In this Monday, Oct. 14, 2019 file photo, Gerrit Cole...

In this Monday, Oct. 14, 2019 file photo, Gerrit Cole throws on the field at Yankee Stadium during the ALCS. Credit: AP/Kathy Willens

It is not the overriding question Yankees general manager Brian Cashman asks himself when he pursues any player — let alone a star such as Gerrit Cole — but it is high on the list:

Can the player handle New York?

There are more than a few examples of players brought in by the Yankees over the years who could not, of course. Cautionary tales such as Javier Vazquez, Kevin Brown, A.J. Burnett and Sonny Gray, just to name a small handful of the train wrecks the Yankees have acquired through free agency or trades, are never fully out of Cashman’s mind.

Needless to say, the can-handle-New-York-box for Cole was checked off by Cashman, and the Yankees reached agreement with the 29-year-old righthander on a record nine-year, $324 million contract last Tuesday.  

Actually, Cole checked off that box in Cashman’s eyes years earlier when the Yankees chose him in the first round of the 2008 draft out of Lutheran High School (Calif.) and he instead went to UCLA on scholarship.

In other words, not signing with the Yankees showed Cashman that Cole, expected to be officially introduced at a news conference this week, could handle playing for them.

“I would use the examples of how he's willing to just bet on himself,” Cashman said during last week’s winter meetings in San Diego. “So I don't think many high school kids being drafted in the first round by their childhood dream team, with financial components coming their way that far exceeded what a college scholarship would be worth, would say, ‘I'm going to college because it'll all work out and I'm going to bet on myself.’ ”

That supreme self-confidence continued into his professional career. Cole perfectly set himself up for the record-setting payday for a pitcher he ultimately received.

“Fighting through six years of service time through two franchises, Pittsburgh and Houston, and willing to say, ‘I'm going to not be open to an extension and I'm going to see what it's going to be like in free agency for myself and put myself in a position to have a free choice,’ ” Cashman said. “I mean, those are very competitive decisions. So I would say those are examples of someone who's talking the talk and then shows you can walk the walk.”

Cole walked the walk in his walk year, too, dealing with the pressure of playing for his next contract as well as anyone has in recent memory. He went 20-5 with a 2.50 ERA for the Astros in 2019 and finished second to teammate Justin Verlander in the American League Cy Young Award voting. In his last 22 regular-season starts, he was 16-0 with a 1.78 ERA and the Astros went 20-2.


Cole, 94-52 with a 3.22 ERA in his big-league career with the Pirates and Astros, went 4-1 with a 1.72 ERA in five starts in the 2019 postseason. Overall, Cole is 6-4 with a 2.60 ERA in 10 postseason outings.

“There's no guarantee for anybody on any level,” Cashman said, still talking about evaluating players, Cole in particular, and their ability to perform in New York. “But you try to have your takeaways from the people that coach them, that played alongside of them, and see how they react in the crazy environment of, obviously, playoff baseball and World Series baseball. And listen, he has checked every box thus far.”

Cashman led a Yankees contingent — one that included manager Aaron Boone, new pitching coach Matt Blake and special adviser Andy Pettitte — to Cole’s native California the week before the winter meetings to make an organizational pitch to the ace. Not that he entered the meeting with any doubts, but Boone quickly reached the conclusion that Cole will be just fine in the cauldron of the Bronx.

“His mindset,” he said. “Everything that we [saw]. We got to spend a lot of time together and really learn about him and him about us. Everything suggests this is a guy that would thrive anywhere but, I’m confident, especially in New York.”

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