While a majority of the focus for baseball fans during the winter centers on MLB free agency, blockbuster trades can be just as crucial to a team’s success. Last winter, the biggest MLB trades saw the Chicago Cubs land Kyle Tucker and the Boston Red Sox acquired Garrett Crochet. We expect more mega deals this offseason.
Let’s dive into five MLB trades we’d love to see this winter.
San Francisco Bolster Rotation with Sonny Gray Trade
The San Francisco Giants obviously need starting pitching, coming off a season where the rotation ranked 17th in ERA (4.10) despite having one of the most pitcher-friendly parks in baseball. MLB free agency is an option, but the bidding war for Dylan Cease could get out of San Francisco’s price range, and Framber Valdez might not be a great clubhouse fit given he seemed to intentionally hit a catcher with a pitch this past season. So, the trade market becomes the next option.
- San Francisco Giants trade: RHP Keyner Martinez, LHP Joe Whitman
A trade with the rebuilding St. Louis Cardinals, who are willing to eat some of the remaining money on the Sonny Gray contract, seems perfect. St. Louis can eat $10 million of Gray’s remaining contract, which effectively lowers his salary to $25 million added to the Giants payroll. It’s cheaper than a front-line starter cost to sign on the open market. Gray returns to the Bay Area, where his major-league career began, while the Cardinals free up $25 million in payroll and pick up two of the Giants’ top pitching prospects.
Related: Top Offseason MLB Trade Candidates, Potential Landing Spots
San Diego Padres Address Catcher with Ryan Jeffers Trade
In 2024, San Diego Padres catchers finished 25th in OPS (.614) and 27th in fWAR (0.4) at the position. It’s obviously an area of need for San Diego, but there aren’t any great options in free agency and an in-season trade for a catcher is rare for a reason. However, the Padres could make a calling to the rebuilding Minnesota Twins this winter.
- Minnesota Twins trade: Ryan Jeffers
- San Diego Padres trade: LHP Jagger Haynes
In this proposed deal, Minnesota picks up San Diego’s No. 10 prospect in Jagger Haynes as the primary prospect. The 6-foot-3 southpaw reached Double-A ball last season, recording 101 strikeouts in 103 innings pitched. While his command needs work, he could work his way into the Twins rotation by September. Meanwhile, San Diego picks up Jeffers for the 2026 season, with the right-handed hitter offering a strong bat (.772 OPS since 2023).
Related: MLB Free Agency Predictions 2025
Tampa Bay Rays Trade Brandon Lowe to the Kansas City Royals
It’s a tradition as old as time, the Tampa Bay Rays dumping salary over the winter to lower payroll, and they pick up prospects who they turn into key contributors. This winter, it seems like a matter of when and not if All-Star second baseman Brandon Lowe is traded. Tampa Bay has already exercised Lowe’s $11.5 million club option for next season, so the next step could be a deal with the Kansas City Royals.
- Tampa Bay Rays trade: Brandon Lowe
- Kansas City Royals trade: RHP Luinder Avila, LHP Franz Mozzicato
Lowe, who put up a .780-plus OPS for the second consecutive season in 2025, would be an instant upgrade for a Royals lineup that received a collective .640 OPS from its second basemen last season. The veteran also offers the ability to play first base when necessary. In exchange, Tampa Bay gets righty Luinder Avila after the 24-year-old put up a 1.29 ERA in his cup of coffee with Kansas City (14 innings) for bullpen depth, and the organization gets to take on former first-round pick Franz Mozzicato (7th overall pick in 2021 MLB Draft) as a potential reclamation project.
Milwaukee Brewers, New York Mets Swing a Freddy Peralta Trade
Trades are often about relationships and history. New York Mets president of baseball operations David Stearns certainly has that with the Milwaukee Brewers, the team who he served as the general manager for from 2015-2023. He also knows the front office has a tendency to move top players in contract years and that’s the boat starter Freddy Peralta finds himself in.
- Milwaukee Brewers trade: Freddy Peralta
- New York Mets trade: RHP Brandon Sproat, OF/2B A.J. Ewing, Eli Serrano III
Peralta, who earned his second All-Star selection in 2025, recorded a league-high 17 wins this past season with 204 strikeouts and a 1.07 WHIP across 176.2 innings pitched. He’s only under contract for one more season, but he’s exactly the caliber of front-line starter the Mets rotation needs. In exchange, New York parts ways with its No. 5 prospect Jonah Tong, who could quickly become a long-term future in the Brewers rotation. Milwaukee also adds New York’s No. 2 prospect, the versatile A.J. Ewing, who could play center, left field, and second. Outfield prospect Eli Serrano III, coming off a season in High-A with a .690 OPS, would be the sweetener.
Read More: Most Overrated MLB Free Agents 2025-26
Los Angeles Dodgers Help Out Bullpen Depth with JoJo Romero
The Dodgers’ bullpen needs to be addressed this winter. A high-priced addition in free agency is certainly on the table, but a smaller trade also shouldn’t be ruled out. In steps St. Louis, a franchise Los Angeles has plenty of history trading with in recent years.
- St. Louis Cardinals trade: JoJo Romero
- Los Angeles Dodgers trade: OF Kendall George
Left-handed reliever JoJo Romero, a California native, joins the back-to-back World Series champions in a contract year. Walks (11.4 percent walk rate) were a bit of an issue for him last season, but he held opponents to a .210 batting average allowed and registered a 2.07 ERA in 61 innings of work. The Dodgers pick up a reliable left-handed reliever to strengthen their bullpen, and the Cardinals get to take a chance on the athleticism of outfielder prospect Kendall George, a first-round pick in the 2023 MLB Draft.
