Fantasy Sports

Boston Celtics Fleece Portland Trail Blazers—Fantasy Basketball Fallout

Alan Goldsher|
Jrue Holiday
Jrue Holiday | Bob DeChiara-Imagn Images

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Boston CelticsPortland Trail Blazers

It’s always fun to wake up to a ShamsBomb:

First off, let’s get the obvious out of the way: Boston Celtics general manager Brad Stevens just took Portland Trail Blazers GM Joe Cronin out to the back playlot and stole his milk money.

You see, Jrue Holiday is an elite guard, a two-time All-Star, and, by all accounts, one of the best locker room guys in the Association. But he’s entering his age-35 campaign—his 17th in the league—and in both of his seasons with the Celtics, he averaged the fewest points since his rookie year. And in 2024-25, he compiled 3.9 nightly assists, again the least since he was a freshman.

Yes, some of that can be explained away by the fact that Holiday spent most of his time on the floor with ball-dominant wings Jayson Tatum and Jaylen Brown, but he still played 31 minutes a night, just one-plus minutes lower than his career average. That’s a ton of statistical regression for sixty-ish fewer seconds a contest

Even more problematically for Portland, Holiday is on the books through the 2027-28 season, and his contract will be hard to move, as over the next three seasons, it climbs from $32 million, to $34 million, to $37 million. Yikes.

It could be argued that Portland needs some veteran blood, but giving up an electric 26-year-old to do so—especially one who’s averaged 21.0 points and 4.8 assists over the last three seasons—is a baffling call. The fact they also sent over some draft capital makes the whole thing even weirder.

For Boston, it opens up the doors for more possible moves. Is Jaylen Brown next? Is Derrick White expendable? Is anyone safe at all?

If Brad Stevens can find more suckers like Joe Cronin, anything’s possible.

Meanwhile In Fanatsyland..

It’ll be hard to make any concrete fantasy prognostications until the dust settles in Boston—you know Stevens isn’t done yet—but as of right now, it looks like Simons’ value will take a hit, as he’ll be playing second fiddle to Brown…or maybe even second-and-a-half fiddle to Kristaps Porzingis.

Brown’s fantasy value—which kinda skyrocketed after Tatum went down—could fall back to Earth, because Simons will have to get some notable burn and usage, if only to justify the trade. White will also get dinged, as Simons’ presence could return him to his sixth-man role.

Up in Rip City, Shaedon Sharpe might be quietly celebrating, as Holiday is a more willing ball-sharer than Simons, thus opening up plenty of shots for the 22-year-old Kentucky product, potentially making him worthy of third-round consideration.

Maybe even late second.

Additionally, Holiday has elite floor vision, so Blazers’ wings Deni Avdija and Toumani Camara could also see three or four more attempts a night.

And the Winner Is…

Simply put, Boston crushed the reality show—Simons nicely sets the table for the Jayson Tatum 2.0 era—while Portland, at least here in 2025, is now a team filled with slick on-the-D.L. fantasy chips.

Which is great for fantasy nerds like you and me, but it ultimately won’t save Joe Cronin his job.

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Alan Goldsher
ALAN GOLDSHER

Alan Goldsher has written about sports for Sports Illustrated, ESPN, Apple, Playboy, NFL.com, and NBA.com, and he’s the creator of the Chicago Sports Stuff Substack. He’s the bestselling author of 15 books, and the founder/CEO of Gold Note Records. Alan lives in Chicago, where he writes, makes music, and consumes and creates way too much Bears content. You can visit him at http://www.AlanGoldsher.com and http://x.com/AlanGoldsher.

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