The Red Sox have been here before, and that’s what makes this week in Las Vegas so interesting.
The GM meetings are always a place where baseball’s power brokers start laying winter track, but this year carries a little extra urgency. With the Winter Meetings likely to be canceled if there isn’t a new CBA by Dec. 1, the window for bold action could be narrower than usual. That puts Craig Breslow in the spotlight, with one obvious question hanging over him: can he make a move with the kind of impact Boston once pulled off at this same event?
The answer to that question takes you back to November 2015, when the Padres first brought Craig Kimbrel into the conversation at the GM meetings and Dave Dombrowski finished the deal by Nov. 13.
Boston paid a heavy price at the time, sending Manuel Margot, Javier Guerra, Carlos Asuaje and Logan Allen to San Diego. In return, the Red Sox got a 27-year-old, four-time All-Star who had just finished his fifth straight season with at least 39 saves.
Kimbrel already had 225 career saves and a 1.63 ERA that stood as the lowest ever through an age-27 season.
That trade ended up mattering a whole lot more than it looked on paper in the moment. Kimbrel made the All-Star team in each of his three seasons with Boston, racking up 108 saves and 305 strikeouts in 184 1/3 innings across 187 relief appearances.
His 2017 season was especially electric: 35 saves, a 1.43 ERA and 126 strikeouts in 69 innings. Then came 2018, when he saved 42 games for a 108-win club and, despite a rough October that included a 5.91 ERA over 10 2/3 innings, still picked up six postseason saves on the way to a title.
Boston eventually let him go. Kimbrel turned down the qualifying offer, didn’t sign until June 2019 with the Cubs, and has since bounced around 10 major league clubs, most recently signing with the Royals in August. For the Red Sox, it was a case of getting exactly what they wanted and moving on at the right time.
Now Breslow faces a different kind of pressure, but the need is easy to see. Boston finished 26th in home runs and managed only two runs in its Wild Card sweep against the Yankees.
Elly De La Cruz is still the dream target, and the Reds already rejected a prospect-heavy deadline offer because they wanted young major leaguers instead. Jim Bowden expects Boston to keep checking in on De La Cruz and Nationals shortstop CJ Abrams, while MassLive’s Sean McAdam wouldn’t be surprised if Jarren Duran and Masataka Yoshida are moved to make it happen.
The front office has already shown how aggressive it can be, and there are deals Breslow could potentially get done quickly this week. He has also said that anyone claiming to know where the labor talks will end up is probably wrong, which is part of why there’s a case for acting now under the current rules.
Boston has done this before. If Breslow can pull off something similar in Las Vegas, the Red Sox could give their fans a real lift heading into a long lockout winter and a reason to feel better about 2027.
In Other News...
Red Sox Roster Squeeze Could Force Breslow To Move Key Pieces
The Red Sox have already started trimming the edges of their roster, and the next wave of moves could be more meaningful than simple housekeeping. With the 40-man picture still crowded and payroll decisions looming, chief baseball officer Craig Breslow may have to keep working the phones to create room, especially if Boston wants to keep its outfield situation from turning into a logjam.
One avenue being floated is a deal with the Mariners for a controllable starting pitcher, a move that would fit both the present and the longer view. Another possibility is moving utility man Romy Gonzalez, part of a broader effort to clear space and shape the roster with an eye on 2027, even if the exact sequence of trades is still very much in the recommendation stage rather than a finished plan. [Read more 🡒]
Former Red Sox Reliever Zack Kelly Opens Up After Boston Move
Zack Kellys run with Boston ended the way so many bullpen stories do, with a roster squeeze and a fresh start somewhere else. The right-hander was designated for assignment and then released by the Red Sox, putting him on the open market after a stretch that included 115 major league appearances and a 4.04 ERA in a Boston uniform.
Kellys 2026 season was interrupted by right elbow inflammation, which cut short what had been another chance to carve out a steady role. Now he is expected to look for his next opportunity with another club, most likely on a minor league deal that comes with a Spring Training invitation, and the next step will be finding a team willing to bet on his arm and his experience. [Read more 🡒]
Red Sox Face A Serious New Threat In Key Rotation Chase
The market for starting pitching is already taking shape, and it could have real ripple effects for the Red Sox as they look to shore up their rotation this winter. Reports say the Cubs are expected to be aggressive in the hunt for arms, with Sonny Gray emerging as one of the names to watch, which only adds another big-market club to a pursuit that figures to be crowded from the start.
Chicago has reportedly taken Tarik Skubal off its board, but Gray remains in play as the offseason rumor mill keeps turning. The Braves are among the other teams said to be involved, and with no deal close and no clear resolution yet, Boston is left watching a market that may get more expensive and more competitive by the day. [Read more 🡒]