Celtics Get the Last Laugh as Jrue Holiday Trade Already Backfires in Portland
When the Boston Celtics moved Jrue Holiday to the Portland Trail Blazers this offseason, the deal looked like a win-win on paper. Boston offloaded a massive contract while Portland secured a championship-tested guard to help mentor their young roster. But in just a matter of months, the move has already backfired on the Blazers — and it leaves the Celtics looking like the smarter side of the transaction.
Why the Blazers Wanted Jrue Holiday
The idea in Portland was simple: bring in a respected veteran who could guide rising stars Scoot Henderson and Shaedon Sharpe. Holiday, fresh off helping Boston secure banner No. 18, fit the bill perfectly. He brought a defensive mindset, leadership, and championship experience that few players in the league can match.
But the plan didn’t survive the chaos of the offseason. When Milwaukee cut ties with Damian Lillard, Portland immediately scooped up their franchise legend, pairing him with Holiday in what quickly became a redundant backcourt. With two veteran guards on top of their developing stars, minutes and roles suddenly became murky.
Why Jrue Holiday Is Redundant in Portland
Holiday is still a valuable player, but he is no longer the same force he was in his prime. At 35, his best role is as a stabilizing presence, logging 25–30 minutes per game rather than carrying a heavy load. That makes sense for a contender — less so for a rebuilding team that just re-signed its franchise icon.
When Lillard returns from Achilles surgery, the Trail Blazers will have two aging veterans both expecting meaningful minutes, while also trying to give Henderson and Sharpe the developmental runway they need. Unless Portland commits to three-guard lineups on a regular basis, there’s a looming rotation squeeze.
And while Holiday may still “bleed green,” he’s now Portland’s highest-paid player, under contract through 2028. That makes him a likely trade candidate sooner rather than later.
Boston’s Side of the Deal
The Celtics, meanwhile, are dealing with their own complications after the trade. They’ve been looking to move Anfernee Simons in order to duck under the luxury tax, but so far, there haven’t been any takers. Instead, Boston plans to carry the 26-year-old into the season with hopes that strong early play could raise his value before the trade deadline.
Even if they can’t flip Simons right away, the financial relief from moving Holiday was substantial. Boston now has more breathing room as they try to maintain long-term flexibility around Jayson Tatum and Jaylen Brown.
Why the Celtics Won This Trade
The deal worked out almost perfectly for Boston. They shed Holiday’s expensive contract, gained a potential trade chip in Simons, and avoided the exact problem Portland now faces — paying top dollar to a veteran who no longer fits the timeline.
Meanwhile, the Blazers have essentially painted themselves into a corner. Lillard’s return ensures that Holiday won’t be the primary voice in the locker room for long. Portland will be stuck trying to balance minutes for two veteran guards while still prioritizing development for their young core.
Holiday can still help a team win, but not as the centerpiece of a rebuild. For Boston, watching Portland’s situation unravel is validation that they moved at the right time. Brad Stevens once again showed his knack for making tough calls before they became obvious to everyone else.
The Bottom Line
The Celtics wanted to get leaner financially without sacrificing their championship window, and they accomplished exactly that. Portland, on the other hand, wound up with a contract-heavy redundancy that could force their hand in the near future.
Jrue Holiday will always be respected in Boston, but his move westward already looks like a miscalculation. The Celtics, meanwhile, walk away with the last laugh — and potentially another win on the trade market if Simons boosts his value during the season.
