KEY POINTS

  • The Yankees and Gerrit Cole signed a nine-year $324 million pact
  • At the first meeting, the Yankees offered a gift of two bottles of fine Italian wine
  • One was Cole's favorite bottle, a gesture that sold the pitcher on the Yankees

The New York Yankees signed Gerrit Cole to a record-shattering nine-year $324 million contract this week, capturing their white whale in the process. For a historic free agent signing like this, the Bombers had to pull out all the stops and one small detail really helped their case: fine Italian wine.

The Yankees drafted Cole out of high school but the hard-throwing righty chose college instead. Then, after the southern California native joined the Pittsburgh Pirates, the Bombers tried to trade for Cole but the Bucs chose the Houston Astros as trade partners.

However, GM Brian Cashman and his team finally landed their white whale this offseason by pulling out all the stops. That includes one inspired detail from the first meeting between the Yankees and the Cole camp, including his agent Scott Boras.

Houston's Gerrit Cole allowed only one run on three hits over seven innings to silence Washington batters and help the Astros defeat the Nationals 7-1 on Sunday in game five of the World Series Houston's Gerrit Cole allowed only one run on three hits over seven innings to silence Washington batters and help the Astros defeat the Nationals 7-1 in Game 5 of the World Series. Photo: GETTY IMAGES NORTH AMERICA / Patrick Smith

In that meeting, Yankee manager Aaron Boone presented Cole two bottles of fine Italian wine, 2004 and 2005 vintage Masseto merlot. Those are two of the world’s most coveted red wines and retail for around $800 to $900 each.

Why were these bottles of wine so special to Cole? Well, one is the same bottle that he and his wife Amy enjoyed during their anniversary dinner in Italy. Cole said of the act,

“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. 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.”

Much of the credit for dropping the right-hander’s jaw goes to Yankees visiting clubhouse manager Lou Cucuzza. He and Cole spoke numerous times during visits the pitcher made to Yankee Stadium during his time with the Pirates and Astros.

In one conversation, Cole showed Cucuzza a photo of the anniversary dinner and relayed the fact that the Masseto is his favorite bottle. After Cucuzza learned this, he simply relayed the information upstairs until it reached the ears of Brian Cashman.

The New York Yankees may not be finished with their offseason business as the club is known to want to move J.A. Happ’s contract to lessen their luxury tax bill burden for the 2020 season. The Bombers are currently well over the $208 million threshold and maybe subject to the largest taxes in MLB history after next year.