Garrit Cole on the mound pitching

The seemingly perpetual New York Yankees starting pitching conversation is back.

Going into 2025, the Yankees had to feel good about their Gerrit Cole-Max Fried-Carlos Rodón-Clarke Schmidt-Luis Gil rotation, with Marcus Stroman as either a sixth starter or long reliever.

However, with Gil out until at least midseason, Cole lost until 2026, and Stroman’s status up in the air, New York already finds itself in a hole that feels all too familiar.

A Familiar Face Returning to New York?

One option could be a reunion with St. Louis Cardinals starter Sonny Gray, who spent a year-and-a-half in the Bronx from 2017-18 and has three years left on his $75 million deal.

Here is what Peter Chawaga of Newsweek had to say on Cole and Gray:

“When Cole broke his silence with the media after undergoing his surgery, MLB .com’s Bryan Hoch provided an update that the pitcher is targeting a 14-month recovery period , which would put him back on the mound in July 2026, assuming the 34-year-old doesn’t experience any setbacks. NJ.com ‘s Bob Klapisch pointed out that he might return  with less velocity than ever, given the mileage on his arm.

In an early New York Yankees trade deadline prediction, Jomboy Media’s Joez McFly singled out Sonny Gray of the St. Louis Cardinals , who could help the Yankees bridge the gap without Cole this year and into the near future.

‘The Yankees will trade for Sonny Gray,’ McFly predicted.

After signing a three-year, $75 million contract in 2023, Gray is owed $25 million this season, $35 million in 2026 and has a $30 million club option for 2027. If the Yankees feel he’s worth the money and whatever assets they need to give up to get him, he could be the perfect fit for their timeline.”

Will New York Want to Experiment With Sonny Gray Again?

Gray was a frustrating experiment for New York Yankees fans the last time around, with some of his worst career years coming in pinstripes.

In 2017, Gray went 4-7 with a 3.72 ERA and a 4.87 FIP over 65 and 1/3 innings. He produced a similar line over two postseason starts. It was an okay campaign for Gray, particularly considering none of his return pieces (prospects Dustin Fowler, James Kaprielian, Jorge Mateo) ever properly materialized for the Oakland Athletics.

In 2018, Gray’s first and final full season with New York, he went 11-9 with a 4.90 ERA and a 4.17 FIP over 130 and 1/3 innings. Again, an underwhelming performance that left fans wanting more from a pitcher who has now finished in the top seven of Cy Young voting three times.

The reunion McFly alluded to is a nice idea on paper, as adding a proven veteran with experience as a Yankee makes sense for this depleted staff. This is a team that flirted with a World Series last October, and still has plenty of cornerstone pieces for a win-now mentality.

Even without Cole, this staff can dominate at full health, backed by a bullpen with a 3.33 ERA—seventh-best in the majors.

However, sour memories and a pricey tag would be unlikely to elicit faith from the fanbase. Gray can help this team, but this does not feel like a match made in heaven.