Celtics trade Jrue Holiday to Portland for Anfernee Simons

Brad Stevens has made his first move this offseason with the mandate to get below the 2nd apron by trading Jrue Holiday back to the Portland Trail Blazers for guard Anfernee Simons and two 2nd round picks. The Celtics are saying at this point they plan to retain Simons, but are keeping their options open.

A league source said the Celtics acquired Anfernee Simons, who is on an expiring deal, because they like what he can bring to the roster, but added that they will "remain engaged on all fronts."

— Adam Himmelsbach (@AdamHimmelsbach) June 24, 2025

While Celtics fands are wishing Jrue Holiday nothing but the best as he was a key member in bringing home Banner 18, the NBA media is giving the Blazers a lot of credit for bringing in Holiday. Portlant traded Jrue to Boston two summers ago for Robert Williams, Malcolm Brogdon, and two first rounders.

The 26 year old Simons had fallen out of favor a bit in Portland, but has a strong offensive game. He will be on an expiring contract this coming season. The two second round picks Boston will also be acquriring are reportedly the 2030 Knicks and 2031 Blazers selections.

Good deal for both Portland and Boston, but the Celtics had the more urgent timeline, and get a certified bucket in the just-turned-26 year old Simons (if they keep him long term) to help make up for Tatum's loss.

— David Aldridge (@davidaldridgedc) June 24, 2025

Can’t wait to see what the Celtics do next. Do they flip Simons? Is it a simple Porzingis trade? Does someone make a monster offer for Brown or White? So many ways this could go…

— Kevin O'Connor (@KevinOConnorNBA) June 24, 2025