In December 2007, Randy Levine, president of the New York Yankees, helped re-sign third-baseman Alex Rodriguez to a ten-year contract worth $275 million, which was, and still is, the richest contract in the history of professional sports. For Levine, it was a giant bet, an Empire State Building–size stack of chips on the possibility that A-Rod, by consensus the best hitter and all-around player in baseball, would add to the Yankees’ bulging shelf of championships while mounting a serious campaign to break the home-run record. For Rodriguez, the contract was both a recognition of his immense talent and an outlandish promise to keep. It goes without saying that, over the course of a Yankees tenure that included two MVP years and a world championship, numerous slumps and streaks, and a pair of drug scandals that have come to define his career as much as his talent has, the men would have much to talk about, which they did primarily via e-mail. In the course of reporting the magazine’s December 9, 2013, cover story (“Chasing A-Rod”), I viewed a trove of the electronic correspondence between Rodriguez and Levine, a selection of which is excerpted below.