Randolph played for the Los Angeles Dodgers from 1989 to 1990, the Oakland Athletics in 1990, the Milwaukee Brewers in 1991, and the New York Mets in 1992. He was the manager of the New York Mets from 2005 to 2008 and a coach for the New York Yankees from 1994 to 200, the Milwaukee Brewers from 2009 to 2010, and the Baltimore Orioles in 2011. Randolph won two World Series championships as a player in 1977 and 1978 and four more as a coach in 1996 and from 1998 to 2000. He served as the New York Yankees co-captain from 1986 to 1988 and was a six time All-Star and won the Silver Slugger Award in 1980. In 2013 Randolph joined ESPN as a postseason baseball analyst.