In reporting on potential talks for a long-term deal between the Tigers and Skubal, Heyman noted there is an “immense gap.”

“It turns out the Tigers’ offer a year ago to Skubal was below $80 million for four years,” Heyman writes. “It was only reported here originally to be less than the $170M the Red Sox signed Garrett Crochet for, and it’s actually less than half. Evan Petzold of the Detroit Free Press later reported it was under $100M.”

Tigers pitcher Tarik Skubal celebrates striking out Mariners catcher Cal Raleigh in the sixth inning of ALDS Game 5 at T-Mobile Park in Seattle on Friday, Oct. 10, 2025. / Junfu Han / USA TODAY NETWORK via Imagn Images

The Case For Making A Trade

Those contract talks matter because Skubal is scheduled to be a free agent following the 2026 season. If the Tigers don’t feel like they can sign their ace to a long-term deal, they might have no choice but to trade Skubal rather than letting him walk away in free agency without getting anything in return.

The Yankees certainly know how to spend money, so signing Skubal to a long-term contract shouldn’t pose an issue. They’ve already given massive deals to Gerrit Cole (nine years, $325 million), Carlos Rodon (six years, $162 million) and Max Fried (eight years, $218 million).

Adding Skubal to that mix would give the Yankees a “super rotation” unlike anything we’ve seen in decades. The last time we saw a club with four 20-game winners in the rotation was the 1971 Baltimore Orioles: Jim Palmer, Dave McNally, Mike Cuellar and Pat Dobson.

Skubal could be the ace of aces in the Bronx. The 28-year-old is expected to win his second straight American League Cy Young Award this year after leading the league with a 2.21 ERA. His 7.6 WAR and 0.89 WHIP also topped the AL. He finished second to Crochet in strikeouts, recording a career-best 241 whiffs.

Signing Skubal would also keep the World Series window open for right fielder Aaron Judge, who’s not getting any younger.

The Case Against Making A Trade

To get something, you have to give up something. NJ.com’s Randy Miller and Bob Klapisch pitched a deal involving pitchers Clarke Schmidt and Luis Gil, along with prospects Jasson Dominguez and/or Spencer Jones. That’s a lot of young talent that would be going out the door for one arm.

While it is an elite arm, it would also mean that three of the Yankees’ top four starters are left-handed. Is that a problem for manager Aaron Boone?

Oct 10, 2025; Seattle, Washington, USA; Detroit Tigers starting pitcher Tarik Skubal (29) reacts after striking out Seattle Mariners catcher Cal Raleigh (not pictured) during the sixth inning during game five of the ALDS round for the 2025 MLB playoffs at T-Mobile Park. Mandatory Credit: Steven Bisig-Imagn Images / Steven Bisig-Imagn Images

There’s also the money factor. How much of it is Hal Steinbrenner willing to spend to deliver a World Series title to the Bronx for the first time since 2009?

The Yankees already have massive, nine-figure deals on the books for Judge (nine years, $360 million), Giancarlo Stanton (13 years, $325 million), Cole, Rodon and Fried.

In addition the Yankees face the prospect of re-signing outfielder Cody Bellinger to a huge contract or forking over Monopoly money for Chicago Cubs outfielder Kyle Tucker, the best position player on the open market.

And what if the Yankees can’t sign Skubal to a long-term deal and still trade for him? It could be Juan Soto all over again with a one-and-done in pinstripes.

Prediction

Given how much Skubal would cost in terms of dollars and prospects, a deal by the Yankees seems unlikely.

But we all know that you can never say never when it comes to general manager Brian Cashman wheeling and dealing.