A summer of change is underway for the Boston Celtics. The 18-time NBA champions traded Jrue Holiday, a player pivotal to the most recent banner they raised to the TD Garden rafters.
Holiday heads to the Portland Trail Blazers, the team Boston acquired him from two years ago. In exchange, the Celtics will receive Anfernee Simons and a pair of second-round picks.
It's a move that signals Boston's intentions to retool during what may prove a gap year as Jayson Tatum recovers from his torn Achilles.
It also signals the Celtics' intentions of getting under the second apron. They don't need to do so until the end of the upcoming league year. However, while time is on their side, parting with Holiday is a step in that direction.
The consequences of being over the second apron in consecutive campaigns, coupled with the prospect of not having Tatum next season, make it prudent to get below that threshold.
In trading Holiday, Boston saves about $40 million in luxury tax payments in 2025-26. However, this move leaves the organization $18 million over the second apron. That's before factoring in salaries for draft picks and filling out the roster.
More moves to come for the Celtics
Simons is on an expiring $27.7 million contract. The 26-year-old guard would provide a needed infusion of speed and someone who will push the pace with the ball in his hands.
He's also a dynamic three-point threat. The six-foot-three guard ranked 13th among players averaging at least 3.5 pull-up attempts from behind the arc in the campaign that just concluded, per NBA.com. Simons made 34.7 percent of his 4.2 attempts on those. He's a skilled shooter coming off a screen as the ball handler. He can also effectively create long-range looks for himself.
The seven-year veteran also converted on 37.7 percent of his 4.3 catch-and-shoot 3s. It's a testament to him being a dynamic three-point shooter, which is where he adds the most value.
While Simons isn't much of a defender, he averaged 19.3 points last season and dished out 4.8 assists. He's grown accustomed to a high usage rate in recent years. That would require adjusting if he's on a team with Jaylen Brown, Derrick White, and Tatum.
Maybe the Celtics invest in him learning to play with that trio. However, as Adam Himmelsbach of The Boston Globe reports, while the Celtics are fans of what Simons brings to the table, they will "remain engaged on all fronts."
Getting under the second apron between now and the end of the upcoming league year is likely a goal of theirs. That means moving a hefty contract.
Simons now takes Holiday's place alongside Kristaps Porzingis as a prime trade candidate. The latter enters his age 30 season on an expiring deal worth $30.7 million.
Sam Hauser is another name to monitor. The six-foot-eight sharpshooter is only on Boston's books for slightly north of $10 million for the 2025-26 campaign. The problem is, even if they get under the second apron this offseason, the franchise would have to pay approximately $5.5 for every dollar spent at its repeater rate. That effectively puts Hauser's price tag at $55 million next season.
It's unfortunate to lose a player the organization helped develop into a productive two-way player and a rotation staple. However, it would make sense financially to target a team below the first apron who would use the $10.7 million taxpayer mid-level exception to absorb Hauser's salary.
What's clear is changes are coming. The Celtics did well, acquiring Simons, a skilled player who will help them retool, or he'll get rerouted as they aim to get under the second apron.
Receiving two second-round picks is also commendable. Pundits pondered if they would have to attach draft capital to move off Holiday's contract. The two-time All-Star is on the books for $32.4 million for the 2025-26 campaign. He has $104.4 million left on his deal. It lasts through 2027-28. The final year is a player option worth $37.2 million.
With its offseason reconstruction underway, those added assets could even go towards another deal between now and the draft's conclusion.