Celtics-Blazers Deal for Jrue Holiday Will Be ‘Complicated’

Getty Jrue Holiday, Jayson Tatum

The Boston Celtics are in the mix for Jrue Holiday, according to a September 27 post on X by The Boston Globe’s Adam Himmelsbach. Holiday was sent to the Portland Trail Blazers that day as part of a deal that sent stars Damian Lillard from Portland to the Milwaukee Bucks and Deandre Ayton from the Phoenix Suns to Portland.

In assessing the Blazers’ next move with Holiday, The Athletic’s John Hollinger looked at three scenarios, including sending him to Boston.

“The Celtics can get to a salary match on Holiday, but it’s complicated,” Hollinger wrote in a September 28 story. “Malcolm Brogdon would be involved, but he makes $22 million in 2025-26, and that’s $22 million more than the Blazers want to take back. Additionally, the second contract in a Boston deal has to be either Robert Williams or Al Horford, which nukes the Celtics’ frontcourt depth … unless they make the salary match Brogdon, Payton Pritchard, Luke Kornet, Sam Hauser, Jordan Walsh and a signed-and-traded Blake Griffin instead. A six-for-one. Whew.”

Hollinger also suggested that the Trail Blazers might be hesitant to agree to trade Holiday to the Celtics, knowing the players they’d be getting back.

“The problem for Portland is, Boston is good and should be for many years with Jayson Tatum and Jaylen Brown still in their mid-20s,” he wrote. “The picks the Blazers would get would almost certainly be in the 20s. Ditto for that Warriors pick, too. It almost doesn’t matter the quantity because what are the odds of getting a lottery-level pick quality out of this?”

The Celtics may not have top-of-the-line draft assets to offer, but given that the Trail Blazers have every intention to trade Holiday ASAP, according to ESPN’s Adrian Wojnarowski, they may not have necessarily better options from other suitors.

Celtics Among Teams Jrue Holiday’s Interested In: Report

According to Anthony Chiang and Barry Jackson of the Miami Herald, the Celtics are among the multiple teams that Holiday would have interest in playing for.

“League sources told the Miami Herald on Thursday that the [Miami] Heat, Los Angeles Clippers, Los Angeles Lakers, Boston Celtics, Chicago Bulls, and Philadelphia 76ers are destinations that appeal to Holiday,” Chiang and Jackson wrote in a September 28 story.

The commonality among those teams is that they are all in positions to contend for a title, though some are in a better place than others, even without Holiday onboard.

Celtics Not Expected to Acquire Holiday: Insider

Despite there being some level of mutual interest between the Celtics and Holiday, MassLive’s Brian Robb reported that it’s more likely than not that the Celtics will lose the bidding war for the two-time star.

“Several reports have linked the Celtics as likely bidders for the defensive-minded guard. However, multiple league sources told MassLive they do not expect Boston to come out on top in what is guaranteed to be a competitive bidding war among contenders in both conferences,” Robb wrote in a September 28 story.

Despite there being interest, the Celtics currently aren’t desperate the way their roster is constructed. Their guard rotation is Derrick White, Malcolm Brogdon, and Payton Pritchard, which is pretty solid, even if Holiday would give them an upgrade. However, the Celtics may have to wonder how concerned they should be if Holiday ends up in the hands of the Heat or Sixers.