6 Realistic MLB Trades That Could Happen In 2026-27 Offseason

While eight of Major League Baseball's 30 fanbases remain extremely invested in finding out who will win the 2026 World Series, nearly three-quarters of the league has already shifted into offseason mode.

And what a weird offseason it is going to be.

Whether we end up losing any or all of the 2027 season remains to be seen, but there's seemingly a 99.9 percent chance there will be a lockout when the current collective bargaining agreement expires at 11:59 p.m. ET on Dec. 1 without a new agreement in place—at which point teams can neither sign players to MLB contracts nor conduct any trades until the lockout ends.

That doesn't mean there won't be trades all offseason, though. Let's not forget the last time there was a lockout (2021-22), the A's traded away Matt Chapman, Matt Olson and Chris Bassitt within the first week back in business.

So, while the "when" part is quite up in the air, here are several swaps that could make sense for this offseason for all parties involved.

Yankees Leverage Pitching Surplus

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Ryan Weathers

New York Yankees send:

RHP Luis Gil (arbitration eligible through 2028)

LHP Ryan Weathers (arbitration eligible through 2028)

Chicago White Sox send:

SS/3B/CF Caleb Bonemer (Double-A Prospect; No. 27 overall on MLB pipeline)

RHP Pierce George (Triple-A Prospect)

Max Fried is signed through 2032. Cam Schlittler won't hit free agency for the first time until after the 2031 campaign. And both Gerrit Cole and Carlos Rodón are signed through 2028.

The Yankees also have four more years of Will Warren, two years left on both Luis Gil and Ryan Weathers, one more season of Clarke Schmidt and two MLB-ready 23-year-olds in Elmer Rodríguez and Carlos Lagrange.

That's quite the stockpile of starting pitching that they could use to perhaps pluck a quality prospect from a team that needs to bolster its rotation.

Speaking of positional surpluses, the Chicago White Sox have three players rated as top 100 prospects, per MLB.com's pipeline. All three are shortstops, including 2026 No. 1 overall draft pick, Roch Cholowsky.

But in Colson Montgomery and Chase Meidroth, the White Sox already have a middle infield tandem that is arguably top five in the majors in terms of defensive proficiency, plus Miguel Vargas fresh off an All-Star season at third base—and all three of those guys are under team control through at least 2029.

Recognizing this logjam (and his less-than-stellar glovework), they started giving Caleb Bonemer some reps in center field late in the 2026 season, giving him more paths to playing time in the majors after he clubbed 37 home runs in the minors this season.

Using him as a trade chip could also work, though, if the return is not one, but two starters who could be middle-of-the-rotation arms for them for the next two years.

Steven Kwan Finally Gets Traded

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Cleveland Guardians send:
OF Steven Kwan (arbitration eligible in 2027)

Chicago Cubs send:
RHP Jaxon Wiggins (Triple-A prospect)
UTIL James Triantos (controllable through at least 2032)

Steven Kwan made $7.725M in arbitration for 2026. His 2027 salary is very likely to climb north of $10M.

And, well, unless it's for José Ramírez, the Guardians don't like dedicating eight figures to an individual player's salary.

At any rate, two winters ago, they traded away the final five seasons of their seven-year contract with Andrés Giménez, and subsequently shipped Josh Naylor to Arizona, rather than paying what ended up being a $10.9M salary in his final year of arbitration eligibility.

Despite their penny-pinching ways, they just keep making the postseason, winning the AL Central for the seventh time in 11 years.

So, if they can turn one year of Kwan into a pair of former second-round picks, history suggests they probably will.

On the Cubs' side of this one, they are losing a boatload this winter, including four of the six players who appeared in at least 20 games in the outfield in 2026. Pete Crow-Armstrong in center is a fantastic starting point, but Matt Shaw in right and either Justin Dean or Kevin Alcantara in left figures to be the plan as currently constructed.

"Losing a boatload" does also mean "has money to spend." But trading for one year of Kwan at $10M-$12M would allow them to do their real spending on the pitching staff, where they need it most.

Though Kwan is nowhere near the home run threat that Happ is, his career .739 OPS isn't drastically different from Happ's mark of .772 over the past five seasons. Both left fielders also won Gold Gloves in each of the past four years, so it could be quite the seamless transition.

On the prospects front, Jaxon Wiggins entered 2026 as a top 100 prospect on Baseball America, Baseball Prospectus and MLB, but he was a mess at Triple-A Iowa, walking nearly 20 percent of batters faced. Maybe Cleveland can fix his command, though, while James Triantos has .300 batting average / 30 stolen bases potential to replace Kwan.

Logan Gilbert to the Highest Bidder?

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Seattle Mariners send:
RHP Logan Gilbert (arbitration eligible in 2027)

Minnesota Twins send:
OF Emmanuel Rodriguez (controllable through at least 2032)
RHP Riley Quick (Double-A prospect)
IF Ben Ross (controllable through at least 2032)

First things first, the Mariners aren't throwing in the towel.

The 2026 season was a major disappointment, but they are still very much in their "win now" window. They just kind of have to hope/assume that Julio Rodríguez, Cal Raleigh and Josh Naylor bounce back from what was a combined OPS of roughly .680.

But between Emerson Hancock's breakout, Kade Anderson's arrival and Logan Gilbert's projected salary of $16M in his final year of arbitration eligibility, the M's might consider trading away the ace who was their Opening Day starter in both 2025 and 2026.

At any rate, this starting rotation would still be quite formidable even without Gilbert. In addition to Hancock and Anderson, Seattle has George Kirby (through 2028), Bryan Woo (through 2029) and Bryce Miller (through 2029) for another two years. Ryan Sloan is also one of the top pitching prospects in all of baseball, and he might be a factor by the end of 2027.

They aren't just going to salary dump Gilbert, though.

Seattle ought to be able to fetch a return on par with what the Brewers got for one year of Corbin Burnes and one year of Freddy Peralta in recent years—namely, an MLB-ready pitching prospect and a position player prospect who both rank around 100th overall.

So, who is arguably one quality pitcher away from becoming a contender in 2027 and has the means to put together that type of package?

Maybe Detroit.

Possibly Baltimore or Miami.

St. Louis isn't out of the question.

But Minnesota might be most desperate of all, with Joe Ryan, Dean Kremer, Pablo López, Bailey Ober, Jeff Hoffman and Trevor Larnach each one year away from free agency and Byron Buxton not getting any younger.

The Twins wouldn't want to part with either Walker Jenkins or Kaelen Culpepper, but three guys a bit lower on their prospects list could be doable—with Emmanuel Rodriguez immediately becoming a candidate to fill the Randy Arozarena-sized hole in Seattle's outfield.

Buy Low on Spencer Strider?

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Atlanta Braves send:

RHP Spencer Strider ($22M in 2027, $22M in 2028, $22M club option (or $5M buyout) for 2029

Cash Considerations

Baltimore Orioles send:

OF Nate George (High-A prospect)

SS Wehiwa Aloy (Double-A prospect)

Outside of the rampant speculation of a possible Mason Miller blockbuster, the biggest non-trade of this year's deadline was the rumor that Spencer Strider might have gone to the Texas Rangers if Jacob deGrom hadn't invoked his no-trade clause to block it from happening.

When he was healthy, Strider was all sorts of special, arguably the best pitcher in all of baseball between the 2022 and 2023 campaigns. There were also flashes of his former dominance during the 2025 season, making 11 quality starts. But he missed almost all of 2024 and most of 2026 to injuries and might never get back to what he used to be.

Could the Braves revisit that attempt to get out from under the remainder of this contract?

And is anyone willing to help them do so?

Baltimore could be a great fit, especially if Atlanta is willing to retain some of the (at least) $49M still due to Strider.

At the moment, the Orioles' starting rotation for 2027 looks like Shane Baz, Kyle Bradish, Brandon Young and some serious question marks. And with Chris Bassitt, Zach Eflin, Andrew Kittredge and more coming off the books, they should have room in the budget to take a gamble on Strider.

At any rate, they're going to have to invest in pitching, unless they're irrationally confident in two of Cade Povich, Trey Gibson and Luis De León making an impact in 2027. Why not Strider if they can get him?

Milwaukee Brewers Do It Again

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Trevor Megill

Milwaukee Brewers send:

RHP Trevor Megill (arbitration eligible in 2027)

Pittsburgh Pirates send:

C Easton Carmichael (Double-A prospect)

OF Lonnie White Jr. (Double-A prospect)

It's not officially the offseason until the Brewers trade away their final year of team control on a star player.

Traditionally, said player on the move is a pitcher.

Last winter, they sent Freddy Peralta to the Mets for a pair of prospects. The previous year, it was Devin Williams to the Yankees for Nestor Cortes and Caleb Durbin. The year before that, they traded Corbin Burnes to the Orioles for DL Hall and Joey Ortiz. And while they didn't do anything too big during the 2022-23 offseason, that's because they had already sent the Padres 1.5 years' worth of Josh Hader for four players at the 2022 trade deadline.

So, while they also have William Contreras prominently on their list of players who will hit free agency next winter, the Brewers trading away their final season of closer Trevor Megill might as well be the free space on the Bingo board of offseason trade predictions.

The 'where' part of the deal is much less of a freebie.

But do you know who really needs to address the back of its bullpen and is really sick and tired of facing Megill?

That would be the Pittsburgh Pirates, against whom Megill has made 18 appearances with a 0.51 ERA and 0.62 WHIP.

Pittsburgh finally had a winning season in 2026, but fell a few games shy of the much bigger goal of making it back to the postseason. Maybe Megill is the missing piece that gets them there.

And if Megill does get dealt, get ready for Abner Uribe to become the next All-Star closer in Milwaukee. They've got him under team control through 2030, and he has a 2.20 ERA through his first 182 big league appearances.

Hunter Goodman Relocates to a Contender

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Colorado Rockies send:
C Hunter Goodman (arbitration eligible through 2029)

Texas Rangers send:
RHP Caden Scarborough (High-A prospect)
RHP AJ Russell (High-A prospect)
C Malcolm Moore (Double-A prospect)

Lost amid the embarrassment of the Rockies enduring yet another season of more than 100 losses, Hunter Goodman did quite a bit of mashing with 41 home runs in his 574 trips to the plate. That translates to a home run in 7.1 percent of his plate appearances, which was the highest ratio in the majors this season.

Before you even think about trying to chalk that up to Coors Field being Coors Field, note that for the second consecutive year, Goodman hit roughly 60 percent of his home runs on the road.

His power plays everywhere, and it's about time it gets to play for a contender.

Granted, Colorado's track record when it comes to trading away star players hasn't been great, to say the least. The Rockies didn't get much other than salary relief when they shipped out Ryan McMahon two summers ago. They never did manage to sell off Trevor Story before he hit free agency. And that Nolan Arenado trade back in February 2021 was an all-timer of a disaster.

But if they put him on the trade block and just wait for the offers to pour in, they should be able to get quite the haul for three years of Goodman's services.

For Texas, the catcher spot in the lineup was a season-long struggle and they have both Elias Díaz and Kyle Higashioka hitting free agency. They're also slated to lose primary DH Joc Pederson, so a slugging C/DH would be a huge pickup for them.

They're also pretty firmly in a "now or never" spot with their roster construction—Jacob deGrom turns 39 in June; Nathan Eovaldi turns 37 in February and has just one year left on his contract—and might be desperate enough to part with several of their top prospects.