Breslow can make his mark at Winter Meetings

November 30th, 2023

This story was excerpted from Ian Browne's Red Sox Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.

The attempted reshaping of the Red Sox from last-place finishers the last two years to legitimate postseason contenders in 2024 and beyond will be in full force in the suites and coffee shops and other parts of the massive Gaylord Opryland Resort and Convention Center in Nashville, Tenn., next week.

Executives and agents throughout the sport will arrive on Sunday and leave on Wednesday or Thursday.

This will be new Red Sox chief baseball officer Craig Breslow’s first chance to truly make his mark as a lead executive.

The Red Sox are expected to be more aggressive spenders in free agency than in recent years, but they will also search for value in the trade market. Upgrading the starting pitching will be Breslow’s top mission in Nashville.

Here is a primer for the Meetings.

Key events

  • Sunday, Dec. 3: HOF Contemporary Era ballot results released (Cito Gaston, Davey Johnson, Jim Leyland, Ed Montague, Hank Peters, Lou Piniella, Joe West and Bill White)
  • Tuesday, Dec. 5: Draft Lottery; manager Alex Cora speaks to the media
  • Wednesday, Dec. 6: Rule 5 Draft

Club needs

The Red Sox need starting pitching and everyone knows it. The same could be said last winter, but the club fell short in making the necessary upgrades. Breslow will try to make up for that and it’s safe to assume he will be all in on Nippon Professional Baseball stud righty Yoshinobu Yamamoto, who was recently posted as a free agent by the Orix Buffaloes. Second base is another obvious need for Breslow and Co.

Potential trade candidates

Right fielder Alex Verdugo, the key return piece when the Red Sox traded Mookie Betts to the Dodgers, could be on the move this winter. The left-handed hitter, who was a Gold Glove finalist in right field in 2023, is entering his final arbitration-eligible season. The Red Sox are deep in left-handed-hitting outfielders and Verdugo could be used as a chip to help Breslow acquire pitching and/or a second baseman. Bobby Dalbec, who had a monster 2023 at Triple-A but has fallen out of favor with the big league staff, could also be dealt.

Prospects to know

Ceddanne Rafaela, the club’s No. 3 prospect, is a stud in center field and an above-average defender at short. The question is if he can improve his plate discipline enough to be an everyday player in MLB. No. 4 prospect Kyle Teel, the team’s top pick in the 2023 Draft, is rising fast and could earn a promotion to the Sox as early as '24. Catchers who can hit are hard to find, and that’s why there is an air of anticipation about Teel. No. 17 prospect Wilyer Abreu looked like a polished hitter after his call-up, and he is the outfielder who could make Verdugo expendable.

Rule 5 Draft

It was somewhat surprising that lefty Shane Drohan, who was dominant in his first six starts at Double-A before struggling at Triple-A, wasn’t protected. Given Breslow’s constant deep dive on pitchers and what makes them tick, it wouldn’t be stunning if he grabs an arm in the Rule 5 Draft.

Burning question

Will the Red Sox get the impact pitcher such as Yamamoto, Jordan Montgomery or Blake Snell that they need to get back into the mix in the loaded American League East? If not, a lot will hinge on the continued development of Brayan Bello, Garrett Whitlock, Tanner Houck and Kutter Crawford. Sure, the Sox would also love to keep Chris Sale healthy. But they can’t count on that. All eyes will be on Breslow’s ability to land a No. 1 starter. It will be somewhat stunning if they don’t acquire at least one key starter this winter.