The next trade Blazers must make after Jrue Holiday-Anfernee Simons swap with Celtics

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The next trade Blazers must make after Jrue Holiday-Anfernee Simons swap with Celtics

Matty Breisch · ClutchPoints

Wed, Jun 25, 2025 ·

4 min read

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The post The next trade Blazers must make after Jrue Holiday-Anfernee Simons swap with Celtics appeared first on ClutchPoints .

When news broke that the Portland Trail Blazers were re-acquiring Jrue Holiday in a trade with the Boston Celtics centered around Anfernee Simons , it took the NBA world by storm.

Suddenly, the 2024 NBA Champions were blowing up their core, with the Simons deal serving as an appetizer for the Kristaps Porzingis trade to come , and as a result, the very direction of the Eastern Conference has shifted for the foreseeable future.

But what about the Trail Blazers? Why was a team in the basement of the Western Conference looking to add a win-now player in Holiday and give up on a homegrown player in Simons, who is still only 26 years old? Well, while some of that has to do with Simons' fit with the Celtics' core, which is a bit redundant with younger scorers like Scoot Henderson and Shaedon Sharpe , it might also signify a change in the Blazers' plans moving forward, with the team looking to turn the page on their older core in favor of a young crop of emerging stars.

Could the Trail Blazers keep Holiday around to help Henderson and Sharp out both as a mentor and as a defensive backcourt player who knows how to win? Sure thing, but they would be wise to at least consider re-routing the 35-year-old guard, too , as they could potentially secure a quality return for his services that fits the team's long-term needs.

The Trail Blazers should re-route Jrue Holiday to Utah

The Celtics acquired Simons from Portland for one reason above all others: to save money.

Now granted, in some trades, it really can be a win-win for both sides, with one team looking for a guard and another after a big. But in this case, Simons was explicitly targeted not just because he could help to replace Jayson Tatum 's scoring pop but because he saved the team $20 million against the cap versus Holiday's figure, considering they were still over the second apron before the Porzingis trade.

Because the Celtics wanted to get off of that extra money, they were only able to get back Simons and two seconds for Holiday's services, which is less than the package , Malcolm Brogdon , Robert Williams , a 2024 1st round draft pick and a 2029 1st round draft pick, that they originally surrendered back in 2023. Granted, Holiday is two years older and is coming off a season where his numbers dipped a tad, but securing his services for less than a first-round pick is a fine piece of general managing from Portland's side of the deal.

But what would make it even better? Re-routing Holiday for a first-round pick and the requisite contract(s) the team would need to take back in order to make the deal kosher in the eyes of the NBA?

As things presently stand, the Trail Blazers are well under the first apron according to Spotrac, with the ability to still aggregate contracts even after the Holiday deal becomes official. Because they have an asset that almost every contending team in the NBA would like, and they can take on one or more contracts that maybe aren't the best from another NBA team and still have an ability to ask for a quality return from an asset standpoint.

Could a team like the Utah Jazz , who have a deep treasure trove of assets, look to add Holiday to their roster as they attempt to get where they want to be, aggregating the contracts of, say, Colin Sexton and John Collins for Holiday and Matisse Thybulle with Minnesota 's 21st overall first-round pick in this year's draft and a future second-round pick thrown to make it worth Portland's time? Would adding another young player just outside of the lottery be worth adding two more players with no long-term future on the team, who Portland could then trade again mid-season if a contender needs a combo forward or a combo guard to really take their offense over the top?

Considering that's exactly what the Trail Blazers did with Holiday the first time he landed in Portland, with Malcolm Brogdon already moved and "Timelord" still available for a center-needy team like the Los Angeles Lakers , who may have to pay a premium for his services, that feels like a resounding yes.

Normally, when a team makes a trade, it's a finished product. Celtics fans are watching various highlight videos of Simons as they prepare to see him suit up for the green and white this fall, and so are the Hawks faithful who just became the biggest Porzingis-heads in the NBA. But for Portland, Holiday's on-court debut isn't a lock just yet, as he very well could end up playing elsewhere before the end of the week, let alone the start of the regular season.

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