How to Bet the 2019 Tampa Bay Derby

I don’t know if he’s the most likely winner—that’s a tough call—but I do believe that #7 Win Win Win has the most raw talent of any horse entered in the March 9, $400,000 Tampa Bay Derby (gr. II) at Tampa Bay Downs.

The obstacles facing this son of Hat Trick are formidable. Primarily, he’s never run farther than seven furlongs, and there’s no guarantee that he can be effective while stretching out to 1 1/16 miles in this Road to the Kentucky Derby prep race.

And yet, I’d argue that no horse on the Derby trail has shown as much brilliance as Win Win Win. He’s 3-for-4 so far, with his lone defeat coming against the very good colt Alwaysmining in the Heft Stakes at Laurel Park. You can make a case that a poor start and a tough rail trip made the difference between winning and losing that day.

Otherwise, Win Win Win has looked like a star in the making. In a 5 ½-furlong allowance optional claiming race at Laurel Park, he annihilated seven rivals with a breathtaking turn-of-foot in the homestretch, running the fifth furlong in :11.09 and the final sixteenth in :05.69 to power clear and win by 6 ½ lengths. Even at Laurel, which is known for producing fast finishes on the main track, those are fantastic fractions.

Win Win Win was even better in the seven-furlong Pasco Stakes at Tampa Bay Downs in January. Another slow start left him eight lengths off the early pace, but then he unleashed a tremendous rally in the middle of the race, roaring through the second quarter-mile in about :21 2/5 to reach contention. He then swallowed the leaders and pulled away down the lane to win by 7 ¼ lengths in 1:20.89 seconds, breaking the track record.

Win Win Win has come back with some blazing workouts at Tampa Bay Downs, so he seems to be maintaining good form. The question is, can he show the same acceleration going two turns? From a pedigree perspective, there is some hope; his grandsires are the Kentucky Derby/Preakness winners Sunday Silence and Smarty Jones.

The bigger problem might be Win Win Win’s recent habit of breaking slowly, but hopefully he’ll get a good pace in front of him if he does come away sluggishly from the starting gate. There might not be an abundance of clear-cut front-runners in the Tampa Bay Derby field, but there are plenty of pace-pressing types, and the presence of #5 Well Defined should ensure a solid tempo up front. The talented Florida-bred dominated the Sam F. Davis Stakes (gr. III) at Tampa last month in front-running fashion and figures to employ similar tactics on Saturday. #11 Zenden, a stakes-winning sprinter stretching out in distance, should also be forwardly placed.

#4 Dream Maker, a powerful allowance winner at Fair Grounds, and #6 Outshine, who recently returned from a long layoff to win a Gulfstream allowance race for trainer Todd Pletcher, are among the other logical contenders.

I’ll box Win Win Win and Well Defined in an exacta, then key Win Win Win on top of a trifecta while emphasizing Well Defined underneath:

$7 exacta: 5,7 with 5,7 ($14) $2 trifecta: 7 with 5 with 2,4,6,11 ($8) $2 trifecta: 7 with 2,4,6,11 with 5 ($8)

Good luck!