Red Sox Reportedly Looking to Shed Payroll Prior to Additional FA Pursuits

This might not seem like a Cubs-related topic on the surface, but bear with me for a little while and we’ll get there. The Red Sox made a small splash by signing Lucas Giolito to a two-year, $38.5 million deal on Friday, then made a big splash by trading Chris Sale and cash to the Braves for infielder Vaughn Grissom less than 24 hours later. What is it with Sox teams and making deals involving those two pitchers? Former Cubs pitching director and AGM Craig Breslow still needs to fill out his rotation, but he may need to free up more money to do it.

According to Chris Cotillo of, “the Red Sox have told at least one free agent target that they need to shed more payroll before pursuing him as aggressively as they want to.” This after they saved an estimated $3-4 million by trading Alex Verdugo for Tyler O’Neill and nearly $9 million of Sale’s AAV hit (they’re paying $17M of his $27.5M actual salary) to get them to around $193.5 million in 2024 CBT payroll.

That’s more than $43 million below the first tax penalty threshold and roughly $30 million less than their 2023 payroll, so it’s pretty odd to think they’d need to cut deeper. Unless, that is, Breslow has a mandate from ownership to remain under a certain figure. Let’s say it’s $225 million, which tracks pretty well if the Red Sox are talking with either Jordan Montgomery or Blake Snell.

They’re the betting favorites for Montgomery, who’s been projected to get a $25 million-ish AAV, so signing him would give Breslow just $6.5 million in breathing room based on my hypothetical ceiling. The Cubs aren’t alone in their philosophy on maintaining a buffer, but it makes sense that Breslow would want to leave room for midseason additions if Boston’s budget is being handled the same way as what he was used to in Chicago. That would also help to explain why the Sox hired a baseball boss with little to no real experience running an organization.

Speaking of the Cubs, they still have yet to add an MLB contract to their 40-man roster this offseason. As conservative as Jed Hoyer is when it comes to free agency, this may provide an opportunity to swoop in a get a deal done. I’m making more than one supposition here, of course, not the least of which is that the report about the Red Sox effectively waiting for payday is accurate.

I’m also guessing that Montgomery is the free agent in question — the report said “at least one,” so there could certainly be others — and that the Cubs are indeed interested in him. The flip side to this is that Scott Boras represents Montgomery and several other top available free agents, and one thing we know about the super-agent’s MO is that he’s more than willing to wait on the right deal. He won’t pivot from the Red Sox just because they want to wait. In fact, he might prefer that because it allows him to exert even more leverage.

We’ve reached the point in the offseason where the massive deals are done and now it’s all about wrangling both publicly and behind closed doors to find value. Maybe this whole report is just a matter of Boras chumming the waters and getting other teams to step up their offers, which I think is entirely possible. He’s certainly not been shy about calling the Cubs out this winter or in the past.

With the new year right around the corner and spring training not far behind, there are still plenty of available players out there. Maybe that means all this waiting will pay off in a flurry of moves as Hoyer sets up for some big CubsCon announcements. Or, you know, maybe they all get strung out and we’re still waiting on deals to trickle in even after pitchers and catchers have reported.

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