The Boston Celtics remain active in the trade market as they continue their roster retooling process under President of Basketball Operations Brad Stevens. After trading Jrue Holiday and Kristaps Porzingis, the team is considering further transactions, with players like Anfernee Simons and Georges Niang potentially being moved before the start of the upcoming season. Recent discussions with other teams, including the Memphis Grizzlies, suggest that Boston is still exploring options.

Stevens' strategy is focused on building a championship contender, particularly as star player Jayson Tatum recovers from an Achilles tendon injury. The Celtics have time to make savvy moves without rushing, although fans may have to brace for a challenging season as part of this long-term vision.

The Boston Celtics recently missed out on securing Damian Lillard, who opted to sign with the Portland Trail Blazers for a lucrative three-year deal worth $42 million. Despite attempting to keep their offers competitive, the Celtics' financial limitations, as they work to avoid the luxury tax, hindered their pursuit. General Manager Brad Stevens made moves by trading Jrue Holiday and Kristaps Porzingis to ease their financial situation.

Lillard's fit with the Celtics was already questionable, given his need for the ball in his hands. The uncertainty surrounding his performance following an Achilles injury also raised concerns, especially with him nearing 36. Now that Lillard is off the table, Boston's management must continue evaluating ways to rebuild their roster, targeting a return to contention as Jayson Tatum recovers from his own Achilles injury expected by the 2026-27 season.

Damian Lillard enters free agency for the first time in his career after the Milwaukee Bucks waived him. The five-year, $20 million per year contract offers him flexibility, but he is currently sidelined due to a ruptured Achilles tendon. As Lillard undergoes rehab, teams are eager to sign him, with the Golden State Warriors emerging as a potential destination alongside the Boston Celtics, Miami Heat, and Minnesota Timberwolves. While the Celtics are the frontrunners, the Warriors, led by veterans Stephen Curry and Draymond Green, present an intriguing option for Lillard.

Historically, Lillard faced the Warriors in the playoffs during his time with the Portland Trail Blazers, winning only one game across three series. His future is uncertain, but his impact could significantly change any team’s dynamics.

Damian Lillard's free agency came to a close as he signed a three-year, $42 million deal with the Portland Trail Blazers, marking his return to the franchise where he spent the first 11 years of his career. After averaging 25.2 points and 6.7 assists during his time in Portland, Lillard's recent stint with the Milwaukee Bucks saw him waived this offseason. Now, he will likely focus on recovery from a torn Achilles suffered in the playoffs last season.

The Boston Celtics showed interest in Lillard prior to the signing, offering minimum and mid-level exception contracts. He is set to earn a staggering $70 million next year due to contracts with both the Bucks and Blazers, totaling $140 million over the next two years. The Celtics now have to explore other options as they pivot away from pursuing Lillard.

The Boston Celtics are making significant moves this offseason, highlighted by the departure of Jrue Holiday and Kristaps Porzingis as they navigate their financial landscape. With Jayson Tatum sidelined for the entire season due to a torn Achilles, the Celtics are in a rebuilding phase while hoping to secure a playoff spot led by Jaylen Brown and Derrick White. Anfernee Simons, acquired in the Holiday deal, could be on the trading block before even stepping onto the court for Boston, with potential trades being discussed.

One such trade would send Simons to Memphis in exchange for Brandon Clarke and other assets, which could enhance Boston's wing depth and provide another big man to their rotation. This move may be appealing to Memphis, given their recent need for scoring following Desmond Bane's exit. With various trade options available, Boston's front office has a lot to consider as they aim to balance depth and potential for next season.