Derek Jeter debuted in the Major Leagues in 1995, and the following year he won the Rookie of the Year Award and helped the Yankees win the 1996 World Series. Jeter was also a member of championship-winning teams in 1998, 1999, 2000, and 2009. In 2000, he became the only player in history to win both the All-Star Game MVP Award and the World Series MVP Award in the same year. He is the all-time Yankees hit leader, passing Hall of Fame member Lou Gehrig in 2009.

George Herman Ruth, Jr., best known as "Babe" Ruth and nicknamed "the Bambino" and "the Sultan of Swat", has been named the greatest baseball player in history in various surveys and rankings, and his home run hitting prowess and charismatic personality made him a larger than life figure in the "Roaring Twenties". Ruth was the first player to hit 60 home runs in one season (1927), setting the season record which stood until broken by Roger Maris in 1961. Ruth's lifetime total of 714 home runs at his retirement in 1935 was a record, until first surpassed by Hank Aaron in 1974. Unlike many power hitters, Ruth also hit for average: his .342 lifetime batting is tenth highest in baseball history.

Paul O'Neill won five World Series while playing for the Cincinnati Reds (1985–1992) and New York Yankees (1993–2001). In a 17 year career, O'Neill compiled 281 home runs, 1,269 runs batted in, 2,107 hits, and a lifetime batting average of .288. O'Neill won the American League batting title in 1994 with a .359 average, and was also a five-time All-Star, playing in 1991, 1994, 1995, 1997, and 1998.

Lou Gehrig, nicknamed "The Iron Horse" for his durability, played his entire 17-year baseball career for the New York Yankees (1923-1939). Gehrig set several major league records. He holds the record for most career grand slams (23). Gehrig is chiefly remembered for his prowess as a hitter, his consecutive games-played record. his career was cut short by amyotrophic lateral sclerosis (ALS), now commonly known in the United States and Canada as Lou Gehrig's disease. Over a 15-season span from 1925 through 1939, he played in 2,130 consecutive games, the streak ending only when Gehrig became disabled by the fatal neuromuscular disease that claimed his life two years later.

Joe Torre managed the New York Yankees from 1996-2007. The Yankees reached the post season each year and won ten American League East Division titles, six American League pennants, four World Series titles, and overall compiled a .605 winning percentage. With 2,326 wins, he presently ranks 5th in Major League Baseball all-time managerial wins.