The list starts off with a tie between 17 — yes, 17! — players who have won the World Series five times. So, we’ll start with Derek Jeter, the face of the Yankees franchise for most of his 20 seasons in the Bronx.
As a great player on a great team, Jeter had many opportunities to win the World Series, as he was always in the postseason. In fact, he is the all-time leader in postseason games, runs scored, hits, total bases and strikeouts.
He played in six World Series — winning four — before the age of 30 but won only one after turning 30. His best performance came in the 2000 World Series versus the Mets when he hit .409 en route to being named World Series MVP.