Jrue Holiday is eligible for a contract extension on April 1, but the Boston Celtics may have already overplayed their hand by waiting to extend the 33-year-old after trading for him from the Portland Trail Blazers just before training camp.
If Holiday wants to explore his options in free agency, NBC Sports Boston's Chris Forsberg floated the Philadelphia 76ers as a potential threat to poach the former long-time Sixer during the offseason.
"Any decision — whether it’s to splurge or pivot -- gets a little easier if the Celtics win an NBA title this June," Forsberg prefaced before saying, "But waiting until the summer to tackle Holiday’s future also leaves open the possibility that he could opt out and explore other options.
"That’s somewhat daunting when you consider a contending team like the Philadelphia 76ers will have available cap space this summer. Just think back to 2019, when Al Horford surprisingly elected to opt out of the final year of his deal — albeit after a maddening Celtics season filled with drama and a disappointing finish — to sign with the 76ers. Horford and Holiday share the same agent in Jason Glushon, who also represents the recently extended Brown and the soon-to-be payday-seeking Sam Hauser."
Tyrese Maxey's next Sixers contract and Derrick White's next Boston Celtics contract to strongly influence Jrue Holiday free agency
Holiday's free agency decision will be dictated by his current and prospective future backcourt mates in Boston and Philadelphia, respectively: Derrick White and Tyrese Maxey, who are due for extensions next offseason (in White's case) and this summer (in Maxey's).
White and Holiday would likely get extended if the Cs win the championship this June. Banner 18 is all the justification needed to keep every key piece under team control for as long as possible, and paying everyone well would keep the group happy enough to continue building a prospective dynasty. Failing to win a championship this season forces Brad Stevens to strategically choose who not to overpay for, opening the door for Holiday to feel disrespected and leading to a potential bidding war for his services.
The Sixers may not even have the funds to steal Holiday, though, if they overplay their own hand by overpaying for Maxey. Averaging a career-high 25.8 points per game on a 45/38/86.7 shooting slash and buoying Philly in the absence of Joel Embiid for most of the 2023-24 season, Maxey may ask for the Brinks truck to be backed up.
Holiday's free agency is far from cut and dry until the contenders to sign him sort out their younger and more long-term pieces first.