There is a small and prestigious group of professional athletes across all sports who have managed to excel both on their respective playing surfaces and in the front office, building winning organizations. Names like Danny Ainge, Jerry West, Steve Yzerman, and Ozzie Newsome are often among the first that come to mind. Yet, for many other NBA legends, including “His Airness,” the transition isn’t always as smooth. Despite storied careers on the court, many former NBA All-Stars find the executive suite a different kind of challenge, one that doesn’t always lead to the same level of success they achieved on the hardwood.