🔥 BLOCKBUSTER TRADE INCOMING: Top MLB insiders predict the Boston Red Sox are preparing to make a massive move for an $18 million Cy Young–winning lefty — a bold attempt to rebuild their rotation, reignite Fenway’s fire, and send a clear message that Boston is ready to rise back into contention.

Red Sox Tabbed to Trade For $18 Million Cy Young Lefty by Top MLB Insider

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Manager Alex Cora of the Boston Red Sox.

The Baseball Writers’ Association of America announced its finalists for the American League Cy Young Award earlier this week. One is last year’s Cy Young winner, Tarik Skubal of the Detroit Tigers. He is joined by another dominant lefty who had his breakout season in 2025, and whose numbers were close to identical with Skubal’s — Garrett Crochet of the Boston Red Sox.

The third nominee, righty Hunter Brown of the Houston Astros, also has an outstanding season with a 2.43 ERA and 266 strikeouts over 185 1/3 innings. But Skubal and Crochet are clearly the co-favorites for the award that will be announced November 12.

But what if the two co-favorites ended up on the same team in 2026? According to ESPN’s longtime baseball insider Buster Olney, that eye-popping and seemingly far-fetched scenario is a real possibility. Olney on Wednesday wrote that the Tigers could actually trade Skubal this offseason — and the Red Sox are “well positioned” to land him.

“Other teams believe the Tigers will seriously consider moving him if they can glean what they want in a trade — and there is every reason to expect a significant bidding war for Skubal, who will be eligible for free agency after next season,” Olney wrote. “The Red Sox are well-positioned to make a run at Skubal, if they want.”

Tigers Could be Forced to Deal Skubal

Olney continued, saying that “the only sure thing in this situation, it seems, is that Skubal will not sign a long-term deal with Detroit before he reaches free agency, and that will frame the Tigers’ decision-making.”

If Olney is correct about Skubal’s intentions, the Tigers could be backed into a corner, essentially forced to trade Skubal or risk losing the lifetime 3.08 ERA southpaw for nothing in return, beyond a compensatory draft pick.

But by trading Skubal, the Tigers who already have baseball’s No. 2 and No. 8 overall prospects in shortstop Kevin McGonigle and outfield speedster Max Clark, could fortify a formidable farm system — already ranked fifth in the league in Bleacher Report‘s end-of-season ratings — with a serious upgrade.

Few teams are in better position to accommodate Detroit than the Red Sox.

To obtain Crochet in a trade with the Chicago White Sox last offseason, Red Sox chief baseball officer Craig Breslow gave up four of the organization’s most prized prospects, including catcher Kyle Teel — the team’s fourth-ranked prospect at the time — and Braden Montgomery who just a few months earlier Breslow had made the Red Sox’ first-round draft pick.

2025 1st-Round Pick Heads Possible Package

Assuming that it would take the same prospect haul to trade for Skubal — three top 20 organizational prospects plus the team’s first-round pick from the same year — who would the Red Sox need to surrender to bring Skubal aboard and create the indisputably most intimidating one-two starting rotation punch in the Major Leagues?

The Red Sox first-round pick this year, 15th overall (Montgomery was picked 12th), was Kyson Witherspoon, a 21-year-old righty out of Oklahoma with a fastball that peaks at 99 mph.

Witherspoon is already rated fourth in the Red Sox system by MLB Pipeline, so it may take another top-five prospect in the package as well. A likely candidate would be No. 3 prospect, power-hitting outfielder Jhostynxon
Garcia.

Pitcher and ‘5 Tool’ Outfielder Round Out Potential Trade

Pitcher Wikelman Gonzalez, at the time No. 8 in the Boston system, was also included in the Crochet trade. An equivalent prospect could be the current No. 10, 24-year-old righty David Sandlin, another Sooners product who was acquired by the Red Sox in a 2024 trade for setup man John Schreiber.

Finally, moving down the Red Sox top 20, No. 15 prospect Miguel Bleis, a “five tool” outfielder out of the Dominican Republic, per MLB Pipeline, who was signed in 2021 for a $1.5 million bonus — the priciest international amateur free agent in the Red Sox class that year — appears a likely candidate to round out the package that could nab Skubal and elevate the Red Sox to become an early favorite to reach the World Series in 2026.

Jonathan Vankin JONATHAN VANKIN is an award-winning journalist and writer who now covers baseball and other sports for Heavy.com. He twice won New England Press Association awards for sports feature writing. He was a sports editor and writer at The Daily Yomiuri in Tokyo, Japan, covering Japan Pro Baseball, boxing, sumo and other sports. More about Jonathan Vankin