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.