The 2025 NBA offseason has barely begun and we already have two trades involving former All-Stars. On Sunday, the Houston Rockets won the Kevin Durant sweepstakes, and now, Jrue Holiday is en route to the Portland Trail Blazers.
BREAKING: The Boston Celtics have traded Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two second-round picks, sources tell ESPN. pic.twitter.com/2ycXQicGkT
— Shams Charania (@ShamsCharania) June 24, 2025
To commemorate this occasion, I figured it was wise to grade the transaction from both the Blazers and Boston Celtics’ perspectives.
Boston Celtics
Heading into the summer, the Celtics had two main goals. First, they needed to cut salary to avoid the financial penalties of being over the second apron. Secondly, they needed cut costs in a way that still gives them a chance to be competitive in 2026-27, presumably when Jayson Tatum will be back in action.
This trade accomplishes both of those objectives. By trading Holiday, the Celtics shaved $4.7 million off their payroll and a whopping $41 million from their projected tax penalty, as outlined by cap expert Yossi Gozlan.
The Boston Celtics only reduce their payroll by $4.7 million by going from Jrue Holiday to Anfernee Simons but decrease their tax penalty by $41 million.
$46 million in total savings while factoring in a salary for the 32nd pick.
Still deep above the second apron. pic.twitter.com/9W2sbd0qUm
— Yossi Gozlan (@YossiGozlan) June 24, 2025
The best part is the Celtics got off Holiday’s monstrous contract (three years, $104.4 million remaining) without having to attach any draft capital. Not only did they get off Holiday’s contract scot-free, they acquired positive assets in return via Anfernee Simons and two second-round picks.
Speaking of Simons, there are many ways the Celtics can handle him. Since he’s on an expiring deal, the Celtics could seek to re-route him to a playoff team looking for a spark-plug scorer. They could also use him as a one-year rental to help fill the shooting and on-ball creation voids left by Tatum. Or, they could keep him and look to re-sign Simons to a long-term deal, making him part of the next great Celtics team when Tatum returns. At the end of the day, I can’t think of a better outcome for Boston.
Grade: A+
Portland Trail Blazers
At first, I didn’t really like this trade for the Blazers. Yes, Holiday makes an already formidable defense (fourth in defensive rating after the All-Star Break) even more impenetrable. But trading your best shooter/spacer and second-best initiator (I’d say Deni Avdija is still better in this area) for an aging star who’s experienced a significant dip in scoring volume/aggression over the last couple of years does not help your offense. That was this team’s real area of weakness, ranking 20th in offensive rating after the All-Star Break and 22nd overall.
On top of that, how are you giving the Celtics draft picks when they’re the ones asking you to do them a favor and save them some money?
However, Yahoo Sports’ Kevin O’Connor offered a perspective I hadn’t thought of, which has loosened me up to this decision from Portland. For those who haven’t seen his tweet, here’s a quick summary.
Like I mentioned above, Holiday makes an already sick defense even more nasty. The Oklahoma City Thunder just taught us defense wins championships, and the Blazers certainly have a surplus of that now.
Holiday is also a battle-tested veteran with championship pedigree and the ability to serve as a mentor to inexperienced youngsters — of which the Blazers have plenty (they were the third-youngest team in the league last year). He can help build a winning culture before the final year of his deal, when Portland could choose to use him as matching salary (he’s owed $37.2 million in 2027-28) in a trade for a star player at the peak of their powers.
