Celtics reportedly may have to attach draft picks to trade Jrue Holiday

Jrue Holiday who turns 35 years old in a couple weeks was a key member of the Boston Celtics 2023-24 NBA championship team. Brad Stevens traded a lot to add Holiday two offseaons ago in starting center Robert Williams, Sixth Man of the Year Malcolm Brogdon (who Stevens had traded Aaron Nesmith and a 1st round pick for a year prior) as well as two more first round picks.

While trading what amounted to Robert Williams, Aaron Nesmith, and three first round picks for Holiday was a ton, the championship last year made it worth the while. The decision to ink Holiday to a very lucrative new long term contract for his mid to late 30's though may cause some regrets for the Celtics front office though.

When trading for a veteran player its quite common to then get less if you flip them two years later, but after giving up what amounted to two recent 1st rounders and three additional first rounders in order to obtain Holiday, the fact that two years later Jrue has negative trade value according to multiple rival executives is a tough pill to swallow.

The Celtics reportedly will need to attach first round draft compensation to move on from the remaining $104 million owed to Holiday. Note that despite Holiday's drop in performance this past season the fact that he has negative trade value isn't meant to say that he's a lousy player. He's not. Holiday is still a winning player who every contender would want on their team... if he was being paid like let's say Al Horford ($10 million).

Holiday's inflated $35 million per year deal is what causes him to have negative trade value. If it was an expiring deal, that wouldn't be the case. But if you trade for Holiday you have on the books through 2028.

In order to trade a player with negative trade value you either need to take back a similar player with negative trade value or attach draft picks to get back a player who doesn't have negative value.

Considering the Celtics are under a mandate to cut payroll due to the 2nd apron and tax they need to get back a player making a lot less than $35 million a year. In the end the Celtics may have to trade Holiday for a worse player andattach a first round pick or two in order to get off from his contract.

If Stevens could simply trade Holiday for nothing just to get off from his contract he would. But that would would only be the case if Holiday, again due to his contract, didn't have negative value. To find a team with cap space that could take back Holiday, Stevens would have to throw in likely 3 first round picks, which would be a non-starter considering Boston already owes future first round picks and pick swaps to Portland and San Antonio.

Stevens instead could trade for a player (or players) who make less than Holiday and that would cost less in draft capital. The only way for Stevens to trade Holiday and not have to give up a first round pick (or picks), all the while reducing the team's tax bill would be to trade him for a considerably worse player who is also overpaid, but makes less than $35 million per year.

As one can see, Stevens is in a difficult postion where he's trying to remain a contender for when Jayson Tatum returns, while at the same time trading away talented players for worse players. Thea catch 22 is that the only way for the team to remain a contender despite the loss of core rotation players will be to add new core rotation players that are underpaid. The main way to do that is to draft them, but if every other team is requiring draft picks in order to alleviate the Celtics' financial woes, that becomes impossible.

Stevens has a championship to hang his hat on and all of Boston's local media and fans fawn over his every move, but he decided to invest in lucrative contract extensions for Holiday and Porzingis all the while re-signing both Jay's to super max deals. He also has traded several first round picks which further limits his options. Point is eventually all that catches up to a general manager and that time is just about now.

When the dust settles and if Stevens was somehow able to retain Tatum, Brown, and White while simultaneously bringing in the new pieces necessary to round out a contending roster, without completely trading away the team's future first round picks, and that group wins another title, then yes Stevens will have earned all the accolades he receives.

Winning a title with the group he inherited from Ainge was actually the easy part when you compare it to trying to win another with the restraints he now has. Considering what its sounding like the cost will be to dump Holiday's contract, Stevens really needs to pull of an Auerbachian move here.