Selected in the second round of the 1989 NBA draft, he played the first eight seasons of his career with the Portland Trail Blazers, followed by stints with the Phoenix Suns, Detroit Pistons, Golden State Warriors, and New Jersey Nets.

[2] On February 5, 2007, Robinson's number "00" was retired at Gampel Pavilion during halftime of a UConn basketball game against Syracuse as part of the "Huskies of Honor" ceremony which recognized personal accomplishments of 13 former players and 3 coaches.

Robinson won the Sixth Man of the Year Award in 1992–93 after averaging 19.1 points, 6.6 rebounds and a career-best 1.99 blocks per game.

[4] Following Game 4 of the 1992 Western Conference finals against the Utah Jazz, Robinson performed a victory dance that he later told press was named the "Uncle Cliffy".

[17] Robinson was a contestant in the 28th installment of the American reality television series Survivor (filmed in 2013 and broadcast the following year).

[39] The team also included Kenny Anderson, Vin Baker, Craig Hodges, Doug Christie, Sleepy Floyd, Charles D. Smith, and four "streetballers".

[42][43] During his time in the NBA, Robinson used cannabis to help relieve pain and anxiety, and to avoid the undesirable side effects caused by pharmaceutical drugs.

[41] Robinson appeared in the 2019 Netflix film Grass Is Greener, which examines the history of cannabis prohibition in the United States.

[45] His son Isaiah Robinson played basketball for the Jefferson High School Democrats in Portland and for the Houston Baptist Huskies.

[46] Robinson suffered a stroke in March 2017 that paralyzed the left side of his body, but he soon recovered much of his arm and leg movement.