Celtics
Simons’ 3-point shooting could make him a key scorer in Joe Mazzulla’s system.
A busy offseason for the Celtics finally commenced on Monday night, with Boston reportedly trading Jrue Holiday to Portland Trail Blazers.
While shedding the remainder of Holiday’s contract (three years, over $100 million) might have stood as Boston’s top priority in this deal, the Celtics did more than just lessen some of what was shaping up to be an historic luxury-tax bill next season.
The Celtics also landed guard Anfernee Simons and two second-round picks in return for Holiday — with the 26-year-old Simons offering plenty of appeal as either a potent scorer in 2025-26 or even a trade chip moving forward.
Here are five things to know about Boston’s new guard:
Simons has been an effective scorer for Portland.
With Jayson Tatum potentially sidelined for most (if not all) of the 2025-26 season after rupturing his Achilles tendon during the 2025 playoffs, the Celtics could use some additional scoring punch in 2025-26 beyond Jaylen Brown and Derrick White.
Simons could fit the bill, given his track record with the Trail Blazers.
While he was originally drafted by Portland in 2018, Simons established himself as a regular starter during the 2022-23 season. Over these last three seasons, the 6-foot-3 guard has averaged 20.7 points and 4.7 assists per contest while shooting 37.4 percent from 3-point range.
His best season with Portland came in 2023-24, when he scored a career-best 22.6 points per game while sinking 38.5 percent of his 3-point shots.
Even though Simons is not nearly the same defender as Holiday, his arrival at least gives Boston another dependable scoring option entering a season where the Celtics might be hard-pressed to generate offense with Tatum on the mend.
He should fit in well in Joe Mazzulla’s system.
When it comes to finding potential fits for Joe Mazzulla’s 3-point-heavy approach on offense, Simons checks off plenty of boxes.
Sinking shots from 3-point range has served as one of Simons’ go-to avenues toward racking up points, with the Florida native boasting a career 38.1 shooting percentage from beyond the arc.
This past year, Simons converted on 36.3 percent of his 3-pointers while attempting 8.5 treys per contest — which would have ranked third on the 2024-25 Celtics behind Tatum and Derrick White.
Simons converted on 215 3-pointers in 2024-25 — which ranked 17th in the league, albeit fourth overall on a Celtics team committed to 3-point shooting under Mazzulla’s tutelage.
As noted by WEEI’s Justin Turpin, Simons ended this last season on a high note. From the start of the new year through the end of the regular season, Simons averaged 3.4 made 3-pointers per game — which ranks as the fifth most in the league during that span (minimum 30 games played) behind only Steph Curry, Anthony Edwards, Malik Beasley, and Derrick White.
Simons does give Boston options with his contract.
Even though Simons’ arrival does give Boston another 3-point threat and regular scorer in Tatum’s absence, his expiring contract also gives the Celtics some flexibility.
Simons’s contract will cost the Celtics $27.2 million in 2025-26 before the guard has the option to test free agency.
Even though Simons is extension-eligible with the Celtics, Boston could also let things play out this season and see whether or not he’s a long-term fit with the roster before committing to him on a Tatum-led team in 2026-27 and beyond.
If the Celtics opt to let Simons walk next season, getting that $27.2 million off the books would further help Boston sneak below the luxury tax and other restrictive aprons. Granted, it also remains to be seen what else Brad Stevens has planned in the coming days as far as augmenting this roster.
Simons’ expiring contract could also make him a potential trade chip for Boston this year, especially if Boston is heading toward a bridge year with Tatum on the sidelines.
He went straight from prep hoops to the NBA.
Simons was one of the few NBA players who managed to skip playing college basketball or international competition before arriving to the pros.
Since 2006, drafting high school players has been prohibited by the NBA collective bargaining agreement, which stipulates that players who enter the draft be 19 years of age or older and at least one year removed from high school.
But Simons took advantage of a loophole that allowed him to avoid a season playing college basketball — as he played for IMG Academy as a fifth-year prep in 2017-18 despite technically graduating high school the year before.
While other NBA players like Scoot Henderson used the G League as an avenue to play in their bridge year before the NBA Draft, Simons was one of the first to take advantage of prep basketball in order to comply with the league’s “one-and-done” ruling before the draft.
After his tenure at IMG, Simons was drafted by Portland with the 24th pick in the 2018 NBA Draft.
He was named after an NBA star.
Simons was linked to the NBA before he ever stepped foot on the court with the Trail Blazers. Simons’ parents — who were fans of the Orlando Magic — opted to name him after Orlando star guard Anfernee “Penny” Hardaway.
“I liked the uniqueness of the name—and, of course, I liked Penny,” Simons’ father, Charles, told Bleacher Report’s Jason King in 2018. “He was from Memphis and I grew up in Nashville.”
Both Simons and Hardaway ended up getting to know each other over the years, as Penny’s son, Jayden, also attended IMG Academy with Simons.
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