A Contract Structure That Could Bring Free Agent Jack Flaherty to Brewers

The deal Jack Flaherty hoped he might find in free agency. There were concerns about his back at the trade deadline, nixing a trade to the Yankees, and some teams still seem to harbor those worries. Despite whatever lingering trouble there might be with that back, though, he did take the ball 28 times, pitch 162 innings, strike out 29.9% of opposing batters, and maintain a 3.17 ERA in 2024, and then he pitched well into October, helping the Dodgers beat the Yankees and secure their first full-season World Series championship since 1988. Entering the offseason, MLB Trade Rumors projected that he would command a five-year deal worth $115 million, and ranked him as the eighth-best player in the free-agent class.

According to a source who has monitored Flaherty's market, a deal like that one is "totally out of the question" at this late stage of the hot stove, with February looming in just a few days. A three-year deal in line with those secured at the front end of the offseason by Yusei Kikuchi ($63 million) and Luis Severino ($67 million) is more realistic, but Flaherty, 29, might prefer a different, more flexible structure than those. That makes him a possible target for the Brewers, who have a bit more money to spend and could use more stability at the front end of their rotation.

One version of a deal uniting Flaherty and Chris Hook could look like this:

• $15 million in 2025
• A $25-million player option for 2026, with a $5-million buyout

The Brewers can't spend much more than that $15 million figure for this season, without moving other money off their roster, which would make this style of deal somewhat appealing for them. It would, in effect, be a two-year, $40-million deal, not unlike the one-year, $25-million deal (with an attainable vesting option that ended up being worth $22.5 million) signed by Jordan Montgomery on the eve of Opening Day last winter. Flaherty has some features of interest to make him more exciting than Montgomery, but he hasn't been anywhere near as durable and was not as consistent in his postseason platform campaign as Montgomery was. His deal would have a lower ceiling but a higher floor than Montgomery's.

From the Brewers' side, such a deal would carry a couple facets of appeal. Flaherty has never made more than $14 million in a season or been given a qualifying offer, and thus, they can make him that offer even if he opts out after 2025. In any case in which Flaherty turned down the option, it would be unlikely that he accepts a qualifying offer, because that would only mark a small salary increase relative to the option and be a one-year deal. If he did opt out and walked away, the Crew would be able to pocket a draft pick.

If, on the other hand, Flaherty gets hurt or struggles in 2025 and elects to stick around for 2026, the Crew might well be happy to have him, anyway. They're likely to trade Freddy Peralta next winter, as they have Corbin Burnes and Devin Williams the last two offseasons. Aaron Civale and Nestor Cortes will both become free agents in the fall, and Brandon Woodruff's mutual option for 2026 is unlikely to be picked up, because all mutual options are unlikely to be picked up. Although the Crew have young pitchers set to take on larger roles this year and next (like Aaron Ashby, Rober Gasser, DL Hall, Logan Henderson, and Tobias Myers), they could use a veteran for 2026, and Flaherty being that guy might be fine, even if it means he had a poor 2025 that discouraged him from returning to the market.

Not unlike Peralta, Flaherty is a relatively low-slot guy with deceptive carry on his four-seamer and two distinct breaking balls. He does a lot of things the Brewers like, which is why they had serious interest in him before pivoting to Frankie Montas at the trade deadline. On the right kind of deal, these two parties might make perfect partners this year, just as the Brewers and Rhys Hoskins did last January. It would be a boon to the roster in its own right, and could also open the door for another move, like trading Civale to a pitching-needy team for infield help.