Dec 12, 2024; Boston, Massachusetts, USA; Boston Celtics guard Jrue Holiday (4) waits for game action to resume during the first half against the Detroit Pistons at TD Garden. Mandatory Credit: Eric Canha-Imagn Images Eric Canha-Imagn Images

Recently Traded $134 Million Guard Gets Important Update On Future

Originally posted on Detroit Pistons on SI
By Justin Grasso | Last updated Jun 25, 2025 7:07 PM ET

Although it wasn’t a popular opinion in Detroit, the Pistons were suggested to pursue former Boston Celtics guard Jrue Holiday on multiple occasions throughout the offseason.

As expected, the Celtics dealt Holiday away. The veteran guard is set to join the Portland Trail Blazers.

Funny enough, that’s not the first time Holiday was sent to the Blazers. Before he made it to Boston, the Milwaukee Bucks moved Holiday to the Blazers in the blockbuster that sent Damian Lillard to a new team for the first time in his career.

Once Holiday landed on the Blazers’ roster, Portland was expected to continue shopping his name around. It didn’t take long before the Celtics sent Robert Williams, Malcolm Brogdon, and multiple first-round picks out West to acquire Holiday.

For the second time in his career, Jrue Holiday won a championship with the Celtics. The two-way standout’s value was clear throughout the year and into the postseason.

While the Celtics likely weren’t eager to part ways with Holiday after two seasons, their cap sheet left them no choice but to make some tough decisions. The Celtics moved Holiday to the Blazers, which opened up another can of questions regarding the guard’s future. Once again, will Holiday be moved?

This time around, it seems doubtful. Although there have been rumblings suggesting that Holiday is displeased with his trade destination, the NBA Insider Jake Fischer has reported that the Blazers aren’t interested in flipping Holiday.

“There was interest in Jrue Holiday from Sacramento, Dallas and others. The plan, for now, is definitely for Portland to keep the veteran point guard, sources say, as the Blazers look to compete in the Western Conference,” Fischer wrote on X. “I’ve seen some wondering whether or not POR would flip him.”

There was interest in Jrue Holiday from Sacramento, Dallas and others. The plan, for now, is definitely for Portland to keep the veteran point guard, sources say, as the Blazers look to compete in the Western Conference. I've seen some wondering whether or not POR would flip him. https://t.co/uKR3pp01Ww
— Jake Fischer (@JakeLFischer) June 24, 2025

Even if Holiday became available again, his fit with the Pistons would be questionable. The veteran guard’s primary position has been listed at point guard since 2020. There’s no reason to take the ball out of Cade Cunningham’s hands.

Holiday as a backup point guard would be interesting, but that’s an expensive situation. Not only would it cost assets to land Holiday initially, but then he would be owed over $100 million over the next three seasons. That kind of cost goes against Trajan Langdon’s current thinking.