![Anna Wintour (L) and Michael Jordan (R) watch Marin Cilic of Croatia take on Roger Federer of Switzerland during their semifinal match of the US Open at the USTA Billie Jean King Anna Wintour (L) and Michael Jordan (R) watch Marin Cilic of Croatia take on Roger Federer of Switzerland during their semifinal match of the US Open at the USTA Billie Jean King](https://c8.alamy.com/comp/TYPC63/anna-wintour-l-and-michael-jordan-r-watch-marin-cilic-of-croatia-take-on-roger-federer-of-switzerland-during-their-semifinal-match-of-the-us-open-at-the-usta-billie-jean-king-national-tennis-center-in-new-york-city-on-september-6-2014-upimonika-graff-TYPC63.jpg)
Anna Wintour (L) and Michael Jordan (R) watch Marin Cilic of Croatia take on Roger Federer of Switzerland during their semifinal match of the US Open at the USTA Billie Jean King
![Michael Jordan watches Marinko Matosevic of Australia play Roger Federer of Switzerland at the US Open Tennis Championships at the USTA Billie Jean King National Tennis Center in New York City on Michael Jordan watches Marinko Matosevic of Australia play Roger Federer of Switzerland at the US Open Tennis Championships at the USTA Billie Jean King National Tennis Center in New York City on](https://c8.alamy.com/comp/TYPAX5/michael-jordan-watches-marinko-matosevic-of-australia-play-roger-federer-of-switzerland-at-the-us-open-tennis-championships-at-the-usta-billie-jean-king-national-tennis-center-in-new-york-city-on-august-26-2014-upijohn-angelillo-TYPAX5.jpg)
Michael Jordan watches Marinko Matosevic of Australia play Roger Federer of Switzerland at the US Open Tennis Championships at the USTA Billie Jean King National Tennis Center in New York City on
![Former NBA Player Michael Jordan attends the evening tennis match between Roger Federer of Switzerland and Marinko Matosevic of Australia during the 2014 U.S. Open at the USTA Billie Jean King National Former NBA Player Michael Jordan attends the evening tennis match between Roger Federer of Switzerland and Marinko Matosevic of Australia during the 2014 U.S. Open at the USTA Billie Jean King National](https://c8.alamy.com/comp/2EY1WFY/former-nba-player-michael-jordan-attends-the-evening-tennis-match-between-roger-federer-of-switzerland-and-marinko-matosevic-of-australia-during-the-2014-us-open-at-the-usta-billie-jean-king-national-tennis-center-in-the-new-york-city-borough-of-queens-ny-on-august-26-2014-photo-by-anthony-beharsipa-usa-2EY1WFY.jpg)
Former NBA Player Michael Jordan attends the evening tennis match between Roger Federer of Switzerland and Marinko Matosevic of Australia during the 2014 U.S. Open at the USTA Billie Jean King National
![NEW YORK, NY - AUGUST 26: Michael Jordan watches Roger Federer of Switzerland defeat Marinko Matosevic of Australia during their men's singles first round match on Day Two of the 2014 US NEW YORK, NY - AUGUST 26: Michael Jordan watches Roger Federer of Switzerland defeat Marinko Matosevic of Australia during their men's singles first round match on Day Two of the 2014 US](https://c8.alamy.com/comp/KPGCJB/new-york-ny-august-26-michael-jordan-watches-roger-federer-of-switzerland-KPGCJB.jpg)
NEW YORK, NY - AUGUST 26: Michael Jordan watches Roger Federer of Switzerland defeat Marinko Matosevic of Australia during their men's singles first round match on Day Two of the 2014 US
![Michael Jordan watches Marinko Matosevic of Australia play Roger Federer of Switzerland at the US Open Tennis Championships at the USTA Billie Jean King National Tennis Center in New York City on Michael Jordan watches Marinko Matosevic of Australia play Roger Federer of Switzerland at the US Open Tennis Championships at the USTA Billie Jean King National Tennis Center in New York City on](https://l450v.alamy.com/450v/kpg719/new-york-ny-august-26-michael-jordan-watches-roger-federer-of-switzerland-kpg719.jpg)