The Boston Celtics are sitting comfortably as the Eastern Conference’s No. 2 seed with a 39-16 record while aiming to repeat as NBA champions in 2025.

Boston’s dominance in the Eastern Conference for the better part of the past decade was finally validated in 2024 with an NBA Finals victory over the Dallas Mavericks, but the franchise may have to make some tough decisions this summer whether they come away as champions for the second consecutive season or not.

Due to increasing financial instability now that Boston’s front office has planned to pay superstars Jayson Tatum and Jaylen Brown a combined $562 million through the 2028-29 season, they’ve placed themselves in a tricky predicament. Specifically, the future of the Celtics’ aging two-time NBA champion and two-time All-Star point guard Jrue Holiday may be in question.

While Holiday has provided meaningful contributions to the team over the past few seasons, the 34-year-old’s 11.0 scoring average is his lowest output since his rookie season in 2009-10, though he’s managed to remain a lethal defensive guard sporting a 112 defensive rating per 100 possessions.

With decreasing shooting splits and the opportunity for Holiday to accept a $37 million player option at 37 years old with Boston in the summer of 2027, the Celtics’ general manager Brad Stevens may look to swap Holiday for a fellow two-time NBA champion and two-way contributor from the Orlando Magic, Kentavious Caldwell-Pope this offseason.

Though Caldwell-Pope is still a tenured option at the shooting guard position at 32 years old, his contract would be manageable for the Celtics moving forward after a potential Holiday swap.

After winning his second NBA title as a member of the Denver Nuggets in 2023, Caldwell-Pope decided to sign with the Magic in the summer of 2024 to be the team’s marquee free agency addition due to his shooting prowess and reputation as a skilled perimeter defender.

In 53 appearances with Orlando, Caldwell-Pope’s numbers have also unfortunately declined. The 12-year veteran is contributing 8.7 points paired with a 50.6% effective field goal percentage, which might not look appealing to Boston at first glance. On the other hand, his $21 million salary and shorter contract length could sway the Celtics towards making the fiscally responsible decision to pursue him as a trade target.

By making a hypothetical trade for Caldwell-Pope, Boston would lose their trusted starting point guard in the process.

However, the improved play-making of star Celtics guard Derrick White could lead the 6-foot-4 combo-guard to become the team’s future floor general. After a Sixth Man of the Year and Most Improved Player campaign this season, Boston’s Payton Pritchard could also be due for a promotion to the starting lineup in the event that Holiday were to be shipped out. 

Boston’s bevy of options to replace Holiday as the team’s point guard could very well be the factor that makes saying goodbye somewhat easier, while the defensive-minded Magic would plausibly be excited to welcome the six-time All-Defensive Team selection into the fold.

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