Willie Randolph's journey through Major League Baseball began when he was drafted by the Pittsburgh Pirates in 1972. However, it was with the New York Yankees that he truly established himself as a second baseman. Randolph was traded to the Yankees in December 1975, a move that would define much of his playing career. Known for his defensive skills and keen eye at the plate, Randolph quickly became a fixture in the Yankees' lineup.

During his tenure with the Yankees, Randolph played a crucial role in the team's success. He was part of the Yankees' World Series-winning teams in 1977 and 1978. His ability to get on base and his defensive prowess made him an integral part of the Yankees' infield. Randolph was selected to six All-Star teams during his time in New York, reflecting his status as one of the top second basemen in the league.

Randolph's career with the Yankees spanned 13 seasons, during which he became known for his consistency and leadership on the field. In 1986, he was awarded the Silver Slugger Award, recognizing him as one of the best offensive players at his position. His tenure with the Yankees ended after the 1988 season when he signed with the Los Angeles Dodgers as a free agent.

After leaving the Yankees, Randolph continued to play in the major leagues for several more years. He spent the 1989 season with the Dodgers before moving on to the Oakland Athletics in 1990. With the Athletics, Randolph made another World Series appearance, although the team fell short against the Cincinnati Reds. He then played for the Milwaukee Brewers in 1991 and finished his playing career with the New York Mets in 1992.

Following his retirement as a player, Randolph transitioned into coaching and management. He returned to the Yankees as a base coach in 1994, a position he held for over a decade. His experience and knowledge of the game made him a valuable asset to the coaching staff, and he was part of the Yankees' coaching team during their late 1990s dynasty, which included four World Series titles.

In 2005, Randolph took on a new challenge as the manager of the New York Mets. His managerial career began with promise, as he led the Mets to a National League East title in 2006. The team came within one game of reaching the World Series, losing to the St. Louis Cardinals in the National League Championship Series. Randolph's tenure with the Mets ended in 2008, but his time as manager was marked by a return to competitiveness for the franchise.

Throughout his career, both as a player and a manager, Randolph was respected for his baseball acumen and leadership qualities.