Winners and Losers from Celtics' and Blazers' Jrue Holiday and Anfernee Simons Trade
This NBA offseason isn't waiting around for the draft to get rolling. Heck, the Kevin Durant trade went down before the Finals even ended. And one day after Game 7, ESPN's Shams Charania broke the news that the Boston Celtics were dealing Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two second-round picks.
After Jayson Tatum ruptured his Achilles in the playoffs, money-saving moves felt inevitable for Boston. It would've been hard to justify a payroll over the second apron without a chance of competing for the title. And this particular deal saves the Celtics a fortune (more on that later).
It's also not likely to be their only cost-cutting move of the summer. Charania added that Boston is "engaged in trade talks surrounding multiple key players on the roster..."
We'll have plenty of time to dissect those moves if and when they materialize. For now, it's time for a closer look at the Holiday deal that also landed Anfernee Simons in Boston.
Winner: Anfernee Simons
1 of 5
This move is a pretty clear signal that the Celtics are angling toward a gap year while Tatum recovers. That means Simons could be going from the up-and-coming Blazers to a team in purgatory. And when his contract expires in 2026, he could be out. The flexibility is obviously part of why Boston acquired him.
If you focus on that, you might be able to sell Simons as one of the "losers" here, but there's a more optimistic view of his new situation.
On a team without Tatum and now in the weaker conference, Simons has a chance to really showcase his scoring ability in a contract year. And while you could argue he's essentially been in that situation for two years, the Celtics are indisputably a higher-profile organization.
If Simons—who's averaged 19.9 points, 4.5 assists and 3.2 threes, while shooting 38.1 percent from deep over the last four seasons—has some huge games on national television, he could raise his own profile a bit ahead of free agency.
And if he buys into Boston's culture, the next team to sign him might just be the Celtics. In that case, Simons could be on a rebuilt contender for Tatum's return in 2026-27.
Loser (Kind Of): Jrue Holiday
2 of 5
Holiday is on the opposite end of the equation, leaving a team that looks intent on shedding salary this summer and going to one that should compete for a play-in spot in the brutal West.
Being the veteran leader there is a role Holiday will surely embrace. Given his approach to his entire career, you can be sure he'll treat the situation like he's a winner.
But Holiday is also a two-time champion who was salary-dumped by the teams he helped push over the finish line shortly after pushing. Both times.
There's also some hint of indignity in simply being a cap casualty, which is exactly what Holiday is.
Finally, though Portland is certainly headed in the right direction, they're doing it in the West. When Holiday signed his last extension in Boston, he had to think he'd be on a title contender for the next half decade.
The Blazers almost certainly aren't going to be that.
Winner: Celtics
3 of 5
As soon as Tatum went down in the second round against the New York Knicks, Boston shedding salary almost felt like a foregone conclusion. This is probably just the first domino.
That it brought more than just savings when it fell is a real bonus.
In this deal, Boston gets an extended audition from Simons, a playmaker who's almost a decade younger than Holiday and two second-round picks.
And while that second part of it may not sound like much, it's better than the alternative for a lot of teams looking to unload players in their mid-30s.
Holiday is 35 and under contract through 2027-28, when he has a $37.2 million player option. Some suitors may well have demanded that Boston include sweeteners to take that on.
Loser: Celtics Fans
4 of 5
Ultimately, this is a good move for the Celtics. And the fan base will certainly survive a single down year while they wait for Tatum to return.
But this trade and each subsequent one that materializes this summer (assuming they do), will be not-so-subtle reminders of how fragile contention is in the current NBA.
When Boston won the title in 2024, their entire roster was locked in for the foreseeable future. Their two best players were both in their 20s. It felt like the team would perennially be in the hunt for titles.
Now, for at least a year, the Celtics and their fans will have to support a team unlikely to contend.
Winner (For Now): Trail Blazers
5 of 5
There's some potential pain down the road for the Blazers on this deal. Assuming Holiday picks up the aforementioned option, he'll be 38 when this contract ends. If he doesn't push the team back to the playoffs or make it meaningfully better, there could be some griping over his contract. It could also get tougher to trade as he ages.
But this is a short-term win for a young team that made some noise down the stretch last season (they went 18-11 in a stretch from mid-January to mid-March).
Portland has a dynamite defensive duo at the forward spots in Deni Avdija and Toumani Camara. The former looked like a bona fide point forward by the end of the year. There's still plenty of untapped potential from Shaedon Sharpe and Scoot Henderson. And after Deandre Ayton went down for the season, Donovan Clingan started to look like a bona fide defensive anchor.
Adding Holiday's leadership, championship experience and spot-up shooting could very well push the Blazers back to the playoffs (or at least the play-in).
