Grade The Trade: Who Won The Jrue Holiday For Anfernee Simons Swap?

The Boston Celtics’ blockbuster move is exactly what they wanted: trading 35-year-old Jrue Holiday to the Portland Trail Blazers in exchange for 26-year-old scoring guard Anfernee Simons and two future second‑round picks. Boston’s rationale is clear: a move driven by financial obligations. 

Trade Details

Boston Celtics Receive: Anfernee Simons, two second-round picks

Portland Trail Blazers Receive: Jrue Holiday

Jrue Holiday, a two-time NBA champion and perennial defensive stalwart, carries three seasons and over $100 million remaining on his deal. By swapping him, the Celtics clear roughly $40 million in luxury tax obligations. 

In return, Boston acquires Simons, a high-octane scorer with a 19.3 PPG average this past season and one year left on a modest $27.7 million salary, plus two second-round selections. That’s a win-now asset who aligns with their potent 3-point offense and a pair of future draft chips.

For the Trail Blazers, the catch is more strategic. Re-acquiring Holiday brings championship pedigree, elite defense, and veteran mentorship to a young, ascending core led by Scoot Henderson and Sharpe. 

This trade is more than a simple player swap. Boston cashes in cap flexibility and long-term upside. Portland bets on experience and identity. But which franchise truly gained the upper hand? We have an idea.

Boston Celtics: A

Boston’s front office hit the jackpot in this trade. They secured much-needed luxury-tax relief and added a dynamic 20+ PPG scorer in Anfernee Simons, a perfect fit to temporarily offset Tatum’s absence. 

Swapping Holiday’s $67M+ outgoing contract for Simons’ expiring deal and saving roughly $40M in tax penalties resets their cap situation and gives them room to pivot this summer. The two second-round picks are cherries on top, offering future flexibility or move-making chips.

Simons averaged 19.3 PPG last season and arrives with scoring at all three levels, exactly what Boston will need as Tatum rehabilitates. His youth and shot-making potential give the Celtics both immediate impact and roster depth, while only adding a one-year salary commitment. That’s a textbook A-grade return in both financial and on-court terms.

Portland Trail Blazers: C

From Portland’s standpoint, this trade feels like a veteran reclamation project without clear upside. Jrue Holiday brings championship DNA and elite perimeter defense to a young roster, a potential mentoring asset. 

Yet, at 35 years old and locked in for two more heavy years, his contract sits at $67M, and it cost them Simons plus two future second-rounders. The grade could climb if Portland turns Holiday into better assets midseason, but as it stands, this feels like a gamble on age and chemistry rather than long-term build. 

Jrue Holiday: D

Holiday leaves Boston, a contender with a championship pedigree, for a limbo situation in Portland. He’s now on a rebuilding team with uncertainty surrounding roster construction and playoff outlook. 

While he likely maintains a starting role (unless he is moved again) and potentially helps vet young guards, this move marks a clear step back from contention. There’s still respect for his defensive impact and leadership, but at this stage of his career, he’s forfeiting peak opportunities for a long-term, burdensome contract.

Brad Stevens: A+

Is there anything this guy can’t pull off? Stevens once again navigated the luxury tax minefield, shed $40M in penalties, and caught Simons at the perfect time with minimal cap disruption, all while improving the roster. It’s another masterclass in asset management and roster orchestration, the kind that earned him Executive of the Year credentials last season.

How does he keep doing this? His unique blend of college scouting connections, financial acuity, and willingness to take calculated risks keeps yielding wins. If there’s a loophole in the CBA, you can bet Stevens has found it.

Anfernee Simons: B+

This is a golden opportunity for Simons. He steps into a meaningful role on a contenders-adjacent team, gets to showcase his shot-making in pressure scenarios, and arrives expiring, making him extension-eligible after a strong season.

However, his defensive limitations are no secret. To elevate to the next level in Boston’s structured system, he’ll need to significantly improve on-ball defense and effort. If he can, this could be the make-or-break moment that turns him into a reliable two-way starter, not just a scorer.