Hamdan bin Rashid Al Maktoum
After winning the inaugural Dubai World Cup on American-owned Cigar to help put the event on the international racing map, Bailey returned the next year to ride for Dubai's home team. He won the second running of the then-$4 million race for Sheikh Mohammed aboard Singspiel, who was running on dirt for the first time. The 1997 edition had to be delayed four days due to torrential rains in the desert. Their lucrative partnership continued the next year when Bailey rode Daylami to a win in the 1998 Man O' War Stakes. Bailey rode Godolphin's Worldly Manner to a seventh-place finish in the 1999 Kentucky Derby, giving up the mount on winner Charismatic, who he had ridden two weeks earlier to win the Lexington Stakes at Keeneland. In 2000, Sheikh Mohammed flew Bailey to England to ride Godolphin Racing superstar Dubai Millennium in the Prince of Wales's Stakes at Royal Ascot after regular stable rider Frankie Dettori was injured in a plane crash three weeks earlier in Newmarket. Bailey consulted with Dettori about the horse, then rode him to an impressive victory. In the winners' circle, Bailey imitated Dettori's trademark flying dismount and the two jockeys hugged. That fall, Bailey also rode Fantastic Light to a win in the Man O'War. Bailey teamed with the Maktoums to win the $6 million World Cup in 2002 on Godolphin Racing's Street Cry, when Dettori decided to ride the stable's Sakhee instead. Almost three months later, Street Cry and Bailey won the Grade 1 Stephen Foster Handicap at Churchill Downs. With Bailey's retirement looming in three weeks, he took a January 7, 1996, mount at Gulfstream Park on Bernardini, owned by Sheikh Mohammed's Darley Stable. Trainer Tom Albertrani told Bailey that Bernardini "will make you postpone your retirement", but Bernardini finished fourth that day in his career debut and Bailey retired as planned. Bernardini then reeled off six straight wins, including the Preakness Stakes, Travers Stakes and Jockey Club Gold Cup, ending his championship 3-year-old season and his career with a second-place finish in the Breeders' Cup Classic to Invasor, owned by Sheikh Mohammed's brother, Sheikh Hamdan bin Rashid Al Maktoum.