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In the late 1990s and early 2000s, the New York Yankees emerged as Major League Baseball’s Evil Empire. Not only was the ball club winning, but they were also rolling in dough; anytime a big-name free agent hit the open market, Brian Cashman and George Steinbrenner were waiting with a blank check. While the franchise has dialed things back recently, the Yankees of old recently emerged and signed pitcher Gerrit Cole to a massive contract.

It can take more than just money to convince a free agent to sign on the dotted line, though. So how did the Yankees manage to land Gerrit Cole?

How Gerrit Cole became an MLB star

Gerrit Cole established himself as a dominant pitching prospect during high school, inspiring the New York Yankees to select him in the first round of the 2008 MLB draft. Despite the club’s interest, however, Cole never negotiated; instead, he chose to attend college and enrolled at UCLA.

After three seasons with the Bruins, Cole was ready for the show. The Pirates picked him first overall in the 2011 draft, and the pitcher joined the Pittsburgh system. He quickly climbed through the minor league ranks, making his MLB debut in 2013.

In January 2018, the Pirates traded Cole to the Houston Astros; the pitcher quickly found his feet in Texas and went 15-5 with a 2.88 ERA during his first season in the America League. His improvement didn’t stop there, however. In 2019, his stats improved across the board. Cole finished the season 20-5 with 2.50 ERA and a .895 WHIP; he also led the league in strikeouts, strikeout percentage, and strikeouts per nine innings.

How the New York Yankees won a charm offensive

Based on his dominant past two seasons, Gerrit Cole was one of the free-agent market’s major prizes. Unsurprisingly, the Yankees brought out the big guns for their charm offensive.

While Cole grew up in California—a fact which surely buoyed the Los Angeles Angels and Los Angeles Dodgershe grew up as a New York Yankees fan. He even attended a few games in the old Yankee Stadium, watching players like Derek Jeter and Mariano Rivera. Recently, one of the greats from that era personally came calling.

During the negotiation process, Brian Cashman visited Cole and his wife, Amy. When the Yankees general manager arrived, however, he wasn’t alone; manager Aaron Boone, new pitching coach Matt Blake and special adviser Andy Pettitte were also at the door. Apparently, Petitte’s tales of pitching New York resonated with Cole, while owner Hal Steinbrenner won over agent Scott Boras with his persistence. When your favorite childhood team comes calling and offers you a massive amount of money, it’s simply hard to say no.

Gerrit Cole is exactly who the New York Yankees needed

While it’s tough to say that the Yankees are truly struggling, the franchise hasn’t been hitting the heights that they are accustomed to. Despite winning the AL East last season and reaching the playoffs in three straight seasons, that’s not good enough for the historic franchise; in fact, it’s been a decade since they’ve even appeared in the World Series.

For all of their star power and bullpen talent, the Yankees have lacked a consistently dominant starting pitcher; each fall, they were outdone by another team’s ace, including Cole himself during his time with the Astros.

During his playing career, Andy Pettitte always came up clutch in the big moment. By helping bring Gerrit Cole to the Bronx, he might have added another win to his Yankees resume.