2. Gerrit Cole: Nine Years, $324 Million
For every fan who wants to give out $300 million deals to Marcus Semien and Corey Seager like chiclets, keep in mind that Gerrit Cole was this franchise's first -- though, as contract figures throughout the league continue to rise, it'll someday be dwarfed by a free agent deal for, like, Jackson Holliday.
Cole has been an ace since signing in New York, no matter what MLB Network says, and put some of his postseason bugaboos to bed when he put the Guardians to sleep last fall. Huh. Maybe pitching at Fenway Park on a bum hamstring isn't the be all, end all?
Still, this contract will be criticized (rightfully so) if the gopher balls continue to rise, and if Cole's unable to reach the World Series and triumph. The Yankees outbid the field significantly to get their man, a Yankee Fan Today, Tomorrow, Forever. This city that never sleeps won't rest until he's on top of the world.