2. Sign an Ace
MLB free agency doesn't begin until after the World Series, so Breslow will have to wait a little bit for this one. But if there's one thing Boston needs this winter, it's a top-end starting pitcher.
The Red Sox didn't have one last season, and it showed. Corey Kluber was the Opening Day starter and ended up being one of the worst pitchers in baseball, going 3-6 with a 7.04 ERA. Chris Sale used to be an ace but is perpetually hurt, and Brayan Bello isn't quite there yet.
Fortunately, there's going to be plenty of big-name pitchers on the free agent market this offseason. Clayton Kershaw, Blake Snell, Aaron Nola, Sonny Gray, Jordan Montgomery and Eduardo Rodriguez are just some of the high-profile arms that will be available.
Breslow's No. 1 goal should be getting at least one of them. Nola would be ideal given his durability, postseason success and proven track record in a tough market, but honestly any of them will do. They just need to sign someone to bolster their rotation, because they can't afford to run it back with the same group next year.
Boston ranked 27th in innings and 22nd in ERA from its starting pitchers last year, so the rotation is a major problem that needs to be addressed. As a former pitcher himself, Breslow should be the right man for the job.