The 2026 season concluded with the Milwaukee Brewers lifting their first World Series title. MLB teams will now shift their focus to the offseason, particularly to roster changes.
While the 2027 offseason is expected to be dominated by two-time Cy Young winner Tarik Skubal’s free agency, MLB teams could make other blockbuster additions through trades.
Here are 10 bold trades that MLB teams could pursue this offseason.
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#1 Elly De La Cruz to Tampa Bay Rays
” srcset=”https://www.sme-insights.co.uk/wp-content/uploads/2026/10/63dfb-17933629069141-1920.avif?w=190 190w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/63dfb-17933629069141-1920.avif?w=720 720w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/63dfb-17933629069141-1920.avif?w=640 640w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/63dfb-17933629069141-1920.avif?w=1045 1045w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/63dfb-17933629069141-1920.avif?w=1200 1200w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/63dfb-17933629069141-1920.avif?w=1460 1460w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/63dfb-17933629069141-1920.avif?w=1600 1600w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/63dfb-17933629069141-1920.avif 1920w”>Cincinnati Reds infielder Elly De La Cruz is a blockbuster trade candidate for the offseason – Source: Imagn
Cincinnati Reds infielder Elly De La Cruz had a stellar 2026, registering a career-high 30 home runs and 30 steals to mark his first 30-30 season. He is under team control through the 2030 season.
The two-time All-Star reportedly turned down a long-term contract extension last year and has been linked with a trade away from the team. The Tampa Bay Rays, who came up short against the Milwaukee Brewers in the World Series, could make a blockbuster move for the Reds infielder.
#2 Jacob deGrom to Los Angeles Dodgers
” srcset=”https://www.sme-insights.co.uk/wp-content/uploads/2026/10/0b681-17933637086615-1920.avif?w=190 190w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/0b681-17933637086615-1920.avif?w=720 720w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/0b681-17933637086615-1920.avif?w=640 640w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/0b681-17933637086615-1920.avif?w=1045 1045w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/0b681-17933637086615-1920.avif?w=1200 1200w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/0b681-17933637086615-1920.avif?w=1460 1460w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/0b681-17933637086615-1920.avif?w=1600 1600w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/0b681-17933637086615-1920.avif 1920w”>Texas Rangers ace Jacob deGrom could be traded in the offseason – Source: Imagn
The Los Angeles Dodgers have struggled with injuries to their starting pitchers over the last two seasons. Despite a star-studded rotation, the Dodgers are expected to add a starting pitcher in the offseason.
Two-time Cy Young winner Jacob deGrom could be an option for the NL West franchise. He could stabilize the rotation amid the uncertainty surrounding Shohei Ohtani’s return to pitching in 2027.
#3 Mason Miller to Chicago Cubs
” srcset=”https://www.sme-insights.co.uk/wp-content/uploads/2026/10/ca6e6-17933641360562-1920.avif?w=190 190w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/ca6e6-17933641360562-1920.avif?w=720 720w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/ca6e6-17933641360562-1920.avif?w=640 640w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/ca6e6-17933641360562-1920.avif?w=1045 1045w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/ca6e6-17933641360562-1920.avif?w=1200 1200w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/ca6e6-17933641360562-1920.avif?w=1460 1460w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/ca6e6-17933641360562-1920.avif?w=1600 1600w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/ca6e6-17933641360562-1920.avif 1920w”>The San Diego Padres could trade Mason Miller in the offseason – Source: Imagn
The San Diego Padres failed in their pursuit of their first World Series title in 2026. After their postseason exit, All-Star relief pitcher Mason Miller has been linked to a trade away from the NL West franchise.
Miller, one of the league’s most dominant pitchers, has been linked to a move to the Chicago Cubs this offseason. He could be a perfect fit for the Cubs’ brand of baseball.
#4 Jarren Duran to Philadelphia Phillies
” srcset=”https://www.sme-insights.co.uk/wp-content/uploads/2026/10/e7e40-17933649487527-1920.avif?w=190 190w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/e7e40-17933649487527-1920.avif?w=720 720w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/e7e40-17933649487527-1920.avif?w=640 640w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/e7e40-17933649487527-1920.avif?w=1045 1045w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/e7e40-17933649487527-1920.avif?w=1200 1200w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/e7e40-17933649487527-1920.avif?w=1460 1460w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/e7e40-17933649487527-1920.avif?w=1600 1600w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/e7e40-17933649487527-1920.avif 1920w”>Boston Red Sox outfielder Jarren Duran is likely to be traded in the offseason – Source: Imagn
Boston Red Sox outfielder Jarren Duran has been subject to trade rumors over the last two seasons. The All-Star outfielder’s time in Boston is expected to end in the offseason.
Duran, who hit 20 home runs in 2026 for a second time in his career, could be a good fit for the Philadelphia Phillies, who are looking to address their outfield options this offseason.
#5 Steven Kwan to Milwaukee Brewers
” srcset=”https://www.sme-insights.co.uk/wp-content/uploads/2026/10/7e45c-17933654511465-1920.avif?w=190 190w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/7e45c-17933654511465-1920.avif?w=720 720w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/7e45c-17933654511465-1920.avif?w=640 640w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/7e45c-17933654511465-1920.avif?w=1045 1045w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/7e45c-17933654511465-1920.avif?w=1200 1200w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/7e45c-17933654511465-1920.avif?w=1460 1460w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/7e45c-17933654511465-1920.avif?w=1600 1600w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/7e45c-17933654511465-1920.avif 1920w”>Cleveland Guardians outfielder Steven Kwan is a strong trade candidate in the offseason – Source: Imagn
Cleveland Guardians slugger Steven Kwan is expected to be one of the biggest stars on the offseason trade block. He enters the final year of his contract in 2027.
After winning the World Series, the Milwaukee Brewers will likely look to bolster their squad and could trade for Kwan, a four-time Gold Glove winner, who fits their playing style.
#6 CJ Abrams to New York Yankees
” srcset=”https://www.sme-insights.co.uk/wp-content/uploads/2026/10/9d7b6-17933661832908-1920.avif?w=190 190w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/9d7b6-17933661832908-1920.avif?w=720 720w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/9d7b6-17933661832908-1920.avif?w=640 640w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/9d7b6-17933661832908-1920.avif?w=1045 1045w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/9d7b6-17933661832908-1920.avif?w=1200 1200w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/9d7b6-17933661832908-1920.avif?w=1460 1460w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/9d7b6-17933661832908-1920.avif?w=1600 1600w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/9d7b6-17933661832908-1920.avif 1920w”>Washington Nationals infielder CJ Abrams is expected to be traded in the offseason – Source: Imagn
Washington Nationals shortstop CJ Abrams earned his second All-Star selection in 2026. He had his most productive season at the plate, smashing a career-high 33 home runs with 106 RBIs.
Despite his strong season, the Nationals are expected to trade the All-Star infielder in the offseason. The New York Yankees are one of the strong contenders to trade for Abrams to address their infield issues.
#7 Hunter Goodman to Boston Red Sox
” srcset=”https://www.sme-insights.co.uk/wp-content/uploads/2026/10/9e1d8-17933666847390-1920.avif?w=190 190w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/9e1d8-17933666847390-1920.avif?w=720 720w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/9e1d8-17933666847390-1920.avif?w=640 640w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/9e1d8-17933666847390-1920.avif?w=1045 1045w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/9e1d8-17933666847390-1920.avif?w=1200 1200w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/9e1d8-17933666847390-1920.avif?w=1460 1460w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/9e1d8-17933666847390-1920.avif?w=1600 1600w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/9e1d8-17933666847390-1920.avif 1920w”>Colorado Rockies catcher Hunter Goodman had a career year in 2026 – Source: Imagn
The Boston Red Sox were eliminated in the wild-card series by the New York Yankees for a second consecutive season. The Red Sox’s hitting woes cost them against their AL East rivals.
They could address this by making a blockbuster trade for Colorado Rockies catcher Hunter Goodman, who smashed a career-high 41 home runs this year. The Red Sox could utilize the All-Star slugger as a designated hitter.
#8 Rafael Devers to New York Mets
” srcset=”https://www.sme-insights.co.uk/wp-content/uploads/2026/10/3c6c4-17933671989874-1920.avif?w=190 190w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/3c6c4-17933671989874-1920.avif?w=720 720w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/3c6c4-17933671989874-1920.avif?w=640 640w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/3c6c4-17933671989874-1920.avif?w=1045 1045w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/3c6c4-17933671989874-1920.avif?w=1200 1200w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/3c6c4-17933671989874-1920.avif?w=1460 1460w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/3c6c4-17933671989874-1920.avif?w=1600 1600w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/3c6c4-17933671989874-1920.avif 1920w”>The San Francisco Giants are expected to trade Rafael Devers in the offseason – Source: Imagn
The San Francisco Giants are reportedly looking to trade All-Star infielder Rafael Devers in the offseason to shed his massive contract. The All-Star infielder is owed more than $200 million over the next seven years.
The New York Mets failed to make the postseason for a second straight season in 2026 and could trade for Devers to address their first-base issues. Devers’ power hitting will also take the pressure off star sluggers like Juan Soto.
#9 Drew Rasmussen to Detroit Tigers
” srcset=”https://www.sme-insights.co.uk/wp-content/uploads/2026/10/61618-17933684036012-1920.avif?w=190 190w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/61618-17933684036012-1920.avif?w=720 720w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/61618-17933684036012-1920.avif?w=640 640w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/61618-17933684036012-1920.avif?w=1045 1045w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/61618-17933684036012-1920.avif?w=1200 1200w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/61618-17933684036012-1920.avif?w=1460 1460w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/61618-17933684036012-1920.avif?w=1600 1600w, https://www.sme-insights.co.uk/wp-content/uploads/2026/10/61618-17933684036012-1920.avif 1920w”>Tampa Bay Rays ace Drew Rasmussen could be traded in the offseason – Source: Imagn
Tampa Bay Rays ace Drew Rasmussen, coming off a career year in 2026, has been linked to a trade away from the AL East team this offseason. Rasmussen, who has a $20 million club option for 2027, could be on a new team next year.
The Detroit Tigers, who traded two-time Cy Young winner Tarik Skubal to the Los Angeles Dodgers, could add Rasmussen as a potential replacement.
#10 Tyler Glasnow to Houston Astros
The Houston Astros need to add another high-profile starting pitcher to support All-Star ace Hunter Brown and Los Angeles Dodgers ace Tyler Glasnow fits the bill.
With the Dodgers expected to pursue two-time Cy Young winner Tarik Skubal in free agency, they could trade Glasnow to free up roster space.