BOSTON – The Boston Celtics just made the first of what will likely be several cost-cutting moves. The Celtics traded 2024-25 champion Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two second-round picks. Brad Stevens took another swing at the fences with this deal. More details will emerge, but so far it looks like a home run.
Anfernee Simons To The Celtics: Trade Grades And Cap Implications
Holiday joined the Celtics via a three-team trade with the Trail Blazers and Suns. The Blazers acquired him from Milwaukee, then quickly moved him to Boston. He spent two successful years in Boston, helping the team win 80 combined regular season and playoff games en route to Banner 18.
In Milwaukee, he served as the second scoring option. In Boston, he embraced the role of fourth option. Holiday sacrificed for team success. But with Jayson Tatum sidelined for the season with a torn Achilles, the Celtics had to change direction and cut costs.
Brad Stevens Pulls Another Smart Move
Stevens built this championship roster with smart trades for Holiday and Kristaps Porziņģis. Now, he’s retooling under pressure. The Celtics were on pace to reach a half-billion payroll. Trading Holiday saved them $4.1 million in cap space and about $40 million in tax payments.
Once Holiday signed an extension in April last year, the writing was on the wall. Keeping this team together under the new CBA wasn’t realistic. Tatum’s injury accelerated a decision the front office likely would’ve made anyway.
This trade also lands the Celtics a potential gem in Anfernee Simons. Simons flew under the radar in Portland due to mediocre team results and the post-Lillard rebuild. He averaged over 20 points and shot 38.1% from three the past three seasons.
Simons adds scoring and fits Mazzulla’s three-heavy system. His contract expires soon, giving Boston flexibility. His defense struggled in Portland, but his 6’9″ wingspan suggests he could improve.
Team sources say the Celtics originally asked for a first-rounder and salary filler. This package isn’t that, but might be even better.
Grade: A
Financial Implications for the Celtics
Boston also acquired two second-round picks, useful in future trades. The Celtics still own all but one of their future first-rounders, including pick No. 28 in this draft. The exception is a 2029 pick owed to either Portland or Washington.
The trade clears $72 million in future commitments to Holiday. Still, the Celtics remain $18 million above the second apron. More moves are coming as they try to get under the hard cap.
Trail Blazers’ Motives Aren’t Clear
Portland’s decision to trade Simons and two second-rounders for a 35-year-old Holiday is puzzling. Holiday will earn $32.4 million in 2025-26 and could pick up a $37.2 million option for 2027.
On the bright side, Holiday brings defense and leadership. He could help young guards like Scoot Henderson, Shaedon Sharpe, and rookie Donovan Clingan. Henderson, especially, could benefit from his mentorship.
The front office may not have seen Simons as part of their long-term plans. He’s in a contract year. Portland may have doubted his long term fit or willingness to extend. They may also want to free up minutes for Sharpe.
But giving up Simons and picks to take on Holiday’s salary feels aggressive. If Holiday stays healthy—despite missing 63 games in four years—this might work. Otherwise, it could backfire.
Grade: C
Cap Implications for the Trail Blazers
Portland lost two second-round picks, which likely won’t matter long-term. They still own all their future firsts, except the 2026 pick owed to Chicago. They also hold swap rights with Milwaukee in 2028 and 2030.
If they pick up team options on players like Henderson, Sharpe, and Rayan Rupert, they’ll have 13 players under contract.
Notable free agents include Dalano Banton (unrestricted) and Jabari Walker (restricted). The team sits just $3 million under the second apron. Extensions for Sharpe, Rupert, Toumani Camara (an All-Defensive Second Team selection this year), and Matisse Thybulle could push them well over.
This is a heavy payroll for a team that won only 36 games this season. Maybe this move gets them into the play-in, but at what long-term cost?
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