TwinSpires user wins nearly $750,000 on Kentucky Derby Super High 5

One lucky Ashland, Kentucky native celebrated a monumental win on the Kentucky Derby Super High 5 that paid nearly $750,000 after 80-1 longshot Rich Strike crossed the wire first in the 148th Run for the Roses.

The 30-year-old TwinSpires user employed the strategy of boxing a couple of longshot Derby horses with a few frontrunners in their Super High 5 ticket, then “just crossed my fingers,” after they placed the wager on the TwinSpires app.

The approach payed off handsomely, but the savvy bettor did not realize their ticket had cashed until days later, when they got a phone call from Steve Pallardy, the VIP concierge at TwinSpires.com.

In accordance with federal tax laws, the bettor’s winnings — a whopping $741,018.90 — were taxable and, thus, not released immediately to their account. “I was at work (when I got the phone call), and I was kind of in shock. … our owner, he’s really big into horses, so I called him and let him know, and he was pretty excited.”

While the young punter has experience betting on horse races and has frequented Keeneland for more than a decade, their Derby win was by far the biggest of their life, so far.

Their second-biggest win came just a day before the first Saturday in May, when the Kentuckian hit the Super High 5 on the Kentucky Oaks, won by Secret Oath.

“I won the Super High 5 for like $7,000, so I gave (the Super High 5) another shot on Saturday,” said the handicapper. “Really this past weekend was the first time I’ve ever played (a Super High 5). I normally play just a (superfecta) box or a (trifecta) box.”

Needless to say, the Super High 5 savant will continue to try their hand at pentafecta wagers for the foreseeable future after such incredible beginner’s luck. But as far as how their life will change after winning three-quarters of a million dollars, they say not much will be different.  

“I’m still just going to do my normal day-to-day,” they said. “Maybe go on a nice, expensive golf trip with my buddies, but other than that, nothing (big planned).”