The breakup of the Celtics’ 2023-24 championship core was inevitable — it was a reality fans had been bracing for that finally came late Monday night when the Celtics shipped Jrue Holiday to the Portland Trail Blazers in exchange for Anfernee Simons and two second-round picks. The picks are the Knicks’ 2030 second-rounder, previously acquired by Portland, and Portland’s own 2031 second-round pick.
It’s the unfortunate reality of the league’s new CBA. The push for parity — with second-apron penalties and harsh financial restrictions — makes it nearly impossible to keep elite, expensive rosters intact. The Celtics, sitting roughly $20 million above the second apron with $227.8 million in projected salary across 12 players, entering Monday, had to make changes.
The Holiday trade is the first of many dominoes that are going to fall for the Celtics this offseason. Even after trading Holiday, the Celtics are still roughly $18 million over the second apron, and that’s before factoring in free agents.
Holiday still had roughly $104 million remaining on the contract extension he signed with Boston in the spring of 2024, including a $37.2 million player option for the 2027-28 season. By moving him, the Celtics clear a significant chunk of future salary from their books. Simons, meanwhile, arrives in Boston on an expiring $27.7 million deal for next season.
Given the Celtics’ need to cut costs — combined with the fact that Holiday just turned 35 and could be 36 by the time Jayson Tatum returns from his Achilles injury — he was always among the more likely trade candidates this summer.
Still, just because it was expected doesn’t make it any easier for Celtics fans. Holiday quickly became a fan favorite for his impact both on and off the court. And when it comes to what he did on the floor, his fingerprints are all over the 10-by-15-foot banner that will forever hang above the parquet. The Celtics’ 2024 championship wouldn’t have been possible without him.
Holiday’s impact was undeniable throughout the Celtics’ championship run, especially when the stakes were highest. In the Eastern Conference Finals, he made a strong case for MVP – averaging 18.5 points, 7.3 rebounds, and 5.8 assists – while delivering key moments like the game-sealing steal in Game 3 and the crucial offensive rebound in Game 4. His impact carried into the NBA Finals, where he averaged 14.4 points, 7.4 rebounds, and 3.8 assists, leading the team with 26 points in Game 22.
Fans will appreciate everything he brought to Boston for years to come, and he’ll surely get a warm reception every time he returns to TD Garden.
However, the Celtics face a delicate challenge: managing their salary cap predicament while avoiding a significant step back on the court. As difficult as it was to move on from Holiday, this trade helps accomplish that balance.
Jayson Tatum accounted for 26.8 points (23% of the team total), 20.3 shots (22% of the team total), and 6.0 assists (22.9% of the team total). The offense, obviously, is going to look much different with Tatum out, and Simons can help pick up some of the slack.
The Celtics are getting a dynamic playmaker and scorer in Simons, who averaged 19.3 points, 4.8 assists, and 2.7 rebounds in the 70 games (all starts) he played in Portland last season. He led the team in scoring a team-high 28 times and in assists a team-high 31 times.
He’s particularly a threat from three-point range, which bodes well for a Celtics team that set a new NBA record for made three-pointers — as well as a record for three-point attempts — last season. The 26-year-old, who has played seven professional seasons, all in Portland, is a career 38.1% three-point shooter. He has shot at least 36% in each of the last five seasons.
Last year, he made a career-high 215 three-pointers, making him one of just 20 players to make at least 200 threes. He shot 36.3% on 8.5 attempts per game, which would have ranked third on the Celtics last season behind just Tatum (10.5) and Derrick White (9.1). Furthermore, from the start of the new year through the end of the season, he averaged 3.4 made threes per game, the fifth most in the league during that span among players with at least 30 games played behind only Stephen Curry (4.6), Anthony Edwards (4.1), Malik Beasley (3.9), and White (3.5). He shot 38.2% over that stretch.
He’s made at least 200 threes in two of the last three seasons, joining Damian Lillard as the only players in Trail Blazers history with 200+ made threes in multiple seasons.
A former first-round pick (24th overall) in the 2018 NBA Draft, Simons — named after former NBA player Anfernee “Penny” Hardaway — has been viewed as a poor defender throughout his career. But he now joins a Celtics team that has finished second, second, and fourth in defensive rating over Joe Mazzulla’s three seasons as head coach.
For Boston to move Holiday’s contract, get a player who can contribute immediately, has the potential to fit the system beyond just this season, not have to attach any other assets, and still come away with two second-round picks — that’s a win.
With more moves to come, time will tell if Simons is flipped as Boston continues trying to escape the second apron. But as it stands now, this is a great return for a deal they (unfortunately) had to make.