The perfect $100 million contract Yankees must offer Dylan Cease to steal him from Padres

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The perfect $100 million contract Yankees must offer Dylan Cease to steal him from Padres

Russell Steinberg, ClutchPoints · ClutchPoints

Tue, Oct 21, 2025 ·

4 min read

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The post The perfect $100 million contract Yankees must offer Dylan Cease to steal him from Padres appeared first on ClutchPoints .

Starting pitching will not be the New York Yankees ' top priority this offseason — nor should it be. The Yankees' American League pennant defense fell short in the ALDS as Max Fried and Carlos Rodon turned in subpar performances at the worst possible time, but both are still All-Stars, and Fried will get his share of real estate on Cy Young ballots.

They're also getting Gerrit Cole back in 2026 and can add him into a rotation that also includes — in addition to Fried and Rodon — breakout star Cam Schlittler , 2024 Rookie of the Year Luis Gil and, eventually, a post-Tommy John Clarke Schmidt .

The Yankees will instead focus on their frighteningly inconsistent bullpen and their lineup around captain Aaron Judge .

So why should New York go after Dylan Cease ?

First of all, there's the obvious. They say you can never have too much starting pitching, and the Yankees know that better than anyone. Cole, Rodon and Schmidt are all expected to start next season on the injured list , and that's still with the possibility out there that something happens in spring training to another starter.

The Yankees will need more arms and it's likely one or more pitchers will go down along the way as the team navigates a 162-game season. The notion that there's no room for Cease just doesn't make sense in modern baseball.

But that alone doesn't mean the Yankees should open their wallets and spend nine figures on a starter just for funsies. Cease specifically should be a tantalizing option for an organization that wants to toe the line between being payroll-conscious and aggressive in free agency.

Dylan Cease hits free agency at an awkward time

While Cease might not be the best all-around starting pitcher on the market in 2025, there's an argument that he could provide the most bang for a club's buck — and that's the quality the modern Yankees covet.

The upside that Cease brings is as good as anybody's. He has twice finished in the top-five in Cy Young voting and twice led the league in strikeouts per nine innings, and that's from four separate years. He has also been one of the most dependable pitchers in baseball , starting at least 30 games in all five of his complete MLB seasons.

The best season of his career came in the American League, as well. In 2022, he had a 2.20 ERA in 32 starts, striking out 227 batters in 184 innings pitched with the Chicago White Sox .

That should all add up to a massive contract, and make no mistake: Cease is going to get paid handsomely. But he's also coming off of arguably the worst season of his career and is entering his age 30 season. His ERA+ (94) put him slightly below league average, but his FIP (3.56) shows luck may account for part of that.

These are all variables his suitors will need to take into account.

Dylan Cease' potential contract value with the Yankees

Spotrac projects Cease to be worth just north of $26.4 million per year and projects a six-year, $158.5 million contract in free agency. It's unlikely the Yankees would want to commit that many years to Cease considering Cole, Fried and Rodon are all under contract into their late 30s.

That might not be a problem. We've seen a trend in recent years of players waiting out free agency, not getting what they want and signing a one-year deal somewhere as an audition for something bigger the next offseason. The Yankees don't need to only offer Cease one year, but they can give him an opt-out after the first year if he has a strong season.

A qualifying offer in 2025 is worth $22.02 million and the Padres will almost certainly extend one to Cease, who will almost certainly decline.

Using that as a baseline, if Cease is still available with no team willing to offer him something long-term, it would make sense for New York to swoop in.

The should offer him a four-year contract worth $100 million ($25 million AAV)with an opt-out after year one.

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