During an 18-year career in Major League Baseball (MLB), he played from 1975 to 1992 for six different teams, most notably the New York Yankees with whom he won back-to-back world titles against the Los Angeles Dodgers.

Mainly, he appeared on Baseball Tonight and provided updates during Monday and Wednesday night September network telecasts.

He was traded with Dock Ellis and Ken Brett from the Pirates to the Yankees for Doc Medich on December 11, 1975.

He later played for the Los Angeles Dodgers (1989–90), Oakland Athletics (1990), and Milwaukee Brewers (1991), finishing his career with the New York Mets in 1992.

Though the ball bounced to Willie Wilson, third base coach Mike Ferraro waved Randolph home.

Wilson overthrew U L Washington, the cut-off man, but George Brett was in position behind him to catch the ball, then throw to Darrell Porter, who tagged out Randolph in a slide.

TV cameras captured a furious George Steinbrenner fuming, hollering and swearing immediately after the play resulting in him being restrained by police when he tried to gain access to the field.

Later that year, Randolph and the A's won the American League pennant, but were swept by the NL-champion Cincinnati Reds in the World Series.

[3] Tommy John, Randolph's teammate with the Yankees, called him the "stabilizing influence" and "the club's quiet leader".

[4] Randolph was a Yankees base and bench coach for 11 seasons, interviewing intermittently for managing jobs with other teams.

Holding a seven-game first-place lead in the NL East with only 17 games to play, the Mets finished 5–12 and lost the division to the Philadelphia Phillies, who went 13–4 in the same timespan.

[8] In 2008, Randolph's job security steadily decreased after a disappointing start to the season and inconsistent performance through mid-June.

Although he was one of the three finalists, the job went to Ken Macha, and Randolph was given the bench coach position, which he held until November 2010.

On November 23, 2010, Randolph was named as the final piece to Buck Showalter's coaching staff for the 2011 Baltimore Orioles.

On November 26, 2012, it was announced Randolph would be the third base coach in the World Baseball Classic for Team USA.

"[4] Randolph delivered the commencement address to Fordham University's 2007 graduating class, of which his daughter Ciara was a member.