Celtics Predicted to Land 9-Time NBA All-Star After Anfernee Simons Trade

The Boston Celtics will land Damian Lillard after the nine-time All-Star guard was waived by the Milwaukee Bucks, Bleacher Report’s Greg Swartz predicts.

“Boston is under no pressure to win next season with Jayson Tatum nursing his own Achilles injury, but should be back in the title picture in 2026-27, assuming he, Jaylen Brown, Derrick White and Payton Pritchard are all still on the team. Adding Lillard to the core on a team-friendly deal now could be a smart investment,” Swartz wrote.

Lillard landing in Boston is contingent on the Celtics flipping Anfernee Simons to shed more salaries, according to Swartz.

ESPN’s Brian Windhorst reported on “The Hoops Collective” podcast that team president Brad Stevens and the Celtics are “actively” looking to trade Simons this summer.

“I have talked to other teams that have said the Celtics are actively trying to trade Anfernee Simons,” Windhorst said. “Whether they can or not is another [thing].”

The Celtics could open up their $5.7 million taxpayer mid-level exception to use on Lillard if they are successful in re-trading Simons, who arrived in Boston as part of the Jrue Holiday deal.

“The last time the Celtics got a veteran point guard from the Milwaukee Bucks, it ended pretty well,” Swartz wrote, referring to Holiday, who helped the Celtics win their 18th NBA championship last year. “Boston and Lillard should have mutual interest now.”

Celtics Among Teams Interested in Damian Lillard

Getty (L-R) NBA star Damian Lillard, Women’s Basketball Hall of Fame and Naismith Memorial Basketball Hall of Fame member Tina Thompson and Jared Vanderbilt of the Los Angeles Lakers attend a game between the Los Angeles Sparks and the Las Vegas Aces.

Lillard sent a strong message amid the Celtics and several contending teams’ reported interest in signing him while he is still on the mend.

“If they call it a ‘gamble’ at this stage… tell ’em this [is] the jackpot. #ToBeContinued,” Lillard posted on X on Thursday, July 3.

The Bucks stunningly waived Lillard to sign center Myles Turner in free agency.

The Celtics are among the group of teams that would want to sign Lillard even if he is expected to miss next season while recovering from his Achilles injury, according to The Athletic.

“Not surprisingly, league sources say Lillard received calls from several contending teams quickly after the news of his Bucks’ ending broke. League sources say the Golden State Warriors, Boston Celtics and Los Angeles Lakers are known to be among the many teams that would have interest in doing a deal sooner rather than later,” per The Athletic report.

Damian Lillard Taking His Time

Sam Amick of The Athletic reported shortly after the Bucks decided to waive Lillard and stretch the remaining $113 million on his contract that the 34-year-old point guard was “elated” as it afforded him freedom to choose where he plays next without financial constraints.

Lillard can sign for the minimum and still earn the $113 million the Bucks owe him, albeit stretched in five years with equal $22.5 million payments.

According to NBA insider Chris Haynes, Lillard is open to signing with a team this offseason while undergoing rehabilitation from his devastating injury, but it will only happen “under the right terms and conditions.”

Those terms and conditions were not disclosed.

Lillard can have a Jayson Tatum, who is also recovering from an Achilles injury, as his classmate during his rehab if he chooses Boston.