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The MLB offseason is officially upon us, and there's more uncertainty, spiked with a shade of existential dread, than we're used to. That's because labor talks are also upon us, with an MLB lockout slated to begin on Dec. 1 barring a minor miracle. There's no clear path to amiable negotiations between the owners and the players at this point, which means next season could be cut dramatically short — or not happen at all, in theory.
With potential changes in cap rules, plus an abbreviated season, plus the ramifications of two small-market teams with dirt cheap payrolls making the World Series, a lot of craziness could unfold this offseason. Let's put a few bold predictions into the world.
Not exactly the boldest of takes given the history of how the Tampa Bay Rays operate. Drew Rasmussen enters his final year under contract with a $20 million club option; that's great value for a Cy Young-caliber ace, but he would immediately become almost threefold Tampa's highest-paid player. The Rays are cheap to their bones, and this season proved that such a strategy can work with the right front office and the right developmental staff.
A potentially shortened season does complicate the return value of a rental, but Rasmussen is one of the 10 or so best pitchers in the game, so Tampa shouldn't find it too difficult to find a taker. He put up a 2.67 ERA and 0.93 WHIP in 30 starts this season; one contender will get very lucky, while Tampa finds yet another creative avenue to replacing a star by committee.
Players with multiple years of club control, such as Jordan Walker, will be extra valuable as teams shy away from overspending on rentals. This seems like an odd time for the St. Louis Cardinals to trade Walker; his name has floated around the rumor mill for years, but St. Louis held tight through the darkest period of his fledging career. Their patience paid off in 2026, as Walker cranked 29 home runs with a .793 OPS. He also won the Home Run Derby.
Typically 24-year-olds fresh off a breakout are viewed as cornerstones, not expendables. Walker is under club control through 2029 and the Cardinals have a real path to contending next season. Then again, Walker was ice cold down the stretch, as the swing-and-miss issues that haunted him once before crept back up.
St. Louis desperately needs pitching. Trading Walker now, at the peak of his value, knowing full well the defensive sacrifices keeping him in right field entails, could be a stroke of genius. If it allows St. Louis to restock on the mound — while replacing him with red-hot prospects like Joshua Báez and Rainiel Rodriguez — it could prove to be yet another instance of Chaim Bloom staying ahead of the curve.
The Philadelphia Phillies need radical changes, both in personnel and approach. There are few more radical changes than Steven Kwan, whose slap-hitting, contact-forward style is diametrically opposed to Philadelphia's offensive stylings in recent years. After another early postseason exit, it's clear the Phillies want to rethink their current setup. This team needs speed, defense and guys who can put together quality at-bats on a regular basis.
After Trea Turner suffered a cataclysmic collapse at the plate in 2026, batting him leadoff is no longer viable. Kyle Schwarber is a sensible leadoff man in the modern era, but his own production plummeted in the final month of the season, and clearly manager Don Mattingly would prefer a more traditional on-base merchant in front of him.
Kwan can provide the Phillies with elite defense in the corner outfield, smart base-running and consistent trips to first base in front of Schwarber, Bryce Harper and the heart of the order. It also allows Turner to slide toward the back half of the lineup, where perhaps he can rediscover his groove with less pressure. Cleveland typically prefers to trade stars, rather than let their contract expire. Kwan is entering a walk year and he's bound to have suitors lined up around the block. Philadelphia, in their desperation, comes through.
With a healthier roster next season, the New York Yankees will need DH reps for Aaron Judge as an act of preservation. Plus Luis García Jr., Ben Rice and perhaps a returning Paul Goldschmidt can all share a slice of the DH pie, depending on the matchup. So what happens with Giancarlo Stanton? He made his long-awaited return as a pinch hitter in October. Given his recent track record of lower leg ailments, it would be unwise for New York to commit to an everyday spot in the lineup. Perhaps even a roster spot is a waste, considering the fact that Stanton cannot run or field.
The veteran slugger is due $15 million next season, in the final guaranteed year of his contract. The Yankees are already expected to float Stanton in trade conversations, but what team is willing to assume the associated risks? Stanton is inflexible in any lineup and it will be difficult to bank on consistent production in his age-37 campaign, even if Stanton can avoid another lengthy stint on the IL.
So, even if it requires eating $15 million in salary, the Yankees will waive Stanton outright to clear a roster spot and move on. He can sign for dirt cheap elsewhere, a simple roll of the dice. `
Several glitzy names are popping up in trade rumors; or more accurately, there's a lot of speculation surrounding the likes of Ronald Acuña Jr., Gunnar Henderson and even Bobby Witt Jr. That said, the most realistic superstar trade candidate this winter is probably Reds shortstop Elly De La Cruz. Cincinnati abides by certain financial restrictions, but more importantly, De La Cruz has already rejected a historic contract extension. Cincy probably would be willing to pay him more than usual, but De La Cruz unabashedly sees a future for himself as a $500 million-plus free agent — and probably playing in a more competitive market.
Should the Reds cash in now, it's a chance to revamp their farm system and lay a more complete foundation. De La Cruz is a mega talent and the Reds should not trade him lightly, but for a proper godfather offer, really anyone in baseball can be available. Cincy is coming off of a disappointing campaign and probably doesn't feel great about its current direction. De La Cruz has three more years of arbitration left, one of which could be a short season. That time will pass quickly.
Enter the Los Angeles Dodgers, who are down in the dumps after finally meeting their match in the NLCS. Los Angeles could use an upgrade in the infield and the Dodgers are also equipped with the best farm system in baseball. We've typically seen the Dodgers hunt marquee free agents and focus on development at the farm level, but trading for De La Cruz — not unlike the Mookie Betts trade once upon a time — could vault L.A. back to the mountaintop.
I know, I know. The Detroit Tigers had a shot to extend Tarik Skubal — kind of. Skubal is a Scott Boras client and he was never going to sign an extension. Still, Detroit's unserious offers became a huge sticking point in the media, and all but insured his departure at the trade deadline. After a half-season in L.A. and a postseason run that came up short, however, Skubal is officially on the market. Might the Tigers circle back?
Skubal has made it clear on several occasions that he loves Detroit and would love to finish his career in a Tigers uniform. If Detroit put the best offer on the table, or even a comparable offer to L.A. or another big-market contender, I'm not sure Skubal would need to think twice.
The Tigers handed Framber Valdez a $37.5 million annual contract last winter, granted on a short-term deal. So the team can spend in free agency, and perhaps there is more motivation now as this talented young core levels up. Detroit and Skubal share a bond deeper than baseball. I'd bet Detroit at least puts its hat in the ring and is worth talking about in the Skubal sweepstakes, even if the Tigers' bid ultimately falls short. (It almost certainly will.)
This will be an outside-the-box free agency, so why not dial up an outside-the-box landing spot for Skubal. The talented southpaw has two "obvious" landing spots: the incumbent Dodgers or the New York Mets, the two richest teams in baseball. But what about the Toronto Blue Jays, who time and time again seem to pop up in high-profile free agency conversations? Toronto came in second for Shohei Ohtani and Juan Soto and Kyle Tucker. The same Blue Jays dropped $210 million on Dylan Cease in December and inked Vladimir Guerrero Jr. to a $500 million extension.
The Blue Jays have money to burn. Moreover, coming off of a disappointing follow-up to their 2025 pennant run, there's more pressure than ever for Toronto to do something. Anything! With money coming off the books, there's not much (besides an improbable salary cap) to prevent Toronto from going all-in for Skubal. Kevin Gausman is no longer around; Max Scherzer is bound for retirement and the Shane Bieber experiment spoiled. A four-headed monster of Skubal, Cease, José Soriano and Trey Yesavage sure sounds nice.