Phil Jackson, who on Sunday told reporters that he’s retiring, led the Chicago Bulls to their first NBA title 20 years ago.

Everything about Jackson’s background suggests a man who has learned to weigh the warring impulses inside him and pursue a system of beliefs and behavior that eludes precise characterization. Compared to most coaches, he comes across like a philosophy professor, a little soft, a little trippy, a little abstract. But put him outside the athletic world, and he would probably come across like an ex-jock or a coach—competitive and driven. Jackson is comfortable on his philosophical tightrope, reaching out to touch something over here, then something way over there, straddling two worlds, listening to all sides, getting along with everyone.