The Boston Celtics are navigating an offseason full of questions and strategic pivots — and the front office still isn’t done tinkering. After reports indicated the Celtics and Memphis Grizzlies were exploring trade opportunities, the trade machines have been fired up.
One idea — floated by Jake Issenberg on First to the Floor: A Boston Celtics Podcast — would send Kentavious Caldwell-Pope to Boston in exchange for Anfernee Simons, a straight-up deal that could quietly benefit both sides in what’s already been a transformative summer.
KCP Saves Celtics $6 Million
Boston’s motivation is twofold: create financial flexibility and add veteran leadership. Simons is a gifted scorer, but his defensive issues are hard to ignore. Caldwell-Pope, meanwhile, brings perimeter defense, three-point shooting, and championship poise — even if his production dipped last season.
The proposed deal would save the Celtics around $6 million, taking them further below the second apron after waiving JD Davison. Every dollar matters right now, especially with the Celtics already locked into massive extensions for Jayson Tatum and Jaylen Brown.
From Memphis’s side, Simons offers something they badly need: scoring. With Desmond Bane now in Orlando and Ja Morant likely forced to carry the offense more than he ever has before, Simons could provide an instant offensive spark and help lighten the backcourt load as the Grizzlies reset their core.
— 20.6 PPG — 5.1 APG — 3.2 3PM
The newest Boston Celtic.
Perfect Fit for Mazzulla’s Celtics?
Caldwell-Pope isn’t the same player he was during the Lakers’ 2020 title run or even the Nuggets’ 2023 championship season, but he still profiles as an ideal fit for Joe Mazzulla‘s system.
In his most recent championship year, KCP averaged 10.8 points, 2.7 rebounds, and 2.4 assists, while shooting 42.3% from deep — an elite mark for a 3-and-D wing.
His contract — two years, $43 million — is still reasonable for a rotation-caliber veteran. And compared to Simons’ expiring deal, it gives Boston less short-term flexibility, but more consistency in the locker room.
Jrue Holiday Kentavious Caldwell-Pope Alex Caruso
Risky Business
The risk for Boston comes in the form of timing. Simons is on an expiring contract. If he walks next summer, they gain flexibility. But Caldwell-Pope’s deal runs through 2027, and if his value continues to drop, the Celtics could be stuck paying for past rings instead of current production.
There’s also no guarantee that KCP rediscovers his peak form. His scoring and usage dropped in Orlando last season, and he looked more like a depth piece than a difference-maker.
Still, Boston isn’t looking for a star. They’re looking for glue guys who can shoot, defend, and show up in May. Caldwell-Pope still checks those boxes — even if only in pencil, not pen.
What Comes Next?
This isn’t the flashiest move, but there’s logic here. Boston gets under the second apron and adds a two-time champion. Memphis gets a young scoring guard who could thrive alongside Morant.
If nothing else, this pitch shows the kind of calculated swings the Celtics might need to keep contending. And in an offseason full of questions, adding a player who’s already been there — twice — might be one of the safer answers.
Celtics Trade Pitch Lands Them 2x NBA Champion