When I play a Pick 5, I really try and find the winner of the grass race.


Big Brown wins the 2008 Kentucky Derby
Big Brown (Reed Palmer/Churchill Downs)

More than a decade after reaching the pinnacle of the sport when his IEAH Stable campaigned in partnership Kentucky Derby (G1) and Preakness (G1) winner Big Brown, Michael Iavarone reached a new peak as a horseplayer on Feb. 8 when purchasing at TwinSpires.com the sole winning ticket of Tampa Bay Downs’ late Pick 5 worth $435,029.40.

Although Iavarone invested $1,039.50 on the sequence, pressing the “All” button in three of the legs, it proved far from an easy win. Not only did Iavarone have to beat two odds-on favorites and sweat out three photo finishes to scoop the pool, but his lone single also had to survive a stewards’ inquiry and a rider’s objection after winning a photo.

Iavarone’s ticket was centered on his opinion in the $175,000 Tampa Bay (G3), a 1 1/16-mile grass race for older horses that was the third leg of the Pick 5.

“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.  

Pick 5 winning ticket at Tampa Bay Downs
(image courtesy of Michael Iavarone)

“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.”

Admiralty Pier led nearly all the way, but no sooner had his number been posted after a prolonged wait to determine a photo finish than the stewards conducted an inquiry and an opposing rider lodged an objection.

“I watched the stewards’ replay, but I kinda never saw where he had done anything,” Iavarone said. “The longer these inquiries go, usually they work against you. [A disqualification] would have been worse than losing the photo.”

When the stewards decided to leave the results stand, Iavarone was 3-for-3 and assured of a winning ticket as he had the fields for the fourth and fifth legs covered. The only question remaining was how much the payoff would be.

Many Pick 5 tickets had already crashed…

…after the first leg when 1-5 favorite Got Stormy finished unplaced in the Endeavour (G3).

“I was surprised to see Got Stormy pop up there, a proven Grade 1 horse,” Iavarone said. “I thought early February was kind of early for this horse, and felt maybe she wasn’t cranked up and was using it as a stepping stone to bigger and better. I felt it was a good opportunity to beat the horse.”

Iavarone used Got Stormy and two others, including Jehozacat, who led wire-to-wire at odds of 16-1. However, that proved a nail-biter as Jehozacat just lasted by a neck over a 10-1 shot Iavarone hadn’t used.

Sole Volante wins the Sam F. Davis Stakes
Sole Volante (SV Photography)

Even more tickets went bust in leg four, the Sam F. Davis (G3), when 7-10 favorite Independence Hall finished second to 5-1 chance Sole Volante.

“I just felt that if you’ve never been over the dirt track at Tampa before, that horse would be vulnerable,” Iavarone said of Independence Hall. “I was playing the field more to beat him than any particular horse in that race, and I knew that would represent a good number of the tickets if that horse was to get beat. I was just hoping first time over Tampa Bay’s course he was beatable.”

When it came time for the last leg, a $16,000 claimer on the turf for fillies and mares, Iavarone was looking at splitting the pool if one of half the field won, or winning it outright if one of the longer prices came through. In the final strides, 12-1 shot Better Yet caught 7-2 chance Itsagimme’s Girl by a neck, leaving Iavarone the biggest winner on the entire Tampa Bay card.

“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.”

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Jules and Michael Iavarone leading Next Shares after the 2018 Shadwell Turf Mile (Coady Photo/Keeneland)