Pay Billy carries with him the hopes of Maryland racing fans, who watched him develop from floundering maiden to two-time stakes winner, and of Minnesota, where his owners come from. It’s a big test, but he enters on a roll.

5. PAY BILLY (20-1)

Post Position: 5
Color/Sex: Bay colt
Age: 3
Sire–Dam–Damsire: Improbable – Harlington’s Rose – Harlington
Owner: RKTN Racing LLC
Trainer: Michael Gorham
Jockey: Raul Mena
Record: 8 starts: 4 wins, 1 place, 1 show
Earnings: $234,475
Typical Running Style: Press-stalk
Last Raced: April 19, 2025 – Federico Tesio Stakes – Won by 1½ lengths
Note: Carries local hopes after winning Laurel’s two-turn stakes for sophomores
Quote: “It’s going to be an exciting week. We’re looking forward to it.” – Mike Gorham

Pay Billy (20-1) enters the Preakness with momentum and a touch of hometown pride after capturing the Federico Tesio Stakes at Laurel Park. The son of Improbable has quietly put together a solid résumé and will now test much deeper waters on racing’s biggest stage. Trainer Mike Gorham is embracing the moment, and with Raul Mena staying aboard, this press-stalk type figures to sit just off the leaders and hope for a well-timed move. Though facing tougher foes, Pay Billy would make a lot of locals happy if he outruns expectations at Pimlico.

BREEDING

Every horse in the Preakness that has been sold at auction fetched at least $200,000 – except for Pay Billy, who brought a winning bid of $60,000 from RKTN Racing.

Pay Billy is by Improbable out of the Grade 3-winning Harlington mare Harlington’s Rose. Harlington’s Rose didn’t win much – only four times from 34 starts. But she cobbled together a bankroll in excess of $420,000. She was a sprinter, with her best win coming at six furlongs.

Pay Billy is one of three of Harlington’s Rose’s offspring to race and isn’t far from being the richest. That title currently belongs to Espionage, by Into Mischief, who’s made nearly $350,000 and won a couple of minor stakes. Another half-sibling, Wiseacre, by Uncle Mo, retired winless.

Multiple Grade 1 winner Improbable earned over $2.7 million on the track but finished sixth in the 2019 Preakness won by War of Will. In his four-year-old season, he won three Grade 1 races and finished second, to Authentic, in the Breeders’ Cup Classic.

Pay Billy is Improbable’s second richest runner to date. Oddly enough, the richest, Governor Sam, is a turf sprinter. So far, Improbable’s offspring are winning at a 24% clip in dirt routes with Pay Billy having accounted for three of those wins.