Michael Jordan

With Phil Jackson's contract expiring, the pending departures of Scottie Pippen (who stated his desire to be traded during the season) and Dennis Rodman (who would sign with the Los Angeles Lakers as a free agent) looming, and being in the latter stages of an owner-induced lockout of NBA players, Jordan retired for the second time on January 13, 1999.
On January 19, 2000, Jordan returned to the NBA not as a player, but as part owner and President of Basketball Operations for the Washington Wizards. Jordan's responsibilities with the Wizards were comprehensive. He controlled all aspects of the Wizards' basketball operations, and had the final say in all personnel matters. Opinions of Jordan as a basketball executive were mixed. He managed to purge the team of several highly paid, unpopular players (such as forward Juwan Howard and point guard Rod Strickland), but used the first pick in the 2001 NBA Draft to select high schooler Kwame Brown, who did not live up to expectations and was traded away after four seasons.
Despite his January 1999 claim that he was "99.9% certain" that he would never play another NBA game, in the summer of 2001 Jordan expressed interest in making another comeback, this time with his new team. Inspired by the NHL comeback of his friend Mario Lemieux the previous winter, Jordan spent much of the spring and summer of 2001 in training, holding several invitation-only camps for NBA players in Chicago. In addition, Jordan hired his old Chicago Bulls head coach, Doug Collins, as Washington's coach for the upcoming season, a decision that many saw as foreshadowing another Jordan return.