[3] He played for twelve NBA franchises, most prominently in three stints with the Philadelphia 76ers, in thirteen seasons from 1997 to 2010 after beginning his career with the CBA in 1995.

In his second year as Huskies head coach, they won the 2014 NCAA Division I men's basketball tournament.

[4] His mother, a school teacher and ordained minister, raised him and his older sisters, Vita and Rhonda, by herself.

The team was ineligible for postseason play because of an NCAA ban resulting from a low Academic Progress Rate score several seasons prior.

On April 5, 2014, the Huskies defeated top-ranked Florida in the Final Four national semifinal of the NCAA tournament 63–53.

Connecticut also lost one scholarship for the 2019–20 class, was put on two years' probation, fined $5,000 and received various minor recruiting restrictions.

Ollie was charged with three Level I violations stemming from the following: summer pick-up games that should have counted toward allowable team activities, a video coordinator engaging in impermissible coaching instruction and a booster providing extra benefits to student-athletes.

The extra benefits were provided by a private trainer and included training, lodging, meals and local transportation.

Should a school have sought to hire Ollie before his show-cause order expired on July 2, 2022, it would have had to meet before the NCAA committee on infractions to justify the move.

[11][12] Ollie filed a claim under the university's grievance process, alleging disparate treatment due as his predecessor was retained despite committing NCAA violations.

[13][14] UConn then refused to continue with the contractual grievance process when Ollie filed a separate claim through the courts.

[16] On April 12, 2021, Overtime Elite announced Ollie's hiring as head of coaching and basketball development.

[18] After Vaughn was fired during the 2024 NBA All-Star break, the Nets promoted Ollie to fill the role of head coach on an interim basis.

Although he was only in his second year of coaching, he started with a team subject to sanctions, unable to compete in the NCAA tournament, and still managed to complete the season with a 20–10 record, and followed that with a national championship.