How the Yankees Wooed Gerrit Cole

SAN DIEGO — A courtship that began in 2008 was rekindled on Dec. 3 in a suite at the Fashion Island Hotel in Newport Beach, Calif. The Yankees arrived to the hotel bearing gifts for Gerrit Cole, whom they had drafted out of Orange Lutheran High over a decade earlier before failing to persuade him to forgo his commitment to U.C.L.A.

But this off-season, after becoming perhaps the best pitcher in baseball, Cole was a coveted free agent. And one of the teams he grew up cheering for had made him their foremost priority.

The Yankees brought a gold-colored, home plate-shaped box that had his name and trinkets inside. There were team T-shirts and wristbands and a smart tablet with information an opposing player would not know about the Yankees, like their clubhouse amenities and resources to support players’ families.

The club enlisted a range of officials throughout the organization for their pursuit, from Andy Pettitte, a former Houston Astro and Yankee who won five World Series in the Bronx and was one of Cole’s favorite players growing up, to Hal Steinbrenner, the Yankees’ principal owner. During a four-hour meeting at the hotel with Cole, his wife and his agent, Scott Boras, the Yankees’ contingent — which included Pettitte, General Manager Brian Cashman, Manager Aaron Boone, the assistant general manager Michael Fishman, and Matt Blake, the team’s new pitching coach — attempted to woo the 29-year-old Cole.

“We’re not trying to sell anything,” Cashman said. “We’re just trying to make sure that we educate the player and his family about our culture and everything we are.”

The strategy worked, culminating late Tuesday in an agreement on a record-breaking deal worth $324 million over nine years, making Cole the highest-paid pitcher in major league history and bolstering the Yankees’ status as a favorite to win the 2020 World Series. It was the type of deal reminiscent of the so-called Evil Empire Yankees under Steinbrenner’s father, George — using the club’s deep pockets to attract the most talented players in free agency.

Cole, who helped lead the Astros to the World Series last year in his second season in Houston, was impressed by Pettitte and his stories about pitching and dealing with expectations in New York. Hal Steinbrenner, who couldn’t attend the meeting in Southern California because of a family event, spoke to Cole on the phone and later took a central role in the negotiations.

After the meeting at the hotel, Cole departed, and the discussions continued between Boras and the Yankees contingent over dinner at nearby restaurant, Louie’s by the Bay.

The bidding for Cole did not begin in earnest until Monday, when Stephen Strasburg — another star free-agent pitcher and Boras client — agreed to return to the World Series champion Washington Nationals on what was at the time a record deal: seven years and $245 million.

Then the offers started coming in for Cole, who is two years younger than Strasburg and the more-coveted free agent. Two big-market teams close to Cole’s hometown, Newport Beach, were also in serious pursuit of him.

The Los Angeles Dodgers, who are seeking their first World Series title since 1988, eventually reached an offer of eight years and $300 million, which included deferred payments, according to three people involved with the negotiations who requested anonymity because they were not authorized to discuss them.

The Los Angeles Angels, who have the best player in baseball in Mike Trout but who have failed to reach the playoffs since 2014, also offered an eight-year deal with deferred payments, but just under $300 million, the people said.

But the Yankees, who have not won a World Series since 2009, were willing to go above and beyond. They recognized a need for a top-flight starting pitcher — illustrated by the Nationals’ winning a World Series title by leaning on the aces Max Scherzer, Patrick Corbin and Strasburg.

The Yankees won 103 games during the 2019 regular season primarily because of their potent offense and bullpen. But their starting rotation was plagued by both poor performances and numerous injuries, finishing with a 4.51 earned run average, 15th in the major leagues. And the Yankees believed Cole was the type of person who could put them over the top.

“I can just guarantee a championship-caliber effort on our part, with the sign of the cross from ownership,” Cashman said earlier in the week of the team’s recruitment of Cole.

Cole, whose deal is still pending a physical, could instantly improve the Yankees’ starting rotation, with a right arm capable of 100-mile per hour fastballs. He went 24-6 with a 2.39 earned run average and 373 strikeouts last year, including the postseason. From May 22 through the end of the playoffs, he lost just one game as he put together one of the greatest stretches in major league history, posting a 1.59 E.R.A. and 258 strikeouts over 169⅓ innings. He also has had few injuries.

“A guy that is certainly in the prime of his career,” Boone said on Wednesday morning, adding later, “This is a kind of person that has all the winning intangibles and makeup.”

Cole, in turn, liked what he heard and saw from the Yankees, who separated themselves from their West Coast competition by pushing their offer to nine years. By the third and final iteration of their offer, the deal had no deferrals, included a full no-trade clause and a player opt-out after the fifth year, and set records for overall commitment to pitcher and highest average annual value — beating tTrout’s deal ($35.5 million average annual value).

(The Yankees will owe the Astros draft pick compensation because Cole declined their qualifying offer.)

Cole agreed to his new deal by dinner time on Tuesday. Word leaked within a few hours that Cole was headed to the Yankees.

Boras and his team celebrated in the lobby bar of the Manchester Grand Hyatt, where baseball’s annual winter meetings are happening this week. Cashman and his employees did so at the 40th-floor bar of the hotel.

The Yankees had twice tried acquiring Cole before, in the 2008 draft and in an attempt to trade for him before the 2018 season when he was with the Pittsburgh Pirates. Cashman recently referred to Cole as the team’s “white whale.” On Tuesday night, concluding a courtship over a decade in the making, the Yankees finally had him in their grasp.