In his brief Celtics tenure, Jrue Holiday has been everything Boston hoped he’d be and more.
An All-Defensive caliber force, timely scorer, versatile playoff performer and ultimate locker room guy. He’s a consummate professional, and he’ll go down in Celtics’ lore as a key piece in helping the franchise garner its ever-elusive 18th championship banner last June.
But the NBA is a business, and Celtics’ president Brad Stevens made yet another intelligent business decision on Monday night by dealing the 35-year-old guard to Portland in exchange for an impressive haul.
Holiday — who has a player option in 2027-28 and was due to make $32.4 million this year and $34.8 million next year— was somehow enough to land sharpshooting guard Anfernee Simons and two second-round picks.
It was a homerun move, especially when considering the fact that C’s superstar Jayson Tatum will be on the shelf for most, if not all, of the upcoming season as he rehabs from Achilles’ surgery. Boston needed to fill at least some of Tatum’s offensive void, and adding Simons is a great start.
For all intents and purposes, there really aren’t any negatives to the pre-draft swap.
First and foremost, Boston sheds a massive contract for an aging player who while still productive, unquestionably digressed this past season. The Celtics’ projected tax savings for the upcoming campaign are now estimated at $40 million, putting them around $18 million below the second apron and allowing more flexibility to further fill out the roster.
Simons, meanwhile, is on an expiring contract, due to make $27.6 million this year before becoming an unrestricted free agent. If he sticks around — who knows what Stevens’ end game is with him — and plays well, maybe he’s a guy you sign to a long term deal. If he proves to be a poor fit, there’s no harm in either trading him midseason or letting him walk next summer without owing him a dime more.
My guess is Simons will be a perfect fit for the looming “bridge” year in Boston, especially in coach Joe Mazzulla’s 3-point happy offense. The C’s are unlikely to contend for a title without Tatum but are still very much in the mix for a top four playoff seed in an overall weak Eastern Conference.
At 26, Simons will be entering his eighth year in the league and has averaged 21 points and 4.8 assists per game over his last three seasons with the Blazers. He’s a volume scorer out of the backcourt, launching around 17 shot attempts per game while knocking down 38 percent of his threes for his career.
While nowhere near the defender Holiday is, the 6-foot-3 Simons makes up for it with crafty ball handling skills, premier outside shooting and the ability to finish athletically around the rim. His offensive bag is deep, and he boasts the potential to explode on any given night.
No, Portland hasn’t qualified for the postseason since 2020-21, so Simons’ stats may be a bit inflated having run the show for a middling squad since franchise cornerstone Damian Lillard was traded to Milwaukee back in 2023. But 20 points per game is 20 points per game, and there’s no reason to believe he can’t put up similar numbers alongside Jaylen Brown and Derrick White this coming year.
It’s simply a low risk, high reward type move, and all signs point to it being the first of perhaps many similar deals for Stevens and Co. this offseason.
Making a seismic splash by trading someone like Jaylen Brown still appears far fetched, but with Stevens running the show, it’d be wise not to rule anything out.
Nick Giannino covers the Boston Celtics for CNHI Sports Boston. Contact him at NGiannino@nobmg.com and follow him on Twitter/X @NickGiannino_GT.