The Boston Celtics are trading veteran point guard Jrue Holiday to the Portland Trail Blazers in exchange for guard Anfernee Simons and two future second-round draft picks, according to sources who spoke to ESPN’s Shams Charania. The move is expected to save the Celtics $40 million in luxury tax payments during the 2025-26 season, according to ESPN’s Bobby Marks.

After Jrue Holiday helped the Milwaukee Bucks win the 2021 NBA Championship, he was traded to the Portland Trail Blazers in 2023 as part of a three-team deal that sent Damian Lillard to Milwaukee. Four days after being sent to Portland, he was traded to the Boston Celtics for Robert Williams III, Malcolm Brogdon, a 2024 first-round draft pick (which ended up being Bub Carrington), and a 2029 first-round draft pick.

Portland makes an aggressive move to re-acquire Holiday, who the franchise originally received from Milwaukee in the Damian Lillard trade in 2023 and later moved to Boston for a deal that included two first-round picks to Blazers. Simons joins Boston on an expiring contract. https://t.co/2TMs5Cd8qn

— Shams Charania (@ShamsCharania) June 24, 2025

During his time in Boston, Jrue Holiday became an integral part of the 2023-24 team that won the NBA Finals, averaging 13.2 points per game while making a career-high 42.9% of his three-pointers. He also earned All-Defensive honors in 2023 and 2024.

Anfernee Simons was taken with the 24th overall pick in the 2018 NBA Draft. Last season, he led the Portland Trail Blazers in scoring with 19.3 points per game in 70 starts.

A steal for the Celtics

Does Brad Stevens have some dirt on Trail Blazers general manager Joe Cronin? I ask because this is the second time in the last three years that the Celtics were able to get exactly what they wanted from Portland without having to give up any valuable assets.

Don’t get me wrong. Jrue Holiday is a good basketball player and an important veteran presence in any locker room. But Anfernee Simons is a 26-year-old shooting guard who just led an NBA team in scoring. If Portland had just sent Simons to Boston for Jrue Holiday, I would already consider that a win for the Celtics. But they also managed to acquire two second-round draft picks in the process?! What the hell is wrong with the Trail Blazers front office?

To most NBA fans, this looks like a salary dump. The Cs were prepared to pay Jrue Holiday $72 million combined during the 2026-27 and 2027-28 seasons. He was also in line to make $30 million this season, which would explain why Boston wanted to get rid of him. That part of the trade makes sense to me.

Anfernee Simons last two seasons:

— 20.6 PPG
— 5.1 APG
— 3.2 3PM

The newest Boston Celtic. pic.twitter.com/Gc8CgIFJP0

— StatMuse (@statmuse) June 24, 2025

Where I get confused is from Portland’s side of things. They’re doing the Celtics a favor by taking on Jrue Holiday’s contract. Even though Anfernee Simons is scheduled to be a free agent at the end of next season, it doesn’t make sense for them to move on from him when he just showed he can be the team’s leading scorer!

As a fan of an Eastern Conference NBA team, this type of stuff drives me crazy. The Celtics might have lost Jayson Tatum for the 2025-26 season, yet they still somehow managed to improve the supporting cast around him by landing an almost 20-point-per-game scorer. This is just further proof that Brad Stevens is one of the best in the business.

Will the Celtics pay Simons?

This is a very interesting move, regardless of how badly the Trail Blazers botched their side of the trade. Even though they were able to unload Jrue Holiday’s lofty contract, they are still deeply in the red in terms of cap space. According to Spotrac, the Celtics are 29th out of 30 teams in the NBA when it comes to cap space for the 2025-26 season (-$102.5 million). Therefore, the Cs probably aren’t done making trades and offloading salaries.

There are still plenty of guys in Boston making tens of millions of dollars next season. Kristaps Porzingis has a $30.7 million cap hit next year. Derrick White’s cap hit for the upcoming season will be $28.1 million. Al Horford, Sam Hauser, and Payton Pritchard have a combined cap hit of $35.3 million during the 2025-26 season. Add on Anfernee Simons, who has an almost $27.7 million cap hit, and it’s clear that the Celtics are still in financial trouble.

Here are the salaries going out

To Boston

Anfernee Simons: $25.9M, $27.7M (UFA, 2026)

* The Celtics get off the combined $72M owed to Holiday in 2026-27 and 2027-28

* Projected $40M in tax savings in 2025-26

* $18M over the 2nd apron

* Simons is extension eligible

To…

— Bobby Marks (@BobbyMarks42) June 24, 2025

Considering all the money they owe, I don’t see Boston signing Simons to any type of long-term extension unless they seriously change the complexion of the roster. Even then, it’s a long shot with Jayson Tatum and Jaylen Brown taking up almost 68% of the team’s cap space during the 2026-27 season.

There are two routes that I can honestly see the Celtics going with Simons. The first option will see them offload him in a trade that includes another highly-paid guy, so they can continue their salary-dumping process. The other choice Boston has is to just let Simons play this season on an expiring contract and then allow him to test out free agency. I think that will end up happening because I don’t know where the Celtics will get the money to pay Simons after this year. But if they somehow manage to extend him, then this trade looks even better for Boston and even worse for Portland.