According to a report from Gary Washburn of the Boston Globe, Celtics star Jayson Tatum has been actively recruiting Lillard to join him in Boston. He was on the Garden Report podcast, where he stated: “Tatum is the face of the franchise. So, yeah, we are told he’s recruiting. I don’t know if they’re like FaceTiming every day or they’re on Snapchat and sharing videos. … Like, I don’t know if it’s that deep, but they are communicating, and I think we all know Tatum’s going to be here for a long time.” At first glance, the fit seems odd.

Lillard had no interest in playing for the Celtics back in 2023 when he requested a trade from Portland. Instead, Heat was his desired destination, but he ended up with the Bucks, playing alongside Giannis Antetokounmpo. That partnership never really got off the ground because Lillard was constantly dealing with injuries. But a lot has changed since then. According to a recent report from the Boston Herald, Lillard is now more “receptive” to the idea of joining the Celtics. The timing, it turns out, might be perfect. Washburn believes that at age 35, Lillard’s approach has evolved.

“He’s open to new teams and obviously, he wants to win a championship. The only thing he does not have in his career is a title. He’s top 75. He’s going to the Hall of Fame. He’s fourth all-time in three-point makes. So the only thing Dame doesn’t have is a chip, or even getting close to one, right? I think it all depends on what he wants to do,” Washburn stated. And Lillard has an interesting message for his fans.

As Damian Lillard celebrated his 35th birthday, he embraced his new reality as a free agent. After a season-ending Achilles tear, the Milwaukee Bucks made the stunning decision to waive him, using the ‘stretch provision’ on the remaining two years and $112.6 million of his contract. It was a financial move, allowing them to sign center Myles Turner, but it also made Lillard the most intriguing name on the open market. And he knows it! So, now on his birthday, he shared a message on Instagram: “Forever Evolving and Rolling with the Punches! They can’t FW me! Cheers to 35! #ToBeContinued.” His ‘To Be Continued’ message points towards an exciting pivot in his basketball career.

Additionally, the Celtics are facing what is essentially a gap year after their own superstar, Jayson Tatum, went down with a devastating Achilles injury during the playoffs. With Tatum expected to miss most, if not all, of the 2025-26 season, the pressure to win now is off. This creates a unique, low-pressure environment for Lillard to rehab his own Achilles injury alongside a fellow superstar. Celtics President Brad Stevens gave an encouraging update on Tatum’s recovery two days ago, noting his competitive fire. “He’s a competitor. He’s gonna compete in everything he does, including rehab,” Stevens said.

But coming back to Lillard, the financial side of a potential deal is tricky. The Celtics can only offer Lillard a veteran minimum contract or a small $5.7 million exception. For a player who has already secured his financial future, the appeal of joining a team with a built-in championship culture, a fellow superstar to rehab with, and a clear path to contending in a year might be too good to pass up.

While Boston dreams of a Lillard-Tatum pairing, the Bucks are busy justifying the shocking move that made it all possible. For them, waiving a future Hall of Famer wasn’t just about moving on; it was a desperate all-in gamble to keep their own superstar, Giannis Antetokounmpo, happy and committed to Milwaukee.

Why the Bucks gambled on Damian Lillard’s exit

After another disappointing first-round playoff exit, rumors were swirling that Antetokounmpo was unsettled. The front office knew they had to make a bold move. That move was signing Myles Turner, a player they see as the perfect fit next to Antetokounmpo. Last week, Coach Doc Rivers admitted how difficult the decision was, calling Lillard a “great dude” who did “everything right throughout his career.” But, as he explained, “Stretching Dame’s contract, which was not easy to do… gave us more flexibility and we can sign more guys.”

The move, however, didn’t initially sit well with Giannis Antetokounmpo. But the front office went into damage control, outlining their multi-season plan and assuring him of their commitment to winning. It seems to have worked. “Giannis came to me the day after the season and we were talking about next season already,” Rivers told reporters. Bucks President Peter Feigin recently shut down any exit rumors, stating, “We kind of laugh internally… Giannis loves Milwaukee, Milwaukee loves Giannis. We’re in a good place.”

That “good place” seems to be reinforced by Antetokounmpo’s own focus this offseason. He recently posted photos of a family vacation with the caption, “I just want to collect memories with my forevers.” For a player who values loyalty, that focus on family is a good sign for the Bucks. It also likely means good things for his brother, Thanasis, who is expected to re-sign with the team now that Antetokounmpo appears to be staying put.

Still, the decision to mortgage their future, the stretched contract will leave over $22 million in dead money on their books for the next five years. The Bucks have made their bet, and they are continuing to push their chips in. The latest development saw them reach a buyout agreement with the Memphis Grizzlies for guard Cole Anthony, who is now expected to sign with Milwaukee.