Brian Cashman speaking

On November 4, the New York Yankees agreed to keep Gerrit Cole around for another four seasons, a wise decision from both sides. Cole will now stay in the Bronx and the Yankees will get their ace back.

While having Cole back in the rotation was the first step in making this rotation elite in 2025, the Yankees will have other needs in that department. Fortunately for them, there are multiple starters on the market, including right-hander Jack Flaherty.

Flaherty revived his career in 2024, giving the Los Angeles Dodgers help down the stretch and in the playoffs. He might’ve raised his stock more than any pitcher on the market, as he could be looking at a $100 million deal.

Darragh McDonald of MLB Trade Rumors was the latest to suggest he would. In his prediction, McDonald wrote that Flaherty would sign a five-year, $115 million deal with the Yankees in MLB free agency.

“As far as “prove-it” deals go, Flaherty stands as one of the most successful cases in recent memory. The former first-round pick and top prospect went from one of the National League’s burgeoning young aces to an injury reclamation in a span of just a few years, as shoulder injuries derailed his momentum after a brilliant 2019 campaign…

“Flaherty posted a 2.95 ERA, 32% strikeout rate and 4.6% walk rate in 18 brilliant starts with Detroit. He wasn’t quite as good with Los Angeles, but he still gave the Dodgers 55 1/3 innings of 3.58 ERA ball, fanning 26.1% of his opponents against an 8.1% walk rate,” McDonald wrote on November 4. “The season-long numbers remained strong overall, and Flaherty will now return to the open market ahead of his age-29 season — making him the youngest of the top end starters available — and without a qualifying offer, as he’s ineligible to receive one after being traded midseason.”

Yankees Had Interest in Flaherty During the Trade Deadline

The New York Yankees showing interest in Flaherty this winter wouldn’t come as much of a surprise.

It was reported before the trade deadline that they were interested in landing him, but he was eventually dealt to the Los Angeles Dodgers.

According to Jon Heyman of the New York Post, the Yankees were worried about a lower back injury Flaherty was believed to be suffering.

“The Yankees were down the road on a potential deal they’d been discussing with the Tigers for Flaherty before backing away over a perceived lower back situation,” Heyman wrote on October 24. “That opposing call didn’t hurt the Yankees too much, since they weren’t rotation poor and wound up as the only playoff team with extra starters. Coveted right-hander Will Warren was one the Tigers apparently sought.”

Despite those talks since the trade deadline, Yankees general manager Brian Cashman told reporters they simply couldn’t get a deal done for him.

“At the end of the day, I would’ve brought Jack Flaherty in if I could’ve matched up, and I had difficulty matching up,” Cashman said, according to Jorge Castillo of ESPN. “And that was the reason I don’t have him.”

How Flaherty Would Help the Yankees

The New York Yankees rotation saw in the postseason why it could be better. Pitching wins games in big moments, and if they had Flaherty, perhaps things would’ve been different.

While the right-hander has some concerns after struggling prior to this campaign after posting a 4.84 ERA between 2022 and 2023, his showing this year was one to remember.

With 194 strikeouts in 162.0 innings pitched, there’s reason to believe Flaherty is back to what he once was. His strikeout stuff was elite, and it was a promising sign for a team like the Yankees, who might want to sign him to a long-term deal.

Jon Conahan covers the NBA and NFL for Heavy.com. Since 2019, his sports coverage has appeared at Sports Illustrated, oddschecker, ClutchPoints and Sportskeeda. More about Jon Conahan