and a future first-rounder in exchange for No. 21 and a second-round pick, giving the Jazz more flexibility while leaving Boston with less to build around. Alternatively, if Stevens pushes for Markkanen, Ainge might insist on a package that includes one of Boston’s young prospects, further depleting the Celtics’ depth. Either way, Ainge’s knack for extracting maximum value could leave Stevens in a precarious position.
Stevens’ Path Forward
Stevens isn’t naive — he knows Ainge’s playbook better than anyone, having worked under him during Ainge’s tenure in Boston. To avoid being outmaneuvered, Stevens must approach negotiations with caution. A trade for Markkanen could transform the Celtics’ frontcourt, but only if the price is right. Alternatively, Stevens could focus on moving down in the draft, trading No. 28 for future picks to ensure Boston remains competitive when Tatum returns. The relationship between Stevens and Ainge could facilitate open dialogue, but it also means Ainge knows exactly how to push Stevens’ buttons.
A Trade That Could Shock the NBA
As the NBA Draft approaches, all eyes will be on Boston and Utah. A blockbuster trade between the two teams could reshape the league, with Ainge potentially fleecing his former protégé in a deal that echoes the Garnett-Pierce trade. Whether it’s a swap for Markkanen, a move up in the draft, or a package of future picks, the outcome of this offseason could define the next era of Celtics basketball. If Ainge gets his way, he’ll once again prove why he’s one of the shrewdest GMs in the game — and the NBA will be left in awe.