Sachin Shankar Yadav By acquiring Anfernee Simons from the Portland Trail Blazers in return for Jrue Holiday and two future second-round draft picks, the Boston Celtics have made a big move. With Boston looking to retool its roster after a disappointing playoff exit and the injury to star forward Jayson Tatum, this trade represents a significant shift for both teams.
Trade Analysis: Boston Celtics Acquire:
- Anfernee Simons (SG/PG, contract expiring, 1 year, $27.7 million)
- 2030 second-round selection of the New York Knicks
- 2031 Portland Trail Blazers second-round selection
The Portland Trailblazers are given:
- Jrue Holiday (PG/SG, 3 years, $104.4 million left)
The Reasons Behind the Celtics’ Decision
- Financial Flexibility: The Celtics are subject to severe second-apron and luxury tax restrictions. Boston moves below the second apron by saving roughly $5 million on the books and an estimated $40 million in luxury tax payments next season by trading Holiday, who is owed over $100 million, for Simons’ expiring $27.7 million contract.
- Roster Transition: Boston is moving toward a more offensively focused roster as Jayson Tatum is probably going to miss the majority of the upcoming season due to a torn Achilles. A number of offseason moves to manage the payroll and reshape the team may begin with this trade.
- Offensive Boost: Simons averaged 19.3 points, 4.8 assists, and 2.7 rebounds in the previous season, demonstrating his prolific shooting and scoring abilities. His three-point shooting is well-known. (career 38.1% from deep, 37.4% during the last three years), which aligns nicely with the offensive philosophy of coach Joe Mazzulla. Additionally, he made more than 200 three-pointers in two of the previous three seasons, including a career-high 215 in 2024–2025.
- What Simons Brings to Boston: Simons is a prolific, effective three-point shooter who can also create his own shot. Over the past four seasons, he averaged almost 20 points per game and established himself as a dependable offensive weapon.
- Contract Situation: Simons is a possible extension candidate because his current contract is about to expire, but the Celtics are probably going to wait and see how well he fits before committing to a long-term deal.
- Defensive Limitations: Simons is a highly skilled offensive player, but his defense is a well-known flaw. He is frequently singled out by opponents, so Boston will need to plan to make up for his defensive deficiencies, particularly with Tatum out.
What Will Happen to the Celtics Next?
- Future Plans: The Celtics are hoping to get completely under the second apron and retool for the future, so this trade is probably the first of many to come.
- Short-Term Outlook: Without Holiday, Boston’s defense may regress, but Simons will help cover the scoring gap created by Tatum’s injury.
- Long-Term Decisions: Before contemplating a contract extension, the Celtics will assess Simons’ suitability. His contract is about to expire, giving him flexibility for future moves.
As the Celtics navigate a difficult offseason, Anfernee Simons’ arrival ushers in a new era that combines financial strategy with the need for offensive firepower.