David Cone: Cy Young Award winner, 5-time champion
According to baseball-reference.com, 55 players have played on the winning side in at least five World Series, and all nine whose careers crossed into the current millennium were connected to the Joe Torre-era Yankees dynasty, including Hall of Fame locks Mariano Rivera (eligible in 2019), Derek Jeter ('20), and one of this year's likely one-and-done players, Jorge Posada.
The only one of the nine to win an individual regular season award is Cone, the 1994 AL Cy Young winner while with the Royals. The hard-throwing righty was an October staple who pitched for eight postseason teams during his 17-year career (1986 to 2001, '03), starting with the 1988 Mets, for whom he went 20-3 with a 2.22 ERA. Late in the 1992 season, he was dealt to the Blue Jays, whom he helped beat the Braves in that year's Fall Classic; he also led the majors in strikeouts that year with 261, after having led the NL in both 1990 and ’91. A two-year detour to his hometown of Kansas City, with whom he had started his professional career, followed. He won the Cy Young for going 16-5 with a 2.94 ERA during the strike-shortened season, and after being traded back to the Blue Jays and then the Yankees in 1995, pitched for the New York's ’96, ’98, ’99 and 2000 champions; he posted a 2.12 ERA in 29 2/3 innings over his five World Series, and threw in a perfect game in 1999 for good measure.
Cone finished with a career record of 194-126, a 3.46 ERA and a 62.5 career WAR/43.5 peak WAR/53.0 JAWS line, good for 60th among starting pitchers but not quite Hall caliber; he received 3.9% of the vote in 2009.
SI Vault: Masterpiece Theatre (07.26.1999)