Where Will Jack Flaherty End Up?

If there’s been one defining characteristic of the 2024-25 offseason so far (aside from Juan Soto’s record-shattering contract), it’s that the market for starting pitching has been extremely robust. On the heels of a 2023-24 offseason that saw top-of-the-market arms like Blake Snell and Jordan Montgomery linger on the market until the calendar flipped to March, right-hander Michael Wacha kicked things off by re-upping with the Royals before free agency started and the pace hasn’t slowed down much since then. After right-hander Corbin Burnes reached a deal with the Diamondbacks in the final days of December, nearly every notable starting pitcher was already off the market by the time the calendar flipped to January.

Perhaps the biggest exception to that is right-hander Jack Flaherty, who MLBTR ranked as the offseason’s #8 free agent (fourth among starters) at the outset of the winter as part of our annual Top 50 MLB Free Agents list. At the time, we predicted Flaherty would land a five-year, $115MM pact in free agency. That prediction at least seems to have ended up in the right ballpark, as Flaherty is reportedly seeking a five-year deal at this stage of his free agency. Between the winter’s robust market for pitching and the fact that Flaherty was able to reach free agency unencumbered by a Qualifying Offer thanks to a midseason trade from the Tigers to the Dodgers, it stands to reason that he should have a strong chance of reaching that sort of deal.

On the other hand, however, it’s worth noting that there are some signs the market for pitching has begun to cool. Burnes’s deal with Arizona just before the New Year came with a strong average annual value and a potentially lucrative opt-out clause after the second year, but the deferred money involved in the deal reportedly knocks the net present value of the pact below $200MM. MLBTR predicted a seven-year, $200MM pact for Burnes at the outset of the winter, so while even that diminished net present value is more-or-less in line with expectations headed into the offseason, the deal in some ways pales in comparison to the one signed by Max Fried earlier in the winter and certainly falls short of the righty’s reported asking price of $245MM.

If the market for starters has indeed begun to cool somewhat, it’s possible that the market for Flaherty could start to fizzle out when the start of Spring Training games draws near. After all, we need only look back at Montgomery and Snell last winter to see how a pitcher’s market can collapse once they don’t have enough time left to have a typical Spring Training. For now, however, Flaherty still seems to enjoy a fairly robust market. The Blue Jays, Giants, Cubs, Tigers and Oroles have all been connected to the right-hander in recent days.

The Blue Jays and Giants have both been connected to the majority of the offseason’s high-end free agents, as neither club has been particularly shy about its desire to land impact talent this winter. Toronto was notably among the apparent finalists for Burnes before he signed in Arizona, and while the Giants were also strongly connected to Burnes there’s been some indications in the aftermath of his deal with the Diamondbacks that San Francisco is more focused on offense than pitching. Given that the Giants have been attached to first baseman Pete Alonso, it’s possible that the club’s interest in a pitcher of Flaherty’s caliber is more as a backup plan in case they find themselves unable to land the big bat they desire. There’s a possibility that a similar situation could play out with the Blue Jays, as well. The club is known to have extended an offer to outfielder Anthony Santander already, and reporting earlier this winter suggested that Toronto may only have room for one significant multi-year deal in the budget.

It’s possible that the Tigers fall into a similar boat. While the club certainly has the payroll flexibility to make multiple significant multi-year additions if they so desire, president of baseball operations Scott Harris has seemed to be hesitant about making significant multi-year commitments this winter, instead opting to land Alex Cobb and Gleyber Torres on one-year deals. That hasn’t stopped them from engaging in the markets of some big-time free agents, but with Tarik Skubal and Reese Olson helping to anchor a young rotation it’s easy to imaging the club prioritizing a hitter if they decide to offer a nine-figure deal to a player this winter. To that end, Detroit has been one of the teams most frequently connected to third baseman Alex Bregman and also appears to be in the mix for Santander.

Two clubs that have been generally focused on pitching upgrades this winter are the Orioles and the Cubs. Baltimore has already added Tomoyuki Sugano and Charlie Morton to its rotation this winter, and those additions have left them with a deep group of potential starters that isn’t in desperate need of another arm. With that being said, neither Sugano nor Morton can be expected to replace Burnes as the ace of the staff, and with 2023’s staff ace Kyle Bradish expected to miss at least the first half of 2025 it’s fair to think the club would benefit from adding a player of Flaherty’s caliber. To that end, they’ve seemingly remained on the periphery of his market as they continue their search for upgrades even after last week’s deal for Morton.

As for Chicago, they in some ways appear to be the best fit for Flaherty’s services. The Cubs appear to be mostly set on offense after adding Kyle Tucker and Carson Kelly; while there’s potentially room at third base for another bat, they haven’t been closely connected to Alex Bregman in free agency given the presence of top prospect Matt Shaw as a potential Opening Day starter at the position. There’s been plenty of buzz about them adding to their pitching staff, however, and Sahadev Sharma of The Athletic recently described another rotation addition as “inevitable” for the club, whether that’s a move to improve depth or bringing a more impactful piece into the fold. Flaherty would certainly fall into the latter category, but it’s worth noting that Sharma reported earlier this winter that while the Cubs have engaged with Flaherty, they were feeling a bit squeamish about his asking price at that point.

There’s some incentive for Flaherty to wait at least a little longer before making his decision: the presence of right-hander Roki Sasaki on the market. Sasaki is being pursued by a large number of teams and is rumored to have met with at least two Flaherty suitors: the Giants and Cubs. Given his unique situation as a potential front-of-the-rotation piece who can be had for nothing more than a minor league deal (and a hefty portion of a club’s international bonus pool), it’s easy to imagine a number of pitching-hungry clubs focusing their attention squarely on Sasaki while he’s available. The right-hander’s decision is due by January 23, so it’s not hard to imagine Flaherty waiting for that date in case a club that misses out on Sasaki either steps up their offer or enters the fray as a new potential suitor.

In the meantime, how do you think Flaherty’s free agency will play out? Will he land with one of his currently known suitors, or will a “mystery team” swoop in and get a deal done? Is the right-hander going to land a deal within the ballpark of MLBTR’s prediction? Will he fall short of, or perhaps exceed, expectations? Have your say in the polls below.