Nicknamed "Big Dog" and "the Chosen One",[1][2] he played in the National Basketball Association (NBA) from 1994 to 2005 for the Milwaukee Bucks, Atlanta Hawks, Philadelphia 76ers, and San Antonio Spurs.

[3] Robinson attended Theodore Roosevelt High School[4] in Gary, where he started playing organized basketball during the 9th grade.

During his senior season (1990–91), he led the Panthers to an Indiana state basketball championship,[5] winning the final game against Brebeuf Jesuit and their star Alan Henderson; this highly anticipated showdown was captured in The Road to Indianapolis.

[10] Due to struggles with NCAA eligibility, resulting from Proposition 48 which requires minimum academic standards, he had to redshirt for his freshman season.

Along with teammates Cuonzo Martin and Matt Waddell, he led the Boilermakers to a Big Ten Conference Title and an Elite Eight appearance, finishing the season with a 29–5 record and a 3rd overall ranking.

[18] After several trades, one of which had Baker go to Seattle, Robinson teamed with Ray Allen and Sam Cassell, and helped lead the Bucks to several postseason appearances.

On May 11, 1999, Robinson scored 23 points and grabbed 12 rebounds in a narrow 108–107 playoff loss against Reggie Miller and the Indiana Pacers.

In the final game of that series, Robinson scored 24 points, grabbed 7 rebounds, and recorded 4 assists in a losing effort.

[23] Robinson was the second place all-time leading scorer in Milwaukee Bucks history, only trailing Kareem Abdul-Jabbar until surpassed by Giannis Antetokounmpo.

[24][25][26][27] Robinson was traded by Milwaukee to the Atlanta Hawks for Toni Kukoč, Leon Smith, and a 2003 first-round pick on August 2, 2002.

In his tenth overall and only season playing with the Sixers, Robinson averaged 16.6 points and 1 steal per game as second scoring option to teammate, Allen Iverson.

Robinson signed with the San Antonio Spurs on April 4, 2005, to establish an additional veteran shooting presence as the team prepared for the playoffs.

His oldest son, Glenn III, played basketball for the University of Michigan and started for the national runner-up 2012–13 team.

[29][30] Glenn III was the NBA Slam Dunk Contest champion in 2017 when he was with the Indiana Pacers and most recently played for the Sacramento Kings.

Robinson also has a daughter named Jaimie who competes in track and field,[32] As a freshman, she was 2014 Class 2A Illinois High School Association (IHSA) runner-up in the triple jump for De La Salle Institute.

[41] On May 16, 2003, Robinson was convicted in Cook County, Illinois of domestic battery and assault charges involving his former fiancé on July 20, 2002, in her Chicago Heights home.