Of all the teams bargain-hunting in the Damian Lillard sweepstakes, the Boston Celtics are uniquely suited to help him write his best comeback story post-Achilles rupture.
What sets Boston apart from the rest of the field, first and foremost, is Lillard’s good friend Jayson Tatum, who has reportedly made efforts to recruit the injured guard to the Celtics. Tatum tore his Achilles just weeks after Lillard sustained a similar injury, then playing with the Milwaukee Bucks. Tatum and Lillard were teammates representing the U.S. in the 2020 Olympics. Lillard shared an Instagram post with in May featuring Tatum and a "fingers crossed" emoji in the caption.
NBA players recruiting their buddies is nothing special in and of itself. But when have two friends sustained the same dramatic injury, weeks apart? There are few things in professional sports that sound lonelier than a 9-to-12-month injury rehab completely alone – and that’s what Lillard faces. He doesn’t appear to be in any hurry to sign with a new team. Milwaukee will pay the $112 million he’s due over the next two seasons regardless of what he does in the meantime. I’m not saying Tatum and Lillard will be side-by-side, working out in Auerbach Center, every day of 2025-2026. But they can support one another, in person, through a rehabilitation process that Kobe Bryant once described as “unbearable.”
Lillard would also join a team likely to be, at worst, in spitting distance of championship contention. It’s foolish to try to predict how the league will look in the wake of an entire season after one that hasn’t even started. But he would join a probable core of Tatum, Jaylen Brown, and Derrick White – two All-NBA players and a fringe All-Star candidate who is perpetually underrated. He could return to hooping without the weight of the world on his 35-year-old shoulders, but play a critical role in a championship run in 2027. Boston is a place where it will be okay if Lillard doesn't play more than 30 minutes a game, or reach his 24.9 points per game pre-injury average. Two Celtics guards (Malcolm Brogdon, Payton Pritchard) have accounted for 50% of the NBA Sixth Man of the Year winners in the last four seasons. That honor would be an individual tale of redemption, on top of chasing a ring.
Finally, the Celtics can deliver a sizable paycheck to Lillard to get healthy in the upcoming year. They can use the taxpayer’s mid-level exception, roughly $5.7 million, as an offer on top of his stretched contract with Milwaukee.
So maybe Chris Haynes laughed off Lillard going to Boston back in 2023. That’s fine, no hard feelings here. Things have changed for both sides. The circumstances that have brought a possible union together are brutal, but the silver lining may be serendipitous.