Masai Ujiri has been with the Raptors organization since May 31, 2013 when he signed a five year $15 million dollar deal. He was also given a multi-year extension prior to the start of last season.
On the court, the team won three consecutive Atlantic Division titles between 2013-2016 and have made four straight play-off appearances during Ujiri’s reign.
The team’s affiliation with Drake (which was in part spearheaded by Ujiri) has been a success in certain aspects. However, the Drake relationship was supposed to be a major recruiting tool used to help lure big name NBA free agents to Toronto but that relationship has still yet to bare any fruit in that department.