Sources told ESPN.com this week that the Raptors have interest in talking with Jackson about the Pat Riley-style role he craves in charge of a team's basketball operations. ESPN.com reported last week that Jackson, after nearly two seasons in retirement, is itching to return to the NBA next season, preferably in a role similar to Riley's in Miami that allows him to oversee both the basketball department and the coaching staff or perhaps as a high-level consultant such as Jerry West in Golden State.
Leiweke is a major player in the sports industry and Jackson is very familiar with his work in Los Angeles, where Leiweke helped get the Staples Center built for the Los Angeles Lakers and Clippers as well as the NHL's Kings. Leiweke also has a longstanding working relationship with Lakers executive Jeanie Buss, Jackson's fiancee.
It'll definitely be interesting if it comes to fruition. It's difficult to argue against Jackson being the greatest coach in NBA history, but through the years there has been the suggestion that he benefitted greatly from inheriting teams that were more or less ready built for success. It's also been pointed out from time to time that Red Auerbach not only coached and built the Celtics Dynasty of the 50s and 60s, but also helped put together other championship teams in Boston in later years, strictly as an executive. For Jackson, it would be a different challenge to the situations he's been in before and certainly another feather in his cap if he can succeed in such a role.