Red Sox winter to-do list: All the tough decisions Craig Breslow faces and more

Entering the regular season, there were whispers that Alex Cora was likely entering his final season with the Boston Red Sox.

But then the Red Sox exceeded expectations and it became increasingly clear just how important that Cora was to the team’s success. So the Red Sox signed Cora to a multi-year extension to keep the veteran manager in Boston, taking arguably the best manager off the market where other teams would surely pounce at the opportunity to snag him.

The Red Sox, however, have since been eliminated from postseason contention. At 80-79, they are in third place in the American League East and face an offseason with uncertainty and external pressure to significantly address the roster.

Red Sox free agent targets

The Red Sox, at least recently, have been one of baseball’s least aggressive teams in the offseason. No, that is not on former executive Chaim Bloom. That is not on Craig Breslow, who replaced Bloom atop the front office. That falls squarely on ownership in Boston.

This offseason needs to be different. The Red Sox have a young core headlined by Rafael Devers that has positioned them to be a contender in 2025 and beyond. They are close. And they are a starting pitcher or two away. 

Among the targets on the Red Sox’s wish list should be Corbin Burnes and Max Fried, both who will command large nine-figure commitments. The good news for the Red Sox, however, is that right-hander Lucas Giolito should be back in 2025 (he was out for the season after undergoing Tommy John surgery) and would appear highly likely to exercise his $19 million player option.

One thing to note: Giolito is represented by the same agency (CAA) as Fried. Perhaps that means nothing, but it’s at least worth mentioning that the two sides have done business together recently.

Will the Red Sox be active in the trade market?

Yes. Upgrading the pitching staff seems like a potential avenue that the Red Sox could explore over trade, and parting from a deep group of young, talented position players across the organization to do so is a legitimate thought.

It’s something to watch over the offseason. I would not rule out a trade of this kind at all for Breslow and the Red Sox.

What free agents should the Red Sox keep?

The list of Red Sox free agents includes Kenley Jansen, Nick Pivetta, James Paxton, Chris Martin, Tyler O’Neill, Danny Jansen, Luis Garcia and Lucas Sims. 

Jansen is highly likely to leave, with Liam Hendriks set to take over in the late innings. Paxton is set to retire after the season. Perhaps the Red Sox could look to keep O’Neill or Jansen, but both are likely to hit free agency – especially O’Neill, who is represented by Scott Boras.