Strickland had a solid but not spectacular career at DePaul University. He played only 3 years before going pro and in his last year averaged 20 points game.

He was drafted in the first round by the New York Knicks with the 19th overall pick. The pick was a curious one as the Knicks had drafted Mark Jackson the year before. The two however co-existed and Strickland wound up having a solid rookie season for the Knicks.

The Knicks traded Strickland half way through his second season to the San Antonio Spurs. With the Spurs Strickland flourished averaging 14 points and 8 assists. But he was always be remembered by Spurs fans for him poor play in the playoffs against the Trailblazers which cost the Spurs the series.

He got injured his second year with the Spurs and missed time but continued to have solid performances for the Spurs, but playoff success once again alluded them. The next season Strickland was in a contract dispute and missed the first 23 games of the season before finally signing.

The contract dispute the season prior soured both parties on their relationship and Strickland left and signed with the Portland Trailblazers. Strickland would have some of his best years with the Blazers including a career high 19 points a game in 1995. The Blazers however never seen any playoff success despite making it every year Strickland was there.

Strickland played 4 highly productive years for the Blazers before they traded him to the Washington Bullets for Rasheed Wallace. Strickland would help the Bullets turn things around and in 1997 they made their first playoff appearance in nearly a decade. The next season Strickland had arguably his best season as he averaged 19 points and a league leading 11 assists per game.

The Bullets continued to struggle after their 1997 playoff appearance and Strickland became displeased with the way the organization was heading. He asked for and was granted a release in 2001 and promptly returned to the Portland Trailblazers. He lasted only the remainder of the 2001 with the Blazers as a backup to Damon Stoudemire before signing with the Miami Heat.

The last four years of his career was spent between 5 different teams, mostly as a backup and several stints lasted just a few days. He did play the entire season as Miami’s starting point guard before signing with the Timberwolves for one season. The 03-04 season was split between Orlando and Toronto and he finished his NBA career with the Houston Rockets in 2005.

Strickland is currently working as an assists coach with the University of Kentucky.

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