The surprising Anfernee Simons-Jrue Holiday deal between the Portland Trail Blazers and Boston Celtics has been made official. The Blazers announced in a press release that the finalized deal will be a straight one-for-one player swap without the two second-round picks that were previously reported to be heading over from Portland to Boston.
Even without those picks attached, this trade is still a lopsided win for the Celtics.
The Boston Celtics officially won this trade
In a vacuum, Holiday is a much more talented and impactful player than Simons. Compare the two resumes, and it's easy to see why Holiday -- a two-time NBA champion, two-time All-Star, six-time All-Defense, and two-time Olympic gold medalist -- comes out on top. But context is everything in these rare one-for-one trades.
The entire point of a trade is to improve your team's outlook, whatever that may be for your respective situation. For Boston, it was clear that their goal this offseason was to shed salaries, especially after Jayson Tatum's brutal Achilles tear. They accomplished just that with this deal, offloading Holiday's three-year, $104 million contract (arguably one of the worst in the league) for Simons' expiring $27.7 million salary.
The Celtics now have much-needed flexibility. They could look to flip Simons, a much easier piece to move. Alternatively, they could even use this time without Tatum as a gap year or audition for Simons, seeing if it justifies an extension. It's easy to see a path where Simons thrives in Joe Mazzulla's style of offense as Boston led the league in three-point attempts (48.2 per game) by a wide margin.
The Blazers' reasoning for this trade doesn't add up
The reasoning behind the trade from the Blazers' standpoint is that Holiday fits much better with the defensive-minded identity that Joe Cronin and Chauncey Billups have been building. This move was a bet on the Blazers' young core after a promising finish to the 2024-25 season; however, this mindset has glaring flaws.
The entire point of trading Simons was to give Scoot Henderson the immediate keys to the backcourt and get an asset in return for Simons, rather than simply letting him walk next summer because Portland shouldn't overpay to extend. Now, they find themselves in a similar predicament with Holiday.
He's a declining player whose contract will only get harder to justify. And although it's possible Billups elects to start Henderson over Holiday, it's hard to envision that's what they had in mind when making this aggresive deal.
This type of swap would make much more sense had Portland been ready to contend and were one upgrade away from making serious playoff noise. But we hardly know if this swap is enough to get them back in the postseason, making the trade for a 35-year-old guard much more confusing.
At least the Blazers didn't have to include two second-round picks to make it even more lopsided. However, Boston was still the clear winner, given both teams' respective situations and reasons for this trade.