The New York Yankees began the 2020 offseason with a bang, signing star pitcher Gerrit Cole to a nine-year, $324 million deal with an out after five years. This guarantees him $36 million per season, shattering Stephen Strasburg’s deal in stature.
However, the path the Yankees took to get to the finish line was unconventional, as they pulled out all the stops to lure Cole to the Bronx. They dipped into their pool of former players; guys Cole looked up to while growing up. Andy Pettite played a massive part in selling the Bomber’s culture to his family and giving him a reason to believe he can win multiple Championship wearing Pinstripes.
The New York Yankees used their biggest piece to solve the puzzle:
While Pettite did play a significant part in inking the deal, owner Hal Steinbrenner was the catalyst behind it all. Before the offseason began, Hal was reluctant to admit the starting pitching rotation needed reinforcements. Still, it seems GM Brian Cashman convinced him Cole would take the team to a different level, and the amount of money he would spend would be paid back 10-fold in Championship runs. Ten years without a World Series appearance can be troublesome for such a historic franchise.
“If the 2020 season was to start tomorrow, I would feel considerably more confident than I did a year ago at this time,’’ Steinbrenner said. “We will have both Severino and Montgomery back. We now know that [Domingo] German can pitch effectively at this level. And we know [James] Paxton can be the guy that we were hoping for when we made that trade. We have [Masahiro] Tanaka, [J.A.] Happ, [Jonathan] Loaisiga, and perhaps [Deivi] Garcia at some point. A very good rotation.’’
“We’re going to be active in the free agent market. I like our rotation right now. As of now, I like our 2020 rotation better than I liked our 2019 rotation…
Just spoke to Scott Boras. Asked the agent what helped make Gerrit Cole choose the Yankees and he said, “ Five conversations with Hal Steinbrenner,” and “Andy Pettitte.” Boras was impacted by Hal’s persistence and Cole was influenced by Andy’s stories about pitching in NY.
— JackCurryYES (@JackCurryYES) December 11, 2019
About one month later, Steinbrenner was playing a pivotal role in bringing Cole the New York after his evasion in 2008 and 2017. An unlikely hero in the negotiations, but one that will go down in history, nonetheless.