Cross emerged as a promising prospect while playing at South Plantation High School in Plantation, Florida, and received multiple scholarship offers from NCAA Division I colleges.[1] However, he was not initially academically eligible and instead played his first two seasons of college basketball with the Miami Dade Sharks.[1] During his sophomore season, he was selected to the All-State Team and named by Basketball Weekly as being among the top junior college transfer candidates.[1] In 1986, Cross was offered a scholarship by the University of Hawaii at Manoa, who had first attempted to recruit him during his high school career.[1] He was required to spend the 1986–87 season at Leeward Community College while not playing basketball to become academically eligible for Hawaii.[1] Cross financially supported himself while taking classes by working full-time as a courier for a legal firm.[1]
Cross made his debut for the Hawaii Rainbow Warriors during the 1987–88 season, and averaged 15.7 points per game.[1] During his senior season in 1988–89, Cross led Hawaii to its first postseason bid since 1974 while averaging 18.6 points per game.[1] Cross was subsequently selected to the All-WAC First Team, while he was named as Hawaii's most outstanding player during both of his seasons with the team.[1][2][3] He gained further attention from NBA teams following a promising showing at an All-Star Game in Japan and earned invites to multiple NBA tryout camps.[1]
Cross' first child, a daughter, was born while he was attending Miami Dade.[1] He married the child's mother, Gwenell, in 1986.[1] His second child, a son, was born during his first season at Hawaii.[1]