Boston Celtics Acquire Anfernee Simons from Portland Trail Blazers for Jrue Holiday

Photo credit: Ronald Martinez, 2023 Getty Images.

Another big trade hit the NBA world late Monday night into early Tuesday as the Boston Celtics traded guard Jrue Holiday to the Portland Trail Blazers for combo guard Anfernee Simons and two second-round picks. The picks are a Knicks’ 2030 pick and a Blazers’ 2031 pick, according to Bleacher Report’s Jake L. Fischer. The trade was first reported by ESPN’s Shams Charania. 

Holiday had been a key member to the Celtics over the past two seasons, averaging 12.5 points and 11.1 points and playing in 131 regular season games. More important than his averages though was his impact on the Celtics’ perimeter defense. His experience was needed and he provided that as he and Derrick White formed the league’s best defensive backcourt. It all paid off in 2024 in the form of the franchise’s 18th NBA championship. 

Initially traded to the Blazers on September 27, 2023 in the deal that sent Damian Lillard to the Milwaukee Bucks, Holiday is now going to Portland where he joins a young and talented group that includes Scoot Henderson (21), Shaedon Sharpe (22), Toumani Camara (25), Delano Banton (25), and Donovan Clingan (21). Camara made 2nd team All-Defense in 2025, Sharpe has defensive ability and Clingan is a shot-blocking presence inside. Defensive wing Matisse Thybulle, it was announced on Tuesday via Chris Haynes, is opting into his $11.5 million player option for 2025-26. The Blazers will have strong defense on the wings. If Holiday and the Blazers want, Holiday can be a valuable veteran piece and add to the defense of a group that came out of nowhere to have a strong 2025 (36-46 overall record, three games back of 10th). From January 19 through to February 6, the Blazers won eleven of twelve games, they won four straight from February 22 to 28, and four straight from March 16 to March 21. Holiday is due $32.4 million for the upcoming season and $34.8 million in 2026-27 before a player option in 2027-28 of $37.2 million when he will be 37 years old. The trade saves the Celtics $40 million in tax. 

Simons, meanwhile, made $25.9 million in 2024-25 and will make $27.7 million in 2025-26. At the end of next season, he will be an unrestricted free agent. 

In 2022-23 and 2023-24, the 6 foot 3 inch, 26-year-old averaged 21.1 points and 22.6 points per game. This past season, he averaged 19.3 points in seventy games on 42.6% shooting. Simons is a fluid scorer whose presence along with Henderson and Sharpe provided the team with scorers but at the same time gave head coach Chauncey Billups an overabundance of guards. Trading away Simons solves that issue for the Blazers. One of the reasons that you would think that Holiday would be bought out would be to give Henderson the opportunity to start at point guard for the first time in his career and build on the team’s youth moving forward. 

From the Celtics’ vantage point, Holiday was commanding a lot of money and White essentially does the same things but is four years younger, so it was not a necessity to keep Holiday. With Jayson Tatum’s Achilles injury keeping him out for a large portion of next season, Simons can slide into the starting lineup, and he gives the Celtics a bonafide scorer in the absence of Tatum. This move allows the Celtics to get a jumpstart on teams like the Indiana Pacers and Milwaukee Bucks who next season will also have stars out (Tyrese Haliburton, Damian Lillard) with Achilles injuries. 

Other NBA News: Daniel Gafford resigns with Dallas Mavericks 

On Monday, center Daniel Gafford re-signed with the Dallas Mavericks for $54 million over three years. The terms were reported by Marc Stein. 

Gafford, 26, averaged 12.3 points and 6.8 rebounds in 57 games in 2024-25. He is a solid rebounder, blocks shots, and is a lob threat. He is one third of a big man trio in Dallas that includes superstar Anthony Davis and 21-year-old Dereck Lively II. 

The Mavericks, who hold the No. 1 overall pick in Wednesday’s draft, will have Cooper Flagg in the fold next season. Gafford was one key player to bring back for the organization’s 2025-26 plans and beyond.