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Before Jrue Holiday was traded to the Boston Celtics in 2023, they didn't have a single player on the active roster with an NBA title to their name. Holiday changed that with his championship pedigree, which proved contagious, as the Celtics roster is full of rings following a commanding series victory in the 2024 NBA Finals. The two-time champ will now look to bring his winning ways elsewhere after being traded to the Portland Trail Blazers for guard Anfernee Simons and a pair of second-round picks.
Late on Monday night, ESPN insider Shams Charania announced that the C's had dealt Holiday back to the Trail Blazers. Even though the 35-year-old has never played a single game for the Blazers, he was briefly with Portland in the summer of 2023 after being moved by the Milwaukee Bucks in their pursuit of nine-time All-Star Damian Lillard. Before Holiday could suit up for the Trail Blazers, the Celtics traded for him, and immediately benefited.
Holiday bolstered a Boston squad that was already flush with talent. He did so on both sides of the ball, knocking down 3-pointers at a high rate on offense and then stifling opponents with his excellent on-ball defense on the other end of the floor.
Jrue Holiday wasn’t in Boston for long, but I don’t think any Celtics fans will forget this moment from the 2024 title run.
He’s a two-time champ for a reason.
pic.twitter.com/mGzFgFqMlR— Daniel Donabedian (@danield1214) June 24, 2025
The Celtics would've loved to keep Holiday around for longer, exemplified by the inking of a four-year, $135 million extension with the two-time All-Star just ahead of the 2024 playoff run that culminated in banner no. 18. However, that contract was a major reason why they traded him.
Although losing a member of their championship core stings, the Celtics could be better for it in the long run. Here are three reasons why Boston's blockbuster move was a solid to start to its strenuous summer.
Anfernee Simons' contract works for the Celtics
The biggest issue plaguing the Celtics this offseason has nothing to do with X's and O's. It revolves around dollar signs.
Since the Cs are over the second apron, they'll face titanic taxes and further penalties if they're unable to shed some significant salary prior to the end of the 2025-26 league year. Relocating Holiday passes on his hefty contract (in which he's owed over $104 million in the next three years) and inches Boston closer to financial freedom.
Post Holiday trade pic.twitter.com/eftLsP4wAO
— Bobby Marks (@BobbyMarks42) June 24, 2025
While the Celtics still have to lose $18 million to avoid the second apron, the next year of Simons' contract is $7 million cheaper than Holiday's. Better yet, Simons is an unrestricted free agent once the 2026-27 season begins. That means he's on an expiring, “prove-it deal,” giving Boston the chance to either extend him if he excels or let him walk if he disappoints.
With Simons, the Celtics' president of basketball operations, Brad Stevens, can save money and inject some new blood into his team. Of course, his work is far from finished. The Celtics haven't escaped the second apron, and to do so, more trades will be needed.
The Celtics get another scorer in Jayson Tatum's absence
The trajectory of the Celtics' 2025-26 campaign was forever changed once star Jayson Tatum ruptured his right Achilles tendon in the 2025 NBA Playoffs.
The six-time All-Star led the C's in points, rebounds, and assists during the regular season. Replacing his production will be extremely difficult, but Simons helps with that.
He's averaged at least 17 points per game in each of his last four seasons and has never been shy about putting up shots. Behind 2024 NBA Finals MVP Jaylen Brown and Olympic gold medalist Derrick White, Simons can serve as a strong third scoring option while Tatum rehabs for an extended period of time.
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Simons could jump up the depth chart if the Celtics pull off another huge trade in the coming months. But even if he doesn't, his offensive contributions should still exceed what Holiday would've brought to the table. Holiday's average of 11.1 points per outing last season was the lowest of his career since his rookie year, more than a decade ago.
The vet didn't have to be a pure scorer because the Celtics could rely on Tatum and Brown to do most of the heavy lifting. With Tatum out, everything obviously changed, making Simons a logical solution to a potential scoring emergency.
Simons fits Joe Mazzulla's offense
For the last two seasons, the Celtics have led the league in 3-point attempts by a wide margin. And if there's anyone who thrives around the perimeter, its Simons.
OH MY GOODNESS ANFERNEE SIMONS! HE CANNOT MISS RIGHT NOW!
22 PTS ON 6 THREES IN Q3 ON NBA TV. 🔥 pic.twitter.com/5eUss73GUM
— NBA (@NBA) October 25, 2022
The Florida native netted the 17th most 3-pointers of any player during the regular season. He's also averaged more than eight attempts from deep in three straight seasons. Despite his high volume, Simons has shot an impressive 38.1% from 3-point land in his seven years in the league.
Whether he's creating his own shot or opening from beyond the arc, Simons is comfortable shooting triples. That should gel well with Celtics head coach Joe Mazzulla's 3-centric offense, which prioritizes finding good, clean looks at the 3-point line.
The former Blazer is a premier shooter in the NBA, yet he's far from a 3-and-D guy. He's not a great defender, and that's especially apparent when comparing him to the three-time All-Defensive First Teamer he was exchanged for.
However, he's a plus on offense in a time when Boston needs scoring. It also doesn't hurt that he comes with two second-round picks and a cheaper contract.
If money weren't an issue, the Celtics would've continued to roll with Holiday. He was a positive force in Boston's locker room and complemented the talents of Tatum and Brown well, all while serving the community and becoming the NBA's 2024-25 Social Justice Champion.
It's no secret that Simons will have big shoes to fill if Boston doesn't move him again this offseason.
