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Trainer Shug McGaughey won the first Kentucky Derby of his career on Saturday. (USATSI) 

Shug McGaughey has achieved numerous superlatives throughout his Hall of Fame career -- an Eclipse Award for trainer of the year, nine victories in the Breeders’ Cup and a win in the Belmont Stakes.

But until Saturday, the Lexington native had never won The Kentucky Derby. On an overcast day at Churchill Downs, McGaughey finally achieved his lifelong goal, as Orb won his fifth consecutive race under a near-perfect ride from jockey Joel Rosario.

“It means everything to me,” McGaughey told Kenny Rice of NBC, as he fought back tears. “I always dreamed of this day.”

Rosario, who also won the first Derby of his career, darted to the outside to avoid traffic on the final turn, overtook Normandy Invasion in the middle of the stretch and held off late-charging longshot Golden Soul to win by 2 1/2 lengths. Orb crossed the wire in 2:02.89, a relatively fast time for a sloppy track.

Orb, the co-favorite with Revolutionary at 6-1, paid $12.80 to win. Revolutionary closed quickly to finish third just ahead of Normandy Invasion. Golden Soul paid $38.60 to place while Revolutionary paid $5.40 to show. The 16-4 exacta paid $981.60.

In the weeks leading up to the race, McGaughey described Orb as the most improved horse in his illustrious career. Last September in an allowance at Belmont, Orb acted up in the gate and closed slowly to finish fourth -- more than 22 1/2 lengths behind winner Tizracer. Orb followed it up with another fourth-place finish in an allowance at Aqueduct in November.

But McGaughey began to gain confidence in the son of Malibu Moon in February when he upset highly-regarded Violence in the Fountain of Youth. Orb then defeated a strong field in the Florida Derby in March that included Its My Lucky Day and Shanghai Bobby. It was only then that McGaughey felt he had a legitimate shot of winning his first Kentucky Derby.

Under blazing fractions, Mike Smith took Palace Malice to the lead in a first quarter-mile of 22.57. Palace Malice remained on the lead around the first turn, running the half in 45.33 seconds -- the fourth-fastest time in Derby history. At that point, Orb drifted near the back of the pack and led only three horses in the 19-horse field. Rosario, though, waited patiently to make his move and received one on the final turn when he took Orb six-wide to break free.

“Early in the race I wanted him to relax,” Rosario said. “I said hopefully he can go faster than that. I was saying maybe I was too far back, but it was so easy."

The victory was also the first Derby win for Orb co-owner Ogden Mills Phipps. In the annals of horse racing, the Phipps family is considered royalty in the sport. In 1936, the family sold Seabiscuit for $8,000 to California car dealer Charles Howard to make room in their crowded stable. Seabiscuit defeated War Admiral in a race dubbed the “Match of the Century,” and went on to win 1938 Horse of the Year honors.

More than three decades later, Ogden Phipps won a famous coin toss with Penny Chenery that gave him the choice of two foals sired by Bold Ruler. Phipps chose a filly out of Hasty Matelda, leaving Chenery with an unborn foal out of Somethingroyal. The bright red chestnut colt, Secretariat, won the 1973 Belmont by 31 lengths and is arguably the greatest horse in the history of the sport. 

Previously, McGaughey’s best shot to win the Derby came in 1989 when his horse, Easy Goer, finished second behind Sunday Silence. After losing the Preakness Stakes to Sunday Silence in a pulsating stretch duel, the Phipps-owned horse ruined Sunday Silence’s Triple Crown hopes with a win in the Belmont. McGaughey was inducted into the National Museum of Racing and Hall of Fame in 2004. 

"My deepest debt of gratitude always has been and always will be to the Phipps family,” said McGaughey during his induction speech. "My affiliation with the Phipps family is one of the great highlights of my life. I wouldn't be here without them."

It could have been a historic afternoon for a pair of jockeys. Kevin Krigger, aboard Goldencents, was bidding to become the first African-American jockey to win the Derby in more than 100 years. Beset by the sharp pace, Goldencents had nothing left down the stretch. Krigger eased the winner of the Santa Anita Derby up in the final furlong and finished 17th, more than 49 lengths behind Orb.

Rosie Napravnik, meanwhile, looked to become the first female jockey to win the classic for 3-year-olds. Napravnik made a late bid to catch Orb on fast-closing Mylute, but ran out of distance and finished fifth by 3 1/2 lengths. 

Oxbow, with three-time Derby winning jockey Gary Stevens aboard, finished sixth. Stevens rode in his first Derby since coming out of retirement four months ago. Lines of Battle from Ireland finished seventh, denying European champion trainer Aidan O'Brien the victory. A European horse has never won the Derby. 

Keep your eye on horse racing by following Matt Rybaltowski on Twitter@mattrybaltowski.