Monday night marked the official start of the Celtics’ hectic offseason, as Boston allegedly traded Jrue Holiday to the Portland Trail Blazers.
The Celtics did more than merely reduce a portion of what was expected to be a historic luxury-tax burden for the upcoming season, even though cutting the remaining three years and more than $100 million of Holiday’s contract might have been Boston’s prime aim in this agreement.
In exchange for Holiday, the Celtics also acquired guard Anfernee Simons and two second-round picks. The 26-year-old Simons has a lot of potential as a trade chip in the future or as a strong scorer in 2025–2026.
Five facts regarding Boston’s new guard are as follows:
Simons has been an effective scorer for Portland.
The Celtics could use some extra scoring punch in 2025–26 in addition to Jaylen Brown and Derrick White, as Jayson Tatum may miss the most of the 2025–26 season due to an Achilles tendon rupture during the 2025 playoffs.
Given his history with the Trail Blazers, Simons would be a good fit.
Despite being selected by Portland in the 2018 NBA Draft, Simons became a consistent starter in 2022–2023. The 6-foot-3 guard has shot 37.4 percent from 3-point range and averaged 20.7 points and 4.7 assists per game over the past three seasons.
In 2023–24, he had his best season with Portland, scoring a career-high 22.6 points per game and making 38.5 percent of his 3-point attempts.
Simons is not nearly as good of a defender as Holiday, but at least he gives Boston another reliable scoring option going into a season in which the Celtics may struggle to score with Tatum recovering.
THE BUZZERBLAZERS’ ANFERNEE SIMONS WIN.pic.twitter.com/Mse5aiK3Br
He should fit in well in Joe Mazzulla s system.
Simons is an excellent fit for Joe Mazzulla’s offensive strategy, which relies heavily on 3-point shooting.
The Florida native’s go-to method for scoring points has been making 3-pointers, as seen by his career 38.1 shooting percentage from outside the arc.
Simons attempted 8.5 3-pointers per game and made 36.3 percent of his 3-point attempts last season, which would have placed him third on the 2024–25 Celtics behind Derrick White and Tatum.
In 2024–25, Simons made 215 3-pointers, good for fourth overall but 17th in the league, on a Celtics squad that was dedicated to 3-point shooting under Mazzulla’s guidance.
According to Justin Turpin of WEEI, Simons concluded the previous season with a bang. Simons averaged 3.4 3-pointers per game from the beginning of the season until the end of the regular season, which is the fifth-highest in the league during that time (at least 30 games played), behind Derrick White, Steph Curry, Anthony Edwards, and Malik Beasley.
Welcome to Mazzulla Ballpic, Anfernee Simons.Twitter: https://F3TXzgjrqr…
Simons does give Boston options
with his contract.
In Tatum’s absence, Simons’ presence does provide Boston with a regular scorer and another 3-point threat, but the Celtics also have some leeway because of his contract expiration.
The Celtics will pay $27.2 million for Simons’ deal in 2025–2026 before the guard may choose to test free agency.
Boston might wait until the end of this season to determine if Simons is a long-term fit with the team before committing to him on a Tatum-led squad in 2026–2027 and beyond, even though he is eligible for an extension with the Celtics.
Getting that $27.2 million off the books would help Boston evade the luxury tax and other limiting measures if the Celtics decide to let Simons depart next season. Granted, it’s also unclear what more roster additions Brad Stevens has in store for the days ahead.
If Boston is going to have a bridge year with Tatum out, Simons’ contract expiration might potentially make him a possible trade piece this season.
He went straight from prep hoops to the NBA.
One of the rare NBA players to make it to the professional ranks without participating in international competition or collegiate basketball was Simons.
According to the NBA collective bargaining agreement, which has been in effect since 2006, players who enter the draft must be at least one year out of high school and be at least 19 years old.
Although Simons officially graduated from high school the previous year, he played for IMG Academy as a fifth-year prep in 2017–18, taking advantage of a loophole that prevented him from playing a season of college basketball.
Simons was among the first to use prep basketball to get around the league’s one-and-done rule before to the draft, while other NBA players, such as Scoot Henderson, used the G League as a way to play in their bridging year before the NBA Draft.
Simons was selected by Portland with the 24th pick in the 2018 NBA Draft following his time at IMG.
He was named after an NBA star
.
Before Simons even set foot on the court with the Trail Blazers, he was connected to the NBA. Simon was named after Orlando great guard Anfernee Penny Hardaway by his Orlando Magic-supporting parents.
As Simon’s father, Charles, told Bleacher Report’s Jason King in 2018, “I liked the uniqueness of the name and, of course, I liked Penny.” I was raised in Nashville, and he was from Memphis.
Since Penny’s son, Jayden, also attended IMG Academy with Simons, Hardaway and Simons eventually became acquainted.
Since 2023, Conor Ryan has worked as a staff writer for Boston.com, covering the Boston Bruins, Celtics, Patriots, and Red Sox.
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