The reigning 2024 NBA champion Boston Celtics have enjoyed a successful season, as the group’s most recent 114-108 victory against the Utah Jazz on Monday night gave them five consecutive wins and boosted their record to 47-18, good for the No. 2 seed in the Eastern Conference.

Though Boston looks to be primed for back-to-back title wins, it’s hard not to wonder how the offensive regression of point guard Jrue Holiday will factor into their run during the 2025 NBA Playoffs.

Even with a reputation as one of the league’s best defensive players in recent history, his current averages of 10.7 points and 3.6 assists on just 43.9% shooting from the field at age-34 could spell a major personnel shake-up for the storied organization.

In fact, it’s not impossible to believe that Boston’s front office could attempt to package the two-time NBA champion guard in a deal this summer to acquire surging All-Star snub Norman Powell and valuable two-way role player Derrick Jones Jr. from the Los Angeles Clippers.

While it may seem bizarre for either team to take part in these hypothetical negotiations, the premise of Powell and Jones Jr. ending up with Boston while Holiday heads to the Clippers could make sense on paper.

The Clippers possess the NBA’s current No. 3 defense (109.5 defensive rating), and the franchise may decide to fully lean into maintaining a defensive identity to support former league MVP James Harden and two-time Finals MVP Kawhi Leonard by acquiring arguably the best pound-for-pound defender in the entire Association in Holiday.

For Boston, the team would wipe Holiday’s four-year, $134 million contract from their books by landing Powell, who will be under contract for one more season before becoming an unrestricted free agent in the summer of 2026.

The 2019 NBA champion and former Sixth Man of the Year candidate could help to provide Boston with even more of a scoring punch outside of the deadly duo of Jayson Tatum and Jaylen Brown, as he’s contributed 23.8 points and 3.5 rebounds while knocking down 42.4% of his looks from three-point range for the Clippers this season.

Powell is also an improved defender, boasting a career-best figure of 1.3 steals and a solid 113 defensive rating per 100 possessions.

Jones Jr. is also no slouch on the defensive end, as the 28-year-old high-flying forward’s career 0.4 defensive box plus-minus and 36.7% accuracy from distance for Los Angeles this year has turned him into one of the more sought-after wings in the league.

By slotting Derrick White in as the Celtics’ new starting point guard in this scenario to make room for Powell, the Celtics’ starting rotation would become even more of an offensive juggernaut while their reserve depth would be revamped with the addition of Jones Jr., who helped the Dallas Mavericks to a 2024 NBA Finals appearance last season.

The possibility of a transaction of this nature going through is admittedly unlikely, but Boston will eventually have to make a decision on what they’d prefer to do with Holiday’s contract moving forward.