NEW YORK -- As the Yankees waited for word from Gerrit Cole's camp at the Winter Meetings last week, general manager Brian Cashman said that he would have no trouble resting his head upon his pillow, knowing that the organization had done everything within its power to land its top target.

Clearly, the Yankees were confident in a nine-year, $324 million offer, but they had also done their homework. While the staggering dollar total momentarily left the right-hander speechless, it was the Yanks’ resourceful selection of Italian wine during an earlier meeting that exhibited the organization’s attention to detail.

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“One of the vintages that they brought was the exact same vintage from the anniversary dinner that my wife [Amy] and I had in Florence,” Cole said. “I was a little bit on my heels. I remember trying to stay focused through the meeting and not think about booze the entire time. I still couldn't figure it out.”

When a contingent of Yankees executives met with the Coles and agent Scott Boras two weeks ago in Newport Beach, Calif., manager Aaron Boone presented the coveted hurler with bottles of 2004 and 2005 vintage Masseto merlot, which is rated as one of the finest red wines in the world and retails for about $800-$900 each.

"To see the look on him and Amy's face, it was great," Boone said. "It was something that I think carried some sentimental meaning to them, so I think he was a little perplexed about how we figured that out. We give Lou Cucuzza all the credit for that.”

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Cucuzza, the club’s longtime visiting clubhouse manager, knew of Cole’s affinity for fine wines from numerous conversations during Cole’s previous Yankee Stadium visits with the Pirates and Astros. Cucuzza relayed that tip to traveling secretary Ben Tuliebitz, who passed it along to Cashman.

“I always come into Lou’s office when I’ve got nothing to do and kick my feet up on the table. We just talk about stuff,” Cole said. “I was showing him some pictures of a meal that we ate in a cellar in Florence and there's a picture of a bottle of Masseto on the table. He asked me what the bottle was, and … it's definitely my favorite bottle. I did the Ancestry thing and I’m like 35, 37 percent Italian, so a top-notch bottle of Masseto is close to my heart.”

The Yankees brought more to the 4 1/2-hour meeting than just vino, including a preloaded iPad that answered many of Cole’s questions about playing in New York. Once the session had concluded and the Yankees headed for the airport, Cole found himself mystified by their perfect wine selection.

“When I came home, I was trying to grind it,” Cole said. “I was telling Amy, ‘How the [heck] did they pull that off?’ There are not very many people in the world that know that that's my favorite wine -- and now there are, so feel free if you have an allocation to send it my way.

“But I swear to God, I laid my head down at like 11:30 at night to try to go to sleep. I didn't sleep much after that night, but then I literally flew back up and I was like, ‘Lou! Lou!’”