After a season that began with championship expectations in Milwaukee, Damian Lillard now finds himself sidelined with a torn Achilles and without a team. The Bucks’ decision to waive the 34-year-old guard earlier this month was abrupt but not entirely unexpected, given Milwaukee’s bloated salary sheet and growing uncertainty about the roster’s long-term viability. What’s more surprising is a possible landing spot that hadn’t been seriously considered last summer: Boston.

 With Jayson Tatum reportedly nursing a long-term injury, the Celtics are scanning the market for temporary firepower to stabilize the team’s scoring load. Team president Brad Stevens has a track record of taking calculated risks on high-upside veterans dealing with injuries—think of his gamble on Kristaps Porziņģis or Malcolm Brogdon in years past. And while no official offer has surfaced yet, internal buzz linking Lillard to Boston has gained real traction among insiders who believe the move could align with the Celtics’ short-term needs.

Still, the interest in Lillard isn’t just about scoring averages or injury timelines—it’s about context. In Milwaukee, Lillard was often seen clapping from the corner while the Bucks offense ran through Giannis, a stark shift from his alpha role in Portland. Even in late-game situations—his traditional domain—he frequently deferred, which drew subtle but pointed frustration from longtime fans and even some former teammates, according to local media reports. His brief stint there exposed how uneasy he looked operating in the shadows. In Boston, that dynamic would be different. With Tatum likely sidelined and Brown still more comfortable as a slashing secondary option, there’s a clearer opening for Lillard to reassert control in crunch time. The 2021 version of Lillard could finally be back. It is something Kevin O’Connor, Bobby Manning, and Noa Dalzell of The Golden Report touched base on.  

O’Connor stated that a team-up with Jayson Tatum and Co. may greatly appeal to Lillard, since“You don’t have to be the guy when you get back. You have Tatum, you have Brown, you have Payton Pritchard, for that matter. Like you can rest, you can, you know, load manage, you recover from the Achilles injury”. 

The trio pointed out one player who may struggle for minutes because of Lillard’s potential arrival: Payton Pritchard. Manning stated that Dame “might hurt Pritchard’s minutes.” But Noa Dalzell looked at the positives, as she added, “I’m all about the team, you know, maximizing the opportunities. And honestly, like, if Payton Pritchard is who I think he is, then…. who I think he can become, like then like, there’s…. an addition of another guard is only going to be a beneficial thing. And if he’s not, then there better be another guard on the way because then next year is a big opportunity for him, but also a big challenge, right?” 

For the hosts, adding Damian Lillard would do more than just provide the Boston Celtics with some more offensive firepower. It would give Payton Pritchard either a mentor or a challenger, both of which would compel him to push himself to the edge and give his best. After all, if you have to compete against a player like Lillard for the primary point guard position, you cannot give anything less than your A-Game.

During the 2024-25 NBA regular season, Payton Pritchard played for a total of 80 games and averaged 14.3 points, 3.8 rebounds, and 3.5 assists. He shot 5.1-10.8 (47.2%) field goals, 3.2-7.8 (40.7%) 3-pointers, and 0.9-1.1 (84.5%) free throws. His contribution as one of the Boston Celtics’ top offensive players was highlighted when he was named the recipient of the Sixth Man of the Year Award for the 2024-25 season. Winning the honor with 82 out of 100 first-place votes highlighted his importance to the Celtics.

However, Damian Lillard carries 8 additional years of NBA experience. Given his star power, the Celtics would want to prioritize him. Since Derrick White is the primary point guard, the fight will be for the secondary position, which in turn would lower the 28.4 minutes per game that Pritchard had been averaging. That is, if Pritchard decides to stick around and fight for his place.

On the other hand, maybe Payton Pritchard won’t have to take up the pressure. After all, the Boston Celtics are not the only team interested in the veteran.

Will Damian Lillard go to the Miami Heat?

During the same episode of ‘The Garden Report’, Kevin O’Connor asked a question that Lillard’s agent ought to ask him.“If you’re Damian Lillard, do you want to go to a team where you might be the backup point guard to Payton Pritchard, you know, or to Derrick White and these guys, or do you want to go to a team where you’re going to be the starter, and you’re going to get opportunities to go back and be Damian Lillard again?”

During his time with the Bucks, Lillard was largely in the shadow of Giannis Antetokounmpo (like everyone else in Milwaukee!). And now he might wanna be the main guy. Drumrolls…in comes the Miami Heat. And as O’Connor added, ” a team like the Miami Heat” offer him the chance to be the main guy.

But as with everything in life, this move also has its set of disadvantages. And Noa Dalzell touched upon them, “I think the reality, though, is that we all know where Damian Lillard’s head was at two years ago. He wanted to go to Miami. He, you know, the reporting has been that he misses his kids, who are in Portland. So, to me, it’s like there are some geographic things, like maybe he wants to be near home, and on the West Coast.” Lillard has spoken about being homesick during previous instances as well. For instance, after his injury in the postseason, Lillard decided to undergo rehabilitation in Portland, a city he called home for 11 years.

Dalzell also admitted, “Like, I don’t really know where Boston fits in. Like, I would love to see him in Boston, but I feel like it’s a little bit of like Celtics fans, like, kind of looking for something to be excited about. And I hope I’m wrong because I would love to see him in Boston”. She is absolutely right. With Jayson Tatum already set to miss, if not the entirety, then the majority of next season, Celtic fans may not be very excited if they decide to pick up another sidelined player in Damian Lillard.

Damian Lillard’s family, aka his ex-wife Kay’la Hanson and 3 children, live in Portland, Oregon. During an interview with Damian Lillard back in February 2024, the player admitted that he didn’t have much of a life since moving to Milwaukee, and that being away from his then-wife and family had been hard. With the NBA player’s ex-wife having filed for sole custody last year, Lillard had to prove to be more of a father figure. One way to do that is to be closer to Portland. He can’t do that in Miami or Boston.

It remains to be seen what move Lillard makes for his future…but one thing is sure, his family will play a massive role in that decision.