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Throughout the offseason the CBS Sports MLB experts will bring you a weekly Batting Around roundtable breaking down pretty much anything. The latest news, a historical question, thoughts about the future of baseball, all sorts of stuff. Last week we debated whether the Dodgers are the best team in baseball. This week we're going to tackle one of the best free agent starters still available.

Which team most needs Jordan Montgomery? Where do you think he'll sign?

R.J. Anderson: I'll say the Yankees for both. They still need to add a starter this winter after prioritizing their offense during the first half of the offseason. The familiarity with Montgomery can't hurt -- they know what they're getting and they know that his game works within that park and division. It wouldn't be the most exciting move -- certainly not on the level of signing Yoshinobu Yamamoto -- but it's the kind of necessary work that a team serious about returning to the postseason has to make.

Matt Snyder: I'll say the Rangers most need him, as they look to defend their first-ever World Series title. They were heavily reliant on him in the playoffs and the rotation right now has a nearly-34-year-old Nathan Eovaldi followed by Jon Gray, Andrew Heaney, Dane Dunning and Max Scherzer has had back surgery. Jacob deGrom won't be back from Tommy John surgery yet, either. 

As far as where he'll sign, let's go with the Mets swooping in. Montgomery's agent is Scott Boras and he isn't shy about going directly to owner Steve Cohen (it happened with Carlos Correa). And while the Mets aren't going crazy this offseason, adding a reliable veteran to the rotation like Montgomery would be a nice move. 

Dayn Perry: I'll say the Cardinals, although I think it's unlikely they're willing to pay the going rates for Montgomery. St. Louis has already done a lot of work in repairing a rotation that was the main culprit in their deeply disappointing 2023 season, as they've inked Sonny Gray, Kyle Gibson, and Lance Lynn. However, they could still use a front-end upgrade. Nothing emphasizes that point like the reality that right now decline-phase Miles Mikolas is in line to be their No. 2 starter behind Gray. Montgomery would fill that role much better, probably. I'll repeat that the Cardinals probably don't have the appetite for a nine-figure addition to the already rebuilt rotation, but they could use Monty back in St. Louis. 

Mike Axisa: The Yankees probably need him most. Even with Juan Soto (and Alex Verdugo), they're still on the postseason bubble, and signing Montgomery would go a long way to pushing them into October. Every win the Yankees add right now is enormously valuable because of where they sit on the win curve. They're right on the edge of a postseason spot.

As for where Montgomery will sign, I'll go off the board slightly and say the the Cubs. I have no good reason for saying this, mind you. The Cubs have been inactive and they could use another starter -- I really like Jordan Wicks and Javier Assad but I'd rather not pencil both into the Opening Day rotation -- and Montgomery is in their price range. The "Dansby Swanson, not Trea Turner" price range, if you catch my drift. We haven't had a good surprise signing yet this offseason. We're overdue. I think Montgomery to the Cubs would qualify as a surprise at this point.