Why one MLB insider would bet Red Sox’s Alex Cora hits free agency

The Red Sox will enter the 2024 season with Alex Cora’s future looming large over the franchise. The manager is entering the final year of his contract and has not yet had substantive talks with the club about an extension, meaning there’s a real chance the sides part ways after the year.

Complicating things further is the fact that Craig Counsell, who bolted the Brewers for the Cubs and signed a record-setting five-year, $40 million contract once his contract in Milwaukee ended last fall, changed the game for managers by testing free agency (a new concept for those in the role) and choosing the best offer. There have already been reports that multiple teams have interest in hiring Cora, who unlike Counsell has won a World Series ring as a manager, for 2025 and beyond.

On Wednesday’s Fenway Rundown podcast, MLB insider Ken Rosenthal (from The Athletic and FOX Sports) said he believes Cora’s future largely depends on how the Red Sox play in 2024.

“It depends on the season, I would imagine,” Rosenthal said. “If the Red Sox are successful and they offer him a good extension, I would think he stays. I believe Alex Cora feels a sense of loyalty to this ownership for sticking with him after he was suspended for a year (in 2020). They brought him back, and they didn’t have to do that. In fact, some people were surprised they did that. I’m fairly certain that Alex Cora won’t forget that, that if this situation is working well, as long as he’s going good with (Craig) Breslow and things are going smoothly and the team is successful, then an extension could very well be the likely outcome here.

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“If the season doesn’t go as well, if he doesn’t jive with Breslow the way he would want, or maybe the way Breslow would want, then certainly, we could be looking at free agency. I don’t know that Cora, if they’re coming off a losing season, will be as highly regarded as Counsell... but I can see a similar scenario playing out for Cora.

“If I had to bet, I’d bet he’d become a free agent. Because why not, right? When a player is a year away, the player wants to become a free agent. A manager is no different.”

Cora, who is 440-370 (.543) in five non-consecutive seasons (2018-19, 2021-23) is widely regarded as one of the best managers in baseball despite the Red Sox finishing in last place in each of the last two seasons. The 48-year-old is well-connected throughout the game and keeps close tabs on other organizations. At Boston’s Winter Weekend event earlier this month, he acknowledged that Counsell’s record-setting deal was “great” for the managerial trade. In recent months, he has made it no secret that the possibility of getting a similar (or better) deal from a club excites him.

New chief baseball officer Craig Breslow did not give Cora an extension after being hired so the plan appears to be to see how 2024 goes before assessing the manager’s future. Theoretically, Cora could leave no matter how the Red Sox play. If the club plays well, he could capitalize on a winning season by hitting free agency with peak value. If the club does not contend, as many expect, he could be cut loose and forced into finding work elsewhere as a result.

Rosenthal believes Cora’s value will be tied to Boston’s on-field play and that there would be many teams interested in him if he hits the open market. An eight-figure deal of at least $10 million per year is even plausible.

“I don’t see why it would be out of the question,” Rosenthal said. “Let’s say they have a great year, that they go to the ALCS or World Series, just for the sake of discussion. I know it’s not likely based on everything else we’ve discussed, but let’s say that happens. Then he’s a hot free agent.

Why wouldn’t you pay your manager that when you’re paying players who aren’t nearly as impactful that kind of amount? I know teams don’t want to mess with the structure and screw up things for one another, but guess what? The Cubs just did. And another team might for Cora, especially a team like the Dodgers or the Yankees that have greater resources.

“It depends on this year. If they don’t have a good year, his value starts to diminish a little bit. He’s been part of these teams that have lost. Now, I don’t blame him for that, but he is the manager.”