On Monday, the Portland Trail Blazers traded promising guard Anfernee Simons to the Boston Celtics in exchange for veteran point guard Jrue Holiday, according to reports from ESPN’s Shams Charania. Along with Simons, Portland included two second-round draft picks in the deal.
This transaction marks a significant shift in both teams’ rosters as they prepare for the upcoming seasons. The Trail Blazers bring in Holiday to provide experienced leadership, while the Celtics add a young scorer in Simons to deepen their backcourt.
Financial and Salary Cap Implications of the Trade
ESPN analyst Bobby Marks explained that Portland will take on Holiday’s remaining contract obligations, which total approximately $72 million over the 2026-27 and 2027-28 seasons. For the Celtics, this trade results in $40 million in tax savings for the current season but pushes them $18 million above the NBA’s second luxury tax apron. According to Spotrac data, Boston was already $58.5 million over the salary cap before this move.
Before the trade, Portland was $36.26 million over the salary cap but remained comfortably under the apron limits, sitting $9.49 million under the first apron and $20.29 million below the second. This strategic maneuvering by both teams reflects ongoing efforts to manage their financial flexibility while reshaping their rosters.
Detailed Roster Updates for Both Teams
The Celtics’ updated roster for the 2025-26 season now features guards Anfernee Simons, Payton Pritchard, and JD Davidson at the point guard position. Their shooting guard group includes Derrick White, Baylor Scheierman, and Jaden Springer, while forwards Jaylen Brown and Torrey Craig anchor the small forward spot. The power forward rotation is led by Jayson Tatum, supported by Sam Hauser, Jordan Walsh, Drew Peterson, and Miles Norris. In the center position, Boston fields Al Horford, Luke Kornet, Kristaps Porziņģis, Neemias Queta, and Xavier Tillman.
Meanwhile, the Blazers’ roster now contains Jrue Holiday, Scoot Henderson, and Dalano Banton as point guards. Their shooting guards include Shaedon Sharpe, Rayan Rupert, Matisse Thybulle, Bryce McGowens, and Taze Moore. Small forward duties are shared by Deni Avdija, Kris Murray, Jabari Walker, Justin Minaya, and Sidy Cissoko. Power forwards Toumani Camara and Jerami Grant complement this group, while the center position features Donovan Clingan, Deandre Ayton, Duop Reath, and Robert Williams.
Anfernee Simons Finds New Opportunity with Celtics
Simons has expressed that he did not feel the need to request a trade despite the Blazers’ struggles last season. Speaking to Jason Quick of The Athletic, Simons said he lacked
“the cachet or urgency to demand a trade.”
Although Portland ended the previous campaign with a 36-46 record, finishing 12th in the Western Conference, Simons remained patient throughout. Oregonian’s Aaron Fentress described the offseason uncertainty as “a toss-up” regarding whether Simons would be moved.
The Celtics face a potential down year as star Jayson Tatum recovers from a torn Achilles, which could present Simons with a prime opportunity to establish himself in Boston’s rotation alongside Jaylen Brown and other key players. Despite the temporary setback, the Celtics remain positioned to contend for a playoff spot.
Blazers’ Transition After Damian Lillard Era
This trade is a continuation of Portland’s rebuild since trading franchise icon Damian Lillard to the Milwaukee Bucks before the 2023-24 season. Initially, Simons appeared to be a cornerstone for the Blazers’ future alongside 2023 third overall pick Scoot Henderson. However, the franchise ultimately decided to part with Simons in favor of securing an experienced veteran like Holiday to guide their young squad.
Simons signed a four-year, $100 million contract three years ago and will earn $27.7 million in the 2025-26 season, the final year of his deal. Last season, he participated in 70 games, posting a team-high average of 19.3 points per game along with 2.7 rebounds and 4.8 assists. This was the first time since the 2021-22 campaign that his scoring dipped below 20 points per game.
Simons’ Development and Background
Before his professional breakthrough, Simons followed an unconventional path to the NBA. After graduating high school in 2017, he spent an additional year at IMG Academy. Rated as a five-star recruit following his reclassification to the 2018 class, Simons de-committed from Louisville amid the school’s federal investigation for fraud, choosing instead to enter the 2018 NBA Draft straight from high school. The Blazers selected him with the 24th overall pick.
After initial seasons of steady growth, Simons made a significant leap in 2021-22, averaging 17.3 points across 57 games. He continued to improve, achieving career-best averages last season in 46 games, with 22.6 points, 5.5 assists, and 3.6 rebounds while shooting 43 percent from the field and nearly 39 percent from beyond the arc.
What Jrue Holiday Brings to Portland
At 33 years old, Holiday enters the Blazers’ roster as a seasoned leader ready to help nurture a young core. His veteran experience is expected to anchor Portland’s backcourt and provide stability during a transitional phase for the team. With key players like Henderson and Sharpe, Holiday’s presence could help accelerate the development of Portland’s promising talent as they aim to improve their standing in the Western Conference.