Free agent righty Jack Flaherty appeared on the Foul Territory podcast recently to discuss his ongoing trip through free agency and made some revealing comments about the state of his market. Notably, the right-hander indicated that while a handful of teams have continued to check in with him throughout the offseason, clubs have been reluctant to make him a formal offer to this point.
“It’s like, ’What are you up to?’ [and] ’When is the market gonna move?’… You have to make an offer and then it’ll go, but just calling and checking in… I don’t know. It’s weird,” Flaherty said. He then went on to suggest that clubs might have some level of complacency about improving beyond the level needed to have a chance at getting into the playoffs.
“It’s not that I don’t think teams want to win, I just think you have a lot of teams that look at their rosters and they’re happy with it… teams just want to get into the playoffs. Maybe it’s not World Series or bust, it’s just hope we can get into the playoffs and then kind of see what happens.”
Since the league expanded the postseason to include 12 teams back in 2022, there’s been a trend away from the tear-down method of rebuilding used by teams like the Cubs, Nationals, and Orioles in recent years. Entering the 2025 season, only the White Sox and Marlins are rebuilding in that sort of aggressive fashion with the rest of the league’s clubs generally looking to maintain at least some level of baseline competitiveness. That’s a strategy incentivized by the new playoff format, which not only added another playoff team in both leagues but also allows Wild Card teams to participate in a three-game series rather than the one-game, win-or-go-home playoff the 10-team format utilized in the past.
That guarantee of a postseason series for any club that can make the playoffs at all, when combined with the inherit randomness of baseball’s playoffs, has arguably weakened the incentive for teams to maximize their odds of winning their division at the expense of the franchise’s longer-term outlook. Some evidence for this is relatively easy to see: 2024 was the first season in a decade where no club won 100 games, and the first three seasons of the 12-team playoff format have seen five teams that won 86 games or less make the postseason after just two such teams made the playoffs during the entire 10-team playoff era that spanned from 2012 to 2021.
That includes 84-win campaigns by the Diamondbacks and Marlins in 2023, which were tied for the lowest win total for any playoff team since 83-win Cardinals won the World Series back in 2006. Only one other team, the 2005 Padres, has made it to the playoffs with less than 84 wins in a 162-game season since the 1973 Mets won the AL East with 82 wins. To what extent that increased ability for teams with win totals in the mid-80’s to make the postseason can be traced back to the struggles some higher-end free agents such as Flaherty have faced in finding free agent deals that are commensurate with their perceived value is difficult to pin down, however.
Regardless of the cause of Flaherty’s depressed market, it was reported earlier this month that the right-hander is now open to short-term offers as he looks to find his new home with the start of Spring Training just two over two weeks away. The Tigers, Cubs, Orioles, and Blue Jays are among the teams that have been connected to Flaherty this winter. The right-hander expressed a desire to return to the Dodgers early in the offseason, but that door has long appeared closed in the aftermath of Los Angeles striking early to sign Blake Snell back in November. The Dodgers have also added Roki Sasaki since then, further crowding their rotation mix. Flaherty acknowledged the long odds of a reunion during the interview, noting that he “can do the math” and surmise that he’s “most likely” not returning to LA. He also has interest in returning to his other 2024 club this year, however, and spoke positively of the Tigers during the interview.
“You know, I wanted to stay in Detroit,” Flaherty said. “We had conversations, and I loved it there. And I thought the combo of me and Skub was incredible… we’ve been talking to them and talking to other teams… Hey, you know, it would be fun to go back there.”
The Tigers appear to be one of the more active teams at the top of the remaining free agent market at this point, as they’ve remained engaged not only with Flaherty but also with third baseman Alex Bregman. Bregman has appeared to be the club’s priority to this point, but those are reportedly at a “standstill.” If Bregman ultimately signs elsewhere, it’s easy to imagine Detroit redirecting those funds to Flaherty where the righty would reclaim his role at the top of the club’s rotation alongside Tarik Skubal. That signing would push the club’s potential fifth starter options like Kenta Maeda, Matt Manning, Casey Mize, and Keider Montero into depth roles entering the season.