A Horse Racing Expert Breaks Down The Strategy That Helped Him Turn $1,040 Into $435,000 In Tampa’s Pick-5

horse racing feet on turf

iStockphoto / quentinjlang

Michael Iavarone has been around the world of horse racing for years and he’s reached the top. His horse, Big Brown, won the 2008 Kentucky Derby and Preakness Stakes before suffering a defeat in the Belmont Stakes, finishing one leg shy of the Triple Crown of Horse Racing.

Michael’s a bonafide horse racing expert which is what makes this story so interesting to me. If there are so many genuine experts in the field (which there 100% are), then why don’t more of them cash in on huge bets like the one Michael Iavarone just won at the Tampa Bay Downs.

According to Twinspires, Michael Iavarone ‘invested’ $1,039.50 on a Pick-5 sequence in the Tampa Bay Downs’ late Pick 5. After some wild controversy on the track, he won, and he cashed in for $435,029.40!!! He shared his winning strategy over at Twinspires and it’s an interesting read for anyone who has spent time betting the ponies.

Here’s what he had to say about his winning strategy:

“When I play a Pick 5, I really try and find the winner of the grass race. I feel like I have a better feel for grass racing than I do for dirt racing, so I normally try to find a single in one of the grass races and, more importantly, I’m looking for a price,” Iavarone said. “If I don’t see a price to single, I’ll normally wait for another opportunity. I normally like to play these anywhere from $600 to a couple thousand.”

The single on his ticket was Admiralty Pier, who eventually left the gate at odds of 21-1.

“What I liked about the horse is that he’d run well at Tampa before a year earlier,” said Iavarone, referring to Admiralty Pier’s close fifth-place finish in the 2019 Tampa Bay. “Then they shipped the horse to Canada and they were sprinting the horse at Woodbine. His form leveled out and I didn’t think sprinting was going be his game.

“They brought the horse back to Tampa and I noticed the horse ran on dirt the start before this grass race. Knowing Tampa’s dirt course pretty well, I knew that horse would get a lot of conditioning. It’s pretty deep over there. I always felt he was a better grass horse than a dirt horse. I thought he’d like a fast course. It was speed favoring, pretty quick, and felt he had a chance to wire those horses.” (via)

That race was wild, according to Twinspires. It resulted in a photo finish which then led to an objection from an opposing rider. So he reeaaaaaalllllly had to sweat out that leg of his Pick-5.

He goes on to state that there aren’t many Pick-5 tickets that payout nearly half of a million dollars and it’s all about getting the right sequence:

“There are not many Pick 5s that pay $435,000, period,” Iavarone said. “That itself is beyond unique. That’s usually a Pick 6 number.

“It was hard sequence. This is one of those where you better be lucky than good.”

I didn’t want to borrow the entire article from Twinspires where he explains each of his horse choices so you can just follow that link if you’re interested in reading about it. The reality is you’ll need a shit ton of luck and you’ll need to make some educated guesses on a few long shots.