A native of San Francisco, California, Middlebrooks attended St. Ignatius College Preparatory and was a standout player for the Wildcats.
During his freshman year he helped lead them to a West Coast Athletic Conference championship and a berth into the 1985 NCAA Tournament, where Pepperdine would lose in the first round.
[3] The following season, the Waves once again won the WCAC, qualified for the 1986 NCAA Tournament, and lost in the first round.
[2] After his collegiate career ended, Middlebrooks tried out with the Cleveland Cavaliers of the National Basketball Association.
[5] He was not selected in the subsequent NBA draft, and so he carved out a professional career which took him from the Continental Basketball Association to various teams in Mexico, Spain, Cyprus and Argentina.