Key Points
Bullet point summary by AI
- With a deep pitching market looming, teams are already preparing for a potential record-breaking contract for an elite starter this winter.
- Two dominant pitchers from Detroit and New York are expected to reset market values, with one likely to leave his current team in free agency.
- The upcoming free agent class may see teams prioritize long-term stability before a potential work stoppage, impacting contract strategies across the league.
This past winter, MLB free agency featured names like Kyle Tucker, Kyle Schwarber, Pete Alonso, Bo Bichette, Alex Bregman and Cody Bellinger. It was not a deep class, but there was plenty of high-end talent, and some of baseball’s best names are now playing in new cities.
The upcoming free agent class in baseball, however, is not as deep; it is incredibly unlikely that any player tops Tucker’s $60 million annual average value from this past season. But it's also extremely likely that a new record will be broken for the largest contract ever for a free agent pitcher, a mark currently held by Yoshinobu Yamamoto on his 12-year, $325 million contract with the Los Angeles Dodgers.
There's still a lot of baseball to played, and a lot of money to be earned or lost, but it's never too early to look ahead at how this winter might reshape the landscape of the league. Who are some of the best players available? Let’s dive in.
LHP Tarik Skubal, Detroit Tigers
This is the big one. Skubal will land an absolutely mammoth contract in free agency and is primed to reset the market for elite starters. The 29-year-old is coming off two dominant seasons in Detroit, posting a 2.39 ERA in 31 starts in 2024 and a 2.21 ERA in 31 starts in 2025. He’s off to another strong start this season, with a 2.55 ERA in his first three outings.
It’s very likely that he’ll leave the Tigers in free agency. Framber Valdez was signed to the richest contract in the Scott Harris era, and he’ll serve as a natural replacement for Skubal moving forward. Detroit will try to retain Skubal, of course, but the strong likelihood is that he heads elsewhere.
RHP Freddy Peralta, New York Mets
I was around Peralta a lot in Milwaukee, and watching him grow as a person, father, leader and pitcher was eye-opening. Moving him to Queens was one of the hardest things that the Brewers front office has done, and it’s no surprise that the person who acquired him with the Mets, David Stearns, was responsible for bringing Peralta to Milwaukee in the first place. Stearns loves Peralta.
Still, an extension was a long shot before Opening Day. He feels primed to play out the final year of his contract and become a free agent, and MLB Trade Rumors mentions that his profile lines up with a similarly electric if occasionally maddening righty in Dylan Cease — who just signed a seven-year, $210 million contract. Peralta prefers a long-term deal, and if he pitches similarly to how he did in Milwaukee, he should have no shortage of options.
INF Bo Bichette, New York Mets
To clarify: Bichette is not currently scheduled to become a free agent after the 2026 season, but he has the ability to opt out of his three-year deal with the New York Mets. Hence his inclusion on this list.
This winter, Bichette had a widespread market. The Phillies thought they were signing the All-Star slugger to a $200+ million contract before their division rivals swooped in at the 11th hour. The Boston Red Sox had significant interest. There were others involved as well.
If Bichette opts out, that means he had a strong season and can use that to get the sort of long-term deal he's looking for. If he underperforms, he can opt into the second year of his current contract and earn $55.3 million in 2027. Pretty smart business.
2B Jazz Chisholm Jr., New York Yankees
Chisholm is a player with elite traits and is the best non-pitcher on the market unless Bichette opts out of his contract. He hit a career-high 31 home runs and was one of seven players to go 30-30 last season. He does come with some questions — he’s a career .246/.315/.450 hitter with 108 home runs and 311 RBI in seven seasons — but the upside here will catch many teams’ attention.
I expect him to land a contract in excess of $100 million, and Nico Hoerner landing a $141 million extension should only help Chisholm and his camp come free agency.
RHP Michael King, San Diego Padres
Like Bichette, King isn’t technically a free agent after the 2026 season. He can opt out of a three-year, $75 million contract though, and if he stays healthy he should be a strong candidate to land a longer-term deal in free agency.
When healthy, King is one of the better pitchers in baseball. In 2024, he posted a 2.95 ERA and 201 strikeouts in 31 games. In 15 games last season, he posted a 3.44 ERA. Health is the big “if” with King. And if he manages to stay healthy in 2026, a contract worth over $100 million should easily be attainable for the right-hander.
The rest
The options here include names like Trevor Rogers, Daulton Varsho, Tatsuya Imai (who can opt out after 2026), Seiya Suzuki, Randy Arozarena, Kris Bubic, Bryan Abreu, Zac Gallen and Trent Grisham, among others. Rogers’ turnaround here is noteworthy — in 2024, the trade for him looked like one of baseball’s worst in recent memory, but he’s bounced back and been incredibly dependable for the Baltimore Orioles.
Something to watch next winter will be players wanting to sign before the current collective bargaining agreement expires. The uncertainty that a (seemingly inevitable) lockout brings weighs on players, and they'll want to know where they will suit up and for how much in 2027 and potentially beyond. Just look at Kris Bryant, who waited to sign until after the 2021-2022 lockout, eventually landing with the Colorado Rockies on a $182 million contract. Of course, the money was great. But as Bryant told The Athletic in 2024:
“It’s like, ‘Oh shoot, I need to get there,’” Bryant said, in regards to needing to report to camp and pick a team. “There were other teams interested, but I didn’t want to wait around … It was a completely different situation for a lot of free agents at the time. I guess I didn’t do as much research into the prospects as I could have.”
With a relatively weak free agent class, it remains to be seen exactly how aggressive teams will be in signing tier two and lower players. But it would behoove players to understand what’s coming after this season: a potentially long work stoppage that will have many ups and downs. And signing before that, and not having to worry about a contract and where they’ll play that upcoming season, might be the strategy for most players. Especially after Bryant’s seeming regret of signing in Colorado.