Three moves Red Sox should make in MLB offseason: Trade notable name, acquire multiple starters

Major League Baseball’s offseason is underway. Trades and free-agent activity are sure to pick up over the coming weeks, before hitting a fever pitch at this year’s edition of the MLB Winter Meetings (scheduled to begin on Sunday, Dec. 3). If there’s one thing the early offseason is good for, it’s halfwits pretending they’re general managers and sketching out elaborate offseason plans. Does that sound enjoyable to you? Then, hey, this is your lucky day. 

Below, CBS Sports has roleplayed as new Red Sox GM Craig Breslow and laid out a few moves we think he should pursue this winter. It should (but won’t) go without saying that this is only for entertainment purposes. MLB executives cannot snap their fingers and make something happen just because they want it to happen. Just suspend your disbelief and enjoy the gasbaggery, please.

Now, with that out of the way, here are three moves we think the Red Sox should make this winter.

1. Find a couple of starters

We’re beginning with an obvious area of need. The Red Sox’s rotation ranked 22nd in the majors in ERA last season. Nine different pitchers received at least five starts, including reliever/opener Brennan Bernardino and free agent James Paxton. Breslow presumably has Chris Sale, Brayan Bello, and Kutter Crawford penciled into his 2024 rotation. That still leaves two spots for acquisitions.

The good news about this free-agent and trade class is that there are a lot of decent starting pitchers available. The bad news is that there are a lot of teams seeking out decent starting pitchers, meaning any additions won’t come cheap or easy. Still, we think the Red Sox should be able to snag a pair of upgrades.

Our guess is that the most realistic approach has Boston signing or trading for one well-above-average starter and then nabbing another who is closer to No. 3 or No. 4 status. We’re supposed to be roleplaying as Breslow here, so we’ll take it a step further and pick two names to satisfy everyone’s lizard brain.

For the top-end starter, we’ll go with newly crowned National League Cy Young Award winner Blake Snell. Some front-office types we talked to are lower on Snell than you might expect based on his command and workload. Still, Snell has demonstrated that he can thrive in the AL East, and it never hurts to add a multiple-time Cy Young Award-winning lefty to a rotation. 

As for the downmarket acquisition, let’s get creative by highlighting a trade target. Athletics right-hander Paul Blackburn is a former All-Star who saw his strikeout rate tick up last season. He doesn’t throw hard and he’ll soon turn 30, but he’s the kind of under-the-radar addition who would make sense.

If Breslow really wants to get funky, he could bring in Tyler Mahle on a one- or two-year deal. Mahle underwent Tommy John surgery in May, suggesting he won’t be up for a return to the mound until around the All-Star Game. Even so, he has a track record of being an above-average starter and he could serve as a nice midseason boost. Besides, teams always need more than five starters on account of injuries and underperformance. 

2. Trade Verdugo for infield help

Again, not a novel suggestion. 

The Red Sox have reportedly discussed Alex Verdugo in past trade talks. Why wouldn’t they continue to do so this winter? He’s entering his walk season, and he’s established himself as a league-average player who has the tendency to annoy his manager. Our hunch is that his trade value isn’t super high.

Nevertheless, moving Verdugo could remove one headache for Alex Cora while potentially helping the Red Sox shore up another part of their roster. Specifically, we would try to trade Verdugo for some infield help. The Red Sox have Trevor Story, Rafael Devers, and Triston Casas in place. That leaves an opening at either second base or shortstop, depending on where Story plays.

The free-agent market is dreadful for middle infielders, making the trade market more welcoming for addressing this opening. There are a few teams who have clear infield surpluses: the Orioles, Guardians, Rangers, Yankees, and Padres among them. We don’t think all of those teams would have interest in Verdugo, and, again, we’re not convinced they’d move their most attractive infielders for him even if they did (otherwise we suspect Gleyber Torres would already have changed teams).

Perhaps we could get lucky, though, and ship Verdugo and a lesser prospect to the Guardians for Tyler Freeman, a pure contact hitter who could slot in at second base. It’s not the world’s most attention-grabbing move, but it could pay off if Freeman could mimic early-career David Fletcher for a few seasons.

3. Add a true center fielder

Speaking of necessary, if boring maneuvers. 

With Verdugo out of the way, we would slide Jarren Duran to a corner and bring in a quote-unquote real center fielder. (Duran, despite his great speed, has graded as a below-average glove there throughout his big-league tenure.)

The free-agent market is rich in this respect. Kevin Kiermaier is the biggest name, but South Korean transfer candidate Jung Hoo Lee might offer the most upside. There’s also Michael A. Taylor, coming off a better two-year run at the plate than his reputation suggests, as well as Harrison Bader, an ideal candidate for a one-year pillow contract. 

Adding any one of those would bolster the Red Sox’s defense up the middle.