Sonny Gray New York Yankees
(Photo by Elsa/Getty Images)


The New York Yankees’ Sonny Gray debacle could soon be over, as long as the Bombers don’t get too greedy.

Aaron Case

Get your picklebacks ready to toast the departure of Sonny Gray. The MLB Winter Meetings started on Sunday, and the New York Yankees are drawing trade interest for Pickles from the San Diego Padres and others.

Once the 2018 season ended, New York Yankees GM Brian Cashman talked openly about his disappointment in Gray. In early November, Cashman told the New York Post’s Paul J. Bereswill exactly how he felt:

“We are going to move him if we get the right deal because I don’t think it is going to work out in The Bronx.”

The 29-year-old starter went 15-16 as a Yankee, and his lackluster performance in 2018 earned a demotion to the bullpen. Aaron Boone even left him off the playoff rosters for the Wild Card game and the ALDS.


However, Pickles is a former All-Star and top-three Cy Young finisher (2015). His 3.66 ERA is enough to give teams hope they can turn him around.

New York Yankees

Cashman announcing his intentions doesn’t seem like the best business move, but it’s working out so far. In late November New York Post reporter Ken Davidoff reported that 11 teams were looking into acquiring Gray.

Even though New York clearly wants to shed Gray, they’re not going to take the first deal that comes along.

When the Cincinnati Reds came calling for Gray, Cashman took a page from The Art of the Deal, asking for top-20 prospect Taylor Trammell. There’s no word yet of a more reasonable counter offer, which makes the Padres the current favorite to land Gray.

Gray to the Padres makes sense, as it would send him back to the West Coast where he had his greatest success as a member of the Oakland A’s. The Padres also have a highly regarded farm system, so the Yankees could get a satisfactory return.


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