Back in 2023 Boston was looking to add depth in their backcourt that came with the veteran energy and experience. The very first name that came to their heads? Milwaukee Bucks’ Jrue Holiday, who had already helped raise the championship trophy in Wisconsin in his very first season there. And the Celtics were looking to produce the same result. As it would, the Californian, with his leadership and dominance on both sides of the ball, brought a title to Boston in 2024. However, ever since Boston’s untimely 2025 playoff exit at the hands of the New York Knicks, reports have popped up about their front office’s decision to overhaul their squad and start anew. 

Sure, they are looking for better results after not even getting a chance to defend their title; but there’s a bigger backstory– The collective bargaining agreement (CBA)’s second apron. And the Celtics are now in a dire need to dodge a historic payroll and tax bill. Unfortunately, among others, at the center of it all is their defensive pillar with a heavy contract of $134 million/ 4 year– Jrue Holiday. While they have a burden of choices they need to make before the trade deadline drops, insider Bobby Manning has a “bold” suggestion to ease the pain.

Per MassLive’s report, Jrue Holiday and Kristaps Porzingis are among the first names on the hit list. Considering this, Bobby Manning suggested a trade on The Garden Report. “If Celtics are moving one of Holiday or Porzingis over to Detroit — I looked at a scenario where they could maybe move both, and then flip Hauser over to Brooklyn. That’s where things get a little convoluted and probably unlikely. But you know, if they’re trying to get below that second apron line, it’s probably going to take something bold like that,” opined Manning.

Now, a Jrue Holiday trade would certainly help the Celtics meet their goals of the squad overhaul they’re envisioning. See, their second apron is set at $207 million for next season. But, they only need to cut $20 million from their salary roll to be under it. And trading away Jrue would free up $32.4 million for them. Which means they would be comfortably under the second apron limit. But there’s a big ‘if’ hanging over their heads.

Turns out, other teams in the league respect Holiday. Despite turning 35, while his offense might have tumbled, his defensive presence and leadership, that have led to Boston become a title contender and raise the trophy are still intact. In his second season with the team, he added 11.1 points, 4.3 rebounds, and 3.9 assists while shooting 44.3% from the field. But the Celtics would need to find a trade partner who can take on Holiday’s hefty contract. Not to mention also be inclined to part with the draft capital to get him. Which brings us to the other options that Boston still carries.

Will it be Jrue Holiday who will leave the Celtics?

See, we did tell you that change was coming to Boston this summer. However, the exact nature of that change seems uncertain. Countless rumors are flying around about who will leave the Celtics in the 2025 offseason. We just discussed a Jrue Holiday trade based on what Manning said, so let’s look at some other options.

Sam Hauser and Kristaps Porzingis are among the likeliest players to get traded out of Boston this summer. If they trade Hauser, they will cut around $90 million in salary and luxury tax without even having to recoup any money. But it’s still only frees up $10 million in terms of their apron limit.

Meanwhile, despite Porzingis producing great numbers, concerns around his health and fitness mean he is at his most expendable right now. And his $30.7 million salary also slots in nicely as a way to stay under the $207 million second apron limit. So, if pitted head-to-head, trading the Latvian would make far more sense than trading Hauser.

Beyond that, there are also rumors of Jaylen Brown being traded. And this will definitely upset some Celtics fans. However, the CBA is merciless. So, if the Celtics see a worthwhile offer that they may think is too good to pass up, they may go for it. Similarly, they may also consider trading an aging Derrick White for a fresh face. After all, his $28.1 million salary also helps them stay under the second apron.

All in all, it’s hard for the Boston Celtics to make a decision on it right away. They have a lot of tradeable players, and anyone could help them with their financial situation. So, ultimately, the decision will come down to who brings them the best offer. So, who do you think will be the first Celtic to say goodbye?