When the Yankees brass met with Gerrit Cole for the first time, they brought Andy Pettite with them, to ensure arguably the league’s best pitcher that they were, in fact, serious about signing him.
Pettite was not only in good standing with Cole, but he was also a player he looked up to growing up, making the meeting even more influential. However, Pettite wasn’t the little trick that won over Cole. It was bottles of 2004 and 2005 Masseto Merlot.
This was the very wine that Cole and his wife Amy enjoyed during an anniversary in Florence. What a nifty little trick the Yankees exploited to convince Cole they were pursuing the man, and not just the player. Fast forward several weeks later, and the Bombers now have a rotation consisting of Cole, Luis Severino, James Paxton, Masahiro Tanaka, and more.
When super-agent Scott Boras first told Gerrit of the Yankees’ offer, the look on his face was as deep as the Mariana Trench.
“I didn’t say anything like for a few seconds, and he goes ‘G, are you there? You’re supposed to be f***ing screaming.’ I was like, ‘Yeah, I was just a little taken aback.'”
The in-depth studying of Cole and the little details the Yankees staffers picked up along the way helped them seal the deal, but the two wine bottles were the catalyst for Cole, who had never seen a team present that much care for a player before. There was never a chance owner Hal Steinbrenner and GM Brian Cashman were going to let him get away for the third time.