Two-time Kentucky Derby-winning trainer Doug O’Neill’s entries Legends of War and Stubbins finished one-two in the Thursday’s Grade 3, $500,000 Nevada State Bank Franklin-Simpson Stakes at Kentucky Downs in Franklin.

Legends of War, a 23-1 longshot, paid $49.40 to a $2 win ticket, and a $1 exacta with 10-1 Stubbins delivered a $218 return.

Although Legends of War had utilized off-the-pace tactics in winning his last start, an allowance at Del Mar, he was actively involved from the start in the Franklin-Simpson. He broke well under Rafael Bejarano, shot to the lead with a quarter-mile in 23.44 seconds and a half-mile 47.37, and left his 11 rivals behind in the stretch on his way to 1¾-length victory. He was hand-timed racing 6½ furlongs on a firm turf course in 1:16.83.

Stubbins rallied from midpack, pulling two lengths clear of third-place Uncapped while no threat to the winner. The latter edged by a head even-money favorite Archidust, who settled for fourth.

Large payoffs extended beyond the O’Neill pair. With Uncapped overlooked at 85-1, the 50-cent trifecta paid $2,341.35 and the 10-cent superfecta that included the public choice returned $9,570.90.

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It took Gentle Ruler 12 starts and more than a year and a half of competition to win her first race, but relatively little time to rise to the level of becoming a stakes winner at the $500,000 purse level.

Thursday on closing day of the RUNHAPPY Meet at Kentucky Downs, the filly did just that, winning the most lucrative race of her career, the $500,000 Ramsey Farm Stakes by a half-length over longshot Lantiz. The victory, her fifth of 2019, marked her third stakes triumph of the year, following earlier victories in the Grade 3 Robert G. Dick Memorial at Delaware Park and the Keertana Stakes at Churchill Downs.

Under a patient ride from Chris Landeros, her sole jockey in six races this year, Gentle Ruler rallied from a bit farther off the pace than usual, settling in seventh early before falling as far back as eighth. Then, upon hitting the long Kentucky Downs stretch, she kicked into gear, advancing to fourth with an eighth of a mile remaining and then taking charge thereafter. She surged past runner-up Lantiz in the final sixteenth, and third-place finisher Gaining could not close the gap on the final pair, finishing another half-length farther back.

Rounding out the field were Lemoona, Sea Dream, Coco Channel, Venina, Over Thinking, Maroubra and Coachwhip. Na Pali Spirit was scratched.

The winner, a 4-year-old daughter of Colonel John, was timed covering 1 5/16 miles on firm turf in 2:12.73, about a half-second off the stakes record of 2:12.16 set by Al’s Gal in winning the 2016 Ramsey Farm.

The $500,000 Ramsey Stakes was worth $291,400 to the winner, running her total earnings to $643,453 for owner Morsches Stable, who trainer Ian Wilkes credited for their patience with the late-developing Gentle Ruler.

It was the fourth win of the meet for Wilkes, which tied him with Joe Sharp and Wesley Ward for leading trainer.