Tarik Skubal Blockbuster Trade and Other Bold MLB Winter Meetings Predictions

Tarik Skubal to the Big Apple? Let's get bold.

Skubal, who has won back-to-back American League Cy Young Awards, would command a massive return in a trade. / Steven Bisig-Imagn Images

The movers and shakers are in Orlando, Fla., as MLB's winter meetings began on Monday. Questions and rumors are in the air, and with a star-studded free agent class, as well as some big names potentially available on the trade market, there's the opportunity for some groundbreaking deals to be made.

It wouldn't be unusual territory for the winter meetings, which historically have produced some big moves (Miguel Cabrera to the Tigers, Juan Soto to the Yankees). And we've already seen a couple of big moves, with slugger Kyle Schwarber returning to the Phillies and the back-to-back defending-champion Dodgers landing the best closer available in Edwin Diaz. So, let's get bold and crank up baseball's hot stove with some predictions as the market heats up.

Tarik Skubal is traded to the Mets

Mets receive: SP Tarik Skubal
Tigers receive: SS/OF/2B Jett Williams, SP Jonah Tong, SP Brandon Sproat, RHP Jack Wenninger

Tigers president Scott Harris on Monday said there were “no untouchables” on Detroit's roster, an understandable position given Skubal, the back-to-back Cy Young Award winner, is a free agent in 2026 and could command a deal the Tigers simply can't afford to pay him. The Mets, coming off of a collapse that saw them improbably miss the postseason, are in need of starting pitching, particularly an ace. Landing Skubal, even if it's just for one season, is the kind of move that, coupled with a free agent starter, could transform the Mets rotation overnight into one of the best in MLB. Skubal won't be cheap though. New York would likely have to part with at least three top-10 prospects and another highly touted young arm. In this deal, the Tigers, starving for young pitching prospects in their farm system, land two MLB-ready arms in Tong and Sprout, as well as a promising youngster in Wenninger. Williams, who may not have a clear path to the majors after the Marcus Semien deal, could find an easier lane to the majors in Detroit.

Pete Alonso to the Red Sox

The contract: 4 years, $120 million

Mets fans would very likely be happy with the blockbuster trade above. But they won't be happy with this one. Alonso, a fan favorite who has come up with some clutch hits and made five All-Star teams during his tenure in New York, lands with the Red Sox in a bold swing by the American League East club, adding to an already-fearsome lineup. Boston, after seeing Triston Casas go down to a season-ending injury and infamously—and unsuccessfully—attempting to coax former third baseman and DH Rafael Devers to first base, brings in the slugging Alonso in what could amount to one of the biggest upgrades this winter. Boston first basemen ranked just 21st in Wins Above Replacement in 2025.

Framber Valdez to the Orioles

The contract: 5 years, $140 million

No club had a worse starting pitching situation than the Orioles in 2025. Baltimore starters posted the 26th-worst ERA in the majors, helping to dig an AL East hole the club ultimately could not pull itself out of. The trade of Grayson Rodriguez, arguably Baltimore's best starter when healthy, imported outfield talent but left the rotation starving for an impact arm. Enter Valdez, one of the most durable and reliable starters in the game. He has pitched to a sub-3.50 ERA with at least 190 innings pitched in three of the past four seasons. That's the kind of reliability that would make even the Orioles, who have been reluctant to spend money on free agents in past years, open up their wallets.

Kyle Tucker does not agree to a deal at the winter meetings

Tucker is the best free agent available on the board. While lacking the star power of a Shohei Ohtani or Aaron Judge, Tucker does darn near everything very well, combining a low-strikeout rate with a good eye at the plate while also having the power to hit 30 homers, the wheels to steal 30 bases and the defensive capabilities to win a Gold Glove. Thus far, Tucker has met with the reigning AL champion Blue Jays, who seem to be positioning themselves at the front of the line for the talented outfielder. But there will likely be other suitors, perhaps the Yankees, Dodgers, Giants, Orioles and maybe several surprise clubs as well. Tucker's market seems like one that will take more time to develop, more time than the winter meetings, which end on Wednesday, will allow.

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