2. Chris Sale
A wise man once said: "the best ability is availability." In the case of Chris Sale, he really lacks ability then.
Since the end of the 2019 season, Chris Sale has thrown 146 innings. For comparison, Gerrit Cole of the Yankees has thrown 664 innings in that span. Oh, and Sale's collected $117.5 million worth of paychecks during that stretch.
Sale isn't solely responsible for his litany of injuries, but he is due $27.5 million this year, and for a team that has dropped salaries like a bad habit, it's surprising that he is still on the roster and cashing checks. Breslow's predecessor Bloom reportedly had an opportunity to trade Sale in 2022, even after the southpaw had broken his finger, with the "mystery team" offering to take on all of Sale's remaining salary.
At the Winter Meetings, Breslow gave Sale an unequivocal vote of confidence when asked if he should be expected to make 25 starts in 2024 (something Sale hasn't done since 2019).
"I don’t know why we would say he shouldn’t, right? He’s as healthy as he’s been (in a while) at this point. I think he has the benefits of a normal ramp-up and a normal offseason. I think he’s probably understanding and we’re understanding how to help him recover and take care of himself...I don’t know why I wouldn’t sit here and say we expect a full healthy season."- Craig Breslow, Per Sean McAdam
If Breslow does hold onto Sale, it will be because there is little interest for him on the trade market and the club is holding onto a Hail Mary attempt that Sale can somehow return to his Cy Young-caliber form.
It's long overdue for Boston to finally sever ties with Sale. Shedding his contract would allow the team more flexibility during this pivotal free agency, where the Red Sox appear to be predominantly focused on finding pitching. The biggest challenge will be finding a willing trade partner. Maybe Chaim Bloom can introduce Breslow to the mystery team.