What Red Sox's Perfect Roster Looks Like After Sept. 1

There's one veteran we don't think would be on it

Red Sox outfielder Roman Anthony makes he way through the home tunnel at Polar Park on Aug. 25, 2026. Anthony is currently on a rehab assignment with the WooSox. | USA TODAY Network via Reuters Connect

Roster crunch time has nearly arrived for the Boston Red Sox.

On Thursday, it seemed more certain than ever that by the start of the team's series with the New York Yankees on Friday, changes would happen. The only question was how many rehabbing major leaguers would rejoin the squad — one or two.

Roman Anthony and Trevor Story are angling to return quickly, while Isiah Kiner-Falefa has said publicly he's okay with waiting until the Sept. 1 roster expansion to come back. So to be productive, let's draw up a dream version of the 28-man roster for the last month of the season — and go over whether all three of those guys should be on it.

Position Players

Aug 17, 2026; Boston, Massachusetts, USA; Boston Red Sox shortstop Mickey Gasper (30) hits a home run against the Arizona Diamondbacks in the seventh inning at Fenway Park. Mandatory Credit: David Butler II-Imagn Images | IMAGN IMAGES via Reuters Connect

Let's rip the band-aid off. The reason we're covering this topic is that unless someone gets injured or falls into a serious slump, the best version of this Red Sox roster doesn't have Story on it.

Not only was he one of the worst hitters in baseball early in the year before his injury, but he's been abysmal in Triple-A on his rehab stint, as if to confirm that he can't be trusted to contribute offensively. If only one infielder can come back, it should be Kiner-Falefa. Even if we don't trust it will play out that way, that's what we think the perfect roster looks like.

Nick Sogard and Andruw Monasterio have earned the right to stay. Mickey Gasper is hitting out of his mind. Kiner-Falefa replaces Anthony Seigler, and that's about it.

Will Story come back? Almost definitely. Should the Red Sox mess up the chemistry they currently have by re-inserting a struggling veteran? It's hard to imagine it will help.

Pitchers

Aug 17, 2026; Boston, Massachusetts, USA; Boston Red Sox pitcher Alec Gamboa (68) throws a pitch against the Arizona Diamondbacks in the first inning at Fenway Park. Mandatory Credit: David Butler II-Imagn Images | IMAGN IMAGES via Reuters Connect

Now it gets a lot easier. The main question to consider is health. If the bullpen gets healthy, the Red Sox could be cooking with gas.

Garrett Whitlock should be back within a week, while Justin Slaten isn't far behind. Two arms in means only one has to go out, assuming there are no other injuries in the meantime.

The choices to be sent down to Triple-A come down to Alec Gamboa, Wyatt Olds, and Greg Weissert. And while Olds is the least experienced (and therefore proven), Weissert has blown up in enough situations this year to at least strongly consider making him the odd man out.