MLB Free Agency Predictions 2026: Picking Landing Spots for Top 10 Pitchers this Winter
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- MLB Free Agency Predictions 2026: Picking Landing Spots for Top 10 Pitchers this Winter
While the 2026 MLB offseason has a looming lockout hanging over it, this winter should also deliver a free-agency frenzy for the top talent available. The Milwaukee Brewers just demonstrated how important great starting pitching can be when it comes to winning it all and a market that features the likes of Tarik Skubal and Freddy Peralta should lead to a massive spending splurge with movement around the league.
Read More: 2027 MLB Power Rankings
Let’s dive into our MLB free agency predictions for the 10 best pitchers on the market this winter.
The Chicago Cubs and Los Angeles Dodgers seem to be viewed as the co-favorites to land Tarik Skubal. Both are viable possibilities, but we think the pursuit of the two-time AL Cy Young Award winner ends in a surprise. With all of the young, cost-controlled talent on the St. Louis Cardinals roster, Chaim Bloom has greater flexibility to spend on a true ace. Adding Skubal to the front of the Cardinals’ rotation would solve their biggest need and buy time for their young arms to be brought along slowly and develop. Adding Skubal is the perfect way for St. Louis to thrust itself back into the chase and demonstrate that it’s also ready to spend money again.
This is another one of our MLB free agency predictions that probably goes against the grain. The thing is, the Tampa Bay Rays are likely well-aware that something resembling a salary floor is coming to Major League Baseball, and an eventual new stadium offers even more incentive to invest more money into the roster. Let’s also not forget that Freddy Peralta thrived in Tampa Bay (3.25 ERA and 1.01 WHIP in regular season), and he credited the organization for helping him get things back on track. While it seems clear many around baseball would be surprised if Peralta remains in Tampa Bay, we’re willing to predict that it happens.
It’s time for the Washington Nationals to splurge in MLB free agency. The Nationals lineup produced the third-most runs in baseball (821) this past season but finished 77-85, almost entirely because of a Nationals rotation that recorded the fourth-fewest quality starts (36) in baseball. Trevor Rogers is a great solution. Hitting the open market at 29 years old, Rogers boasts a 3.16 ERA with a 1.07 WHIP across his last 48 starts. Washington can plug him in as its No. 2 starter behind Cade Cavalli, pushing Connelly Early into a No. 3 role that he feels more well-suited for coming off elbow troubles in 2026. Plus, Rogers’ price range would still allow Washington to add a back-end starter or high-end reliever.
The Chicago White Sox’s unexpected success was great to see, but if the rotation isn’t addressed this winter, we feel it could prove to be an outlier. Chicago had one of the highest strikeout rates in baseball with a pitching staff that finished 28th in quality starts (34) and 19th in WHIP (1.31). That’s not a recipe for sustained success. Fortunately for Chicago, it has financial flexibility this offseason in a market offering an array of front-line starters. For 31-year-old Michael King, this will probably be his last chance to cash in. We think the White Sox put the biggest offer on the table, adding King as the face of their rotation with Sean Burke, Davis Martin, and Hagen Smith behind him.
Sonny Gray likely only has another season or two left before he calls it a career. Given that he spent a fair amount of time this past season flying back home to be with his family in Nashville, it stands to reason he’ll prioritize distance from home when choosing his next club. It’s a short flight from Atlanta to Nashville and the Braves’ organization would likely prefer landing a starting pitcher that it can sign to a short-term contract with a higher annual average value. The fit seems perfect on paper and this would be one of our MLB free agency predictions that we have the highest level of confidence in making.
The New York Mets will feel obligated to do something, even with high expectations for Nolan McLean and Christian Scott in 2027. Kevin Gausman, who turns 36 in January, would probably be best suited to serve as a No. 2 starter, and that spot is available in New York. Because of his age, Gausman is likely going to take a two- or three-year deal, meaning the Mets could have his contract, along with Bo Bichette’s deal, off the books in 2029.
Kaima Taira, a 26-year-old starter who posted the lowest ERA in Japan (1.36) this past season, was just posted for bidding by the Seibu Lions. The New York Yankees will certainly be interested in him, along with other clubs, but we see the Toronto Blue Jays coming out on top of the bidding war for another Japanese talent. Toronto could plug him in as its No. 3 starter behind Dylan Cease and José Soriano, pushing Cody Ponce (coming off an ACL tear) into the No. 5 role.
The San Francisco Giants will probably be linked to bigger names in MLB free agency, but we’ve seen enough reporting on ownership to be skeptical about that level of financial commitment being made. San Francisco desperately needs quality starters, but we’re inclined to believe it will pursue more cost-effective options. Enter Foster Griffin, age 31, who earned his first All-Star selection this past season after registering a 3.60 ERA in 31 starts with the Washington Nationals and Cleveland Guardians. Griffin’s lack of success in the majors until 2026, paired with his age, should lower both his asking price and the number of years he’ll be offered. That makes him an ideal fit for San Francisco.
We’re certainly not going to predict that the Chicago Cubs come out of MLB free agency empty-handed. After seeing the success Milwaukee had with a dominant bullpen, Chicago might try and take a bit of a similar approach to its roster construction. Adrian Morejon registered a 2.58 ERA with a 248-66 K-BB ratio across 223.1 innings from 2024-26; he is one of the best left-handed relievers in baseball. The Cubs can splurge on him, potentially acquire a front-line starter on the trade market, and still have money to spend on other areas of need.
With Trevor Rogers potentially departing, it would be wise for the Baltimore Orioles to find another veteran who could provide some stability for their rotation. Clay Holmes, an All-Star selection in 2022 and 2024, will be entering his age-34 season. He excelled with the Mets (2.39 ERA in nine starts) last season and boasts a career 3.44 ERA across the last two years, covering 267 innings. Baltimore could bring him in as its third starter next season, signing him to a two-year deal with an option for 2029, and it could get similar results to what Rogers put up this past season.
MLB Free Agency Predictions 2026: Picking Landing Spots for Top 10 Pitchers this Winter
MLB Free Agency Predictions 2026: Picking Landing Spots for Top 10 Pitchers this Winter
MLB Free Agency Predictions 2026: Picking Landing Spots for Top 10 Pitchers this Winter
MLB Free Agency Predictions 2026: Picking Landing Spots for Top 10 Pitchers this Winter
MLB Free Agency Predictions 2026: Picking Landing Spots for Top 10 Pitchers this Winter
MLB Free Agency Predictions 2026: Picking Landing Spots for Top 10 Pitchers this Winter
MLB Free Agency Predictions 2026: Picking Landing Spots for Top 10 Pitchers this Winter
MLB Free Agency Predictions 2026: Picking Landing Spots for Top 10 Pitchers this Winter
MLB Free Agency Predictions 2026: Picking Landing Spots for Top 10 Pitchers this Winter
MLB Free Agency Predictions 2026: Picking Landing Spots for Top 10 Pitchers this Winter
MLB Free Agency Predictions 2026: Picking Landing Spots for Top 10 Pitchers this Winter
MLB Free Agency Predictions 2026: Picking Landing Spots for Top 10 Pitchers this Winter
MLB Free Agency Predictions 2026: Picking Landing Spots for Top 10 Pitchers this Winter
While the 2026 MLB offseason has a looming lockout hanging over it, this winter should also deliver a free-agency frenzy for the top talent available. The Milwaukee Brewers just demonstrated how important great starting pitching can be when it comes to winning it all and a market that features the likes of Tarik Skubal and Freddy Peralta should lead to a massive spending splurge with movement around the league.
Read More: 2027 MLB Power Rankings
Let’s dive into our MLB free agency predictions for the 10 best pitchers on the market this winter.
Tarik Skubal: St. Louis Cardinals
The Chicago Cubs and Los Angeles Dodgers seem to be viewed as the co-favorites to land Tarik Skubal. Both are viable possibilities, but we think the pursuit of the two-time AL Cy Young Award winner ends in a surprise. With all of the young, cost-controlled talent on the St. Louis Cardinals roster, Chaim Bloom has greater flexibility to spend on a true ace. Adding Skubal to the front of the Cardinals’ rotation would solve their biggest need and buy time for their young arms to be brought along slowly and develop. Adding Skubal is the perfect way for St. Louis to thrust itself back into the chase and demonstrate that it’s also ready to spend money again.
Freddy Peralta: Tampa Bay Rays
This is another one of our MLB free agency predictions that probably goes against the grain. The thing is, the Tampa Bay Rays are likely well-aware that something resembling a salary floor is coming to Major League Baseball, and an eventual new stadium offers even more incentive to invest more money into the roster. Let’s also not forget that Freddy Peralta thrived in Tampa Bay (3.25 ERA and 1.01 WHIP in regular season), and he credited the organization for helping him get things back on track. While it seems clear many around baseball would be surprised if Peralta remains in Tampa Bay, we’re willing to predict that it happens.
Trevor Rogers: Washington Nationals
It’s time for the Washington Nationals to splurge in MLB free agency. The Nationals lineup produced the third-most runs in baseball (821) this past season but finished 77-85, almost entirely because of a Nationals rotation that recorded the fourth-fewest quality starts (36) in baseball. Trevor Rogers is a great solution. Hitting the open market at 29 years old, Rogers boasts a 3.16 ERA with a 1.07 WHIP across his last 48 starts. Washington can plug him in as its No. 2 starter behind Cade Cavalli, pushing Connelly Early into a No. 3 role that he feels more well-suited for coming off elbow troubles in 2026. Plus, Rogers’ price range would still allow Washington to add a back-end starter or high-end reliever.
Michael King: Chicago White Sox
The Chicago White Sox’s unexpected success was great to see, but if the rotation isn’t addressed this winter, we feel it could prove to be an outlier. Chicago had one of the highest strikeout rates in baseball with a pitching staff that finished 28th in quality starts (34) and 19th in WHIP (1.31). That’s not a recipe for sustained success. Fortunately for Chicago, it has financial flexibility this offseason in a market offering an array of front-line starters. For 31-year-old Michael King, this will probably be his last chance to cash in. We think the White Sox put the biggest offer on the table, adding King as the face of their rotation with Sean Burke, Davis Martin, and Hagen Smith behind him.
Sonny Gray: Atlanta Braves
Sonny Gray likely only has another season or two left before he calls it a career. Given that he spent a fair amount of time this past season flying back home to be with his family in Nashville, it stands to reason he’ll prioritize distance from home when choosing his next club. It’s a short flight from Atlanta to Nashville and the Braves’ organization would likely prefer landing a starting pitcher that it can sign to a short-term contract with a higher annual average value. The fit seems perfect on paper and this would be one of our MLB free agency predictions that we have the highest level of confidence in making.
Kevin Gausman: New York Mets
The New York Mets will feel obligated to do something, even with high expectations for Nolan McLean and Christian Scott in 2027. Kevin Gausman, who turns 36 in January, would probably be best suited to serve as a No. 2 starter, and that spot is available in New York. Because of his age, Gausman is likely going to take a two- or three-year deal, meaning the Mets could have his contract, along with Bo Bichette’s deal, off the books in 2029.
Kaima Tairia: Toronto Blue Jays
Kaima Taira, a 26-year-old starter who posted the lowest ERA in Japan (1.36) this past season, was just posted for bidding by the Seibu Lions. The New York Yankees will certainly be interested in him, along with other clubs, but we see the Toronto Blue Jays coming out on top of the bidding war for another Japanese talent. Toronto could plug him in as its No. 3 starter behind Dylan Cease and José Soriano, pushing Cody Ponce (coming off an ACL tear) into the No. 5 role.
Foster Griffin: San Francisco Giants
The San Francisco Giants will probably be linked to bigger names in MLB free agency, but we’ve seen enough reporting on ownership to be skeptical about that level of financial commitment being made. San Francisco desperately needs quality starters, but we’re inclined to believe it will pursue more cost-effective options. Enter Foster Griffin, age 31, who earned his first All-Star selection this past season after registering a 3.60 ERA in 31 starts with the Washington Nationals and Cleveland Guardians. Griffin’s lack of success in the majors until 2026, paired with his age, should lower both his asking price and the number of years he’ll be offered. That makes him an ideal fit for San Francisco.
Adrian Morejon: Chicago Cubs
We’re certainly not going to predict that the Chicago Cubs come out of MLB free agency empty-handed. After seeing the success Milwaukee had with a dominant bullpen, Chicago might try and take a bit of a similar approach to its roster construction. Adrian Morejon registered a 2.58 ERA with a 248-66 K-BB ratio across 223.1 innings from 2024-26; he is one of the best left-handed relievers in baseball. The Cubs can splurge on him, potentially acquire a front-line starter on the trade market, and still have money to spend on other areas of need.
Clay Holmes: Baltimore Orioles
With Trevor Rogers potentially departing, it would be wise for the Baltimore Orioles to find another veteran who could provide some stability for their rotation. Clay Holmes, an All-Star selection in 2022 and 2024, will be entering his age-34 season. He excelled with the Mets (2.39 ERA in nine starts) last season and boasts a career 3.44 ERA across the last two years, covering 267 innings. Baltimore could bring him in as its third starter next season, signing him to a two-year deal with an option for 2029, and it could get similar results to what Rogers put up this past season.
