Danny Caldwell’s first Oaklawn stakes victory came with a 9-year-old. Now, Oaklawn’s four-time leading owner bids for a second with another 9-year-old in late-running millionaire Rated R Superstar, who is scheduled to make his 2022 debut in the $150,000 Fifth Season Stakes for older horses at 1-mile Saturday at Oaklawn.

Caldwell won the 2017 Fifth Season with Domain’s Rap, who was making his 9-year-old debut after being claimed for just $10,000 in November 2015 at Remington Park. Caldwell claimed Rated R Superstar for $50,000 last January at Oaklawn and has been rewarded, again, by another member of the elderly equine set.

Rated R Superstar, in eight starts for Caldwell and trainer Federico Villafranco, has bankrolled $298,991. Caldwell recouped his investment when Rated R Superstar finished second in the $500,000 Essex Handicap for older horses last March at Oaklawn. The gelding surpassed $1 million in career earnings in the Essex, was eighth in $1 million Oaklawn Handicap (G2) for older horses last April at Oaklawn, an allowance winner in May at Prairie Meadows and captured the $175,000 Governor’s Cup Stakes Aug. 20 at Remington Park, where Caldwell is the all-time leading owner.

After winning the Fifth Season, then worth $125,000, Domain’s Rap made his final four career starts later in the 2017 Oaklawn meeting. He won a $76,000 allowance race, was third to eventual 2017 Horse of the Year Gun Runner in the $500,000 Razorback Handicap (G3) for older horses, second to eventual 2017 Met Mile winner Mor Spirit in the $250,000 Essex Handicap for older horses and second to Inside Straight in the $750,000 Oaklawn Handicap (G2) for older horses. Inside Straight finished second to Domain’s Rap in the allowance race. Domain’s Rap retired with $880,850 in earnings during a 64-race career.

Domain’s Rap spent most of his career in the allowance and stakes ranks in Illinois before tumbling down the class ladder and being claimed, but Rated R Superstar began his racing career as a promising Triple Crown prospect for nationally prominent trainer Kenny McPeek.

Rated R Superstar, in 2015, finished second in the $150,000 Iroquois Stakes (G3) for 2-year-olds at Churchill Downs, then third in the $500,000 Breeders’ Futurity Stakes (G1) for 2-year-olds at Keeneland. Breeders’ Futurity runner-up Exaggerator won the Preakness in 2016. Rated R Superstar became a multiple Grade 3 winner for McPeek, earning $518,367 in 30 starts before being claimed by trainer Cipriano Contreras for $62,500 in November 2018 at Churchill Downs.

In 18 starts for Contreras, Rated R Superstar earned $363,656. The gelding ran third in the 2019 Razorback before winning the Essex, then worth $350,00, in his next start.

A son of 2008 Oaklawn allowance winner and 2009 champion sprinter Kodiak Kowboy, Rated R Superstar has a 9-10-8 record from 56 lifetime starts and earnings of $1,181,014. He has won from 6 furlongs to 1 1/8 miles. Rated R Superstars is seeking his fifth career stakes victory in the Fifth Season, which has attracted two other millionaires in Snapper Sinclair for Hall of Fame trainer Steve Asmussen and Long Range Toddy (Dallas Stewart). Also entered is Concert Tour, who won the $1 million Rebel Stakes (G2) for 3-year-olds last March at Oaklawn for Hall of Fame trainer Bob Baffert. The colt, unraced since the Preakness last May, is now with trainer Brad Cox.

The projected nine-horse Fifth Season field from the rail out: Thomas Shelby, David Cohen to ride, 122 pounds, 5-1 on the morning line; Rated R Superstar, David Cabrera, 122, 8-1; Snapper Sinclair, Ramon Vazquez, 122, 6-1; Necker Island, Francisco Arrieta, 122, 9-2; Concert Tour, Joel Rosario, 122, 5-2; Atoka, Luis Contreras, 122, 15-1; Long Range Toddy, Jon Court, 115, 10-1; Silver Prospector, Ricardo Santana Jr., 115, 10-1; and Mucho, Florent Geroux, 122, 7-2.

Probable post time for the Fifth Season, which goes as the eighth of nine races, is 3:46 p.m. First post Saturday is 12:30 p.m.

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