Latest On Jack Flaherty’s Market

Right-hander Jack Flaherty signed a pillow contract with the Tigers last winter, and it went just about as well as anyone could’ve reasonably hoped. The right-hander dominated to the tune of a 3.17 ERA in 28 starts with the Tigers and Dodgers and ended in Flaherty hoisting the World Series trophy alongside his teammates in Los Angeles. Now, he’s back on the free agent market and in line for a much more lucrative deal than the $14MM guarantee he landed from Detroit last winter. While the majority of the baseball world has been focused on Corbin Burnes in the days following the Winter Meetings when considering the free agent market for starting pitchers, this evening saw Ken Rosenthal of The Athletic discuss where Flaherty’s market currently stands.

One possibility Rosenthal suggests could be on the table for Flaherty is a reunion with Baltimore. That’s not exactly a surprise, given that a report from Rosenthal himself last week indicated that Baltimore is reluctant to pursue starting pitchers from other clubs encumbered by the Qualifying Offer, who would therefore require the Orioles to forfeit draft capital in order to be signed. While the Orioles’ top target has long been considered to be Burnes, who finished fifth in AL Cy Young award voting during his lone season with Baltimore this past year, Rosenthal suggests that Flaherty stands out as a “fallback option” for the Orioles should they fail to reunite with their current ace.

While Flaherty struggled in his previous stint with Baltimore, which came down the stretch in 2023 and saw him post an ugly 6.75 ERA across 34 2/3 innings of work, Rosenthal notes that Orioles brass understood Flaherty was gassed amid his first full, 162-game season on the mound since 2019. With other top free agents unencumbered by the QO like Blake Snell, Yusei Kikuchi, and Nathan Eovaldi all already off the board, Flaherty stands out as by far the top pitcher available on the free agent market who isn’t attached to the QO. That’s a big reason why MLBTR predicted a five-year, $115MM deal for the right-hander as part of our annual Top 50 MLB Free Agents list, where he ranked eighth.

One other potential player in Flaherty’s market Rosenthal mentions is the Red Sox. While it’s unclear how interested Boston is in Flaherty at the moment, Rosenthal reports that the club “liked” the righty last winter before he signed in Detroit. Naturally, it will take a far more significant financial commitment to land Flaherty this winter than it would’ve last year. That shouldn’t be a problem for Boston, however, as they’ve been heavily involved in the bidding for top free agents such as Juan Soto, Max Fried, and Alex Bregman this winter and reportedly remain in the market for rotation help even after landing ace lefty Garrett Crochet in a trade with the White Sox earlier this week. A rotation fronted by a trio of Crochet, Flaherty, and Tanner Houck would surely be an enticing possibility for the Red Sox, and it’s easy to imagine them having interest in Flaherty if they have money leftover once the sweepstakes for Bregman and Burnes come to an end.

Aside from the Orioles and Red Sox, a handful of teams have been connected to Flaherty so far this winter. The Mets have previously been connected to Flaherty and have at least one opening in a rotation that could use a clear impact starter to pair with Kodai Senga. The Cubs made a big splash to land Kyle Tucker from the Astros yesterday and have remaining involved in the rotation market even after signing Matthew Boyd earlier this winter, though their interest in Flaherty is reportedly dependent on his price tag. The Tigers also apparently have at least some interest in a reunion with Flaherty, though it’s unclear if they’d be willing to outbid other top contenders and have since added veteran righty Alex Cobb to their starting staff.