Four Questions Red Sox Face Before Craig Breslow’s First GM Meetings

It won’t take very long for the Boston Red Sox to see what Craig Breslow’s capable of, as his first big test is right around the corner.

In fact, it’ll come less than one week into the job.

The 2023 Major League Baseball general managers meetings begin Tuesday in Scottsdale, Ariz. The event will be Breslow’s first league-wide gathering since being named Red Sox chief baseball officer this past Thursday at Fenway Park, giving him an opportunity to shake and move for the first time.

There’s no guarantee anything big will happen, but Breslow and the Red Sox have plenty of questions to answer over the next few weeks. We think these are the most notable.

How far will Craig Breslow branch out of his comfort zone?
There’s no team in baseball that Breslow has more familiarity with, including the Red Sox, than the Chicago Cubs. That’s why it would be understandable for the 43-year-old to immediately want to make a move with his former team, whether it be a prospect he had a hand in obtaining or one he values more than Chicago’s current brain trust. We’ve seen similar strategies in the NFL, but it wouldn’t exactly be the best look.

Breslow’s best bet is probably to attack other markets early on. We’re sure he probably had an idea that he wasn’t able to execute in Chicago, and this week is the perfect time to get the ball rolling on that.

Do the Red Sox have extensions in mind?
These meetings aren’t only for general managers. There are plenty of agents that will be in attendance, including the representatives of Brayan Bello and Triston Casas. Breslow has stated he wants to keep young, productive players in Boston, so why wait?

What are the plans for the starting rotation?
There’s one positive to the fact that Boston has had such poor production out of starting pitchers in recent seasons. They can do almost anything this offseason.

The possibilities are endless, which makes it hard to forecast what the Red Sox have in mind. We’ll get out first glimpse this week, though, which sure is exciting.

Will Boston try to get a head start?
We’ve seen teams already make moves this offseason, and more will come at the meetings, with the Red Sox looking like a prime candidate to strike.

Chaim Bloom made a few moves early in the offseason during his tenure, including the infamous Hunter Renfroe-Jackie Bradley Jr. trade in 2021. Boston is back in a spot where upgrade will need to be made, so perhaps they take a similar strategy under new management into the winter.