Win Win Win Odds to Win the 2019 Kentucky Derby with Picks and Predictions

by Trevor Whenham - 4/17/2019

Some horses have a better chance than others to win the Kentucky Derby on May 2

There are the horses in any Kentucky Derby field that are the obvious strength. And there are the ones that have no place in the field and are easy to toss out. But then there are horses in the middle, ones like Win Win Win this year, who fit somewhere between those two groups. They aren't good enough to be considered a major contender, but if things fall their way and they have a good day they could find themselves in the mix. They are the horses that cause headaches. Can Win Win Win win the Kentucky Derby?

Last race: At the Blue Grass Stakes, Win Win found himself way further back early on than we are used to seeing from him. He was 11th at the first turn and eighth at the second. And he dealt with some early contact that seemed to affect him. But he overcame those issues, steadied himself nicely in the stretch, and charged hard. He wasn't nearly good enough to catch the runaway winner, Vekoma, but he was clearly second best. The Blue Grass was the least-impressive field of the major Derby preps, but the horse showed a fair bit in the solid performance - especially in the face of that early adversity.

Prior experience: The horse started his career at Laurel for his first three starts. He broke his maiden in his first try in November then came back to dominate an allowance race a month later. He was second in a listed stakes before turning three and heading south to Tampa Bay. His first outing there was the Pasco, a very early prep race, and Win Win Win dominated it by seven impressive lengths. That earned him a shot in the Tampa Bay Derby, where he closed strong, finishing third behind Tacitus , who will be among the favorites in the Derby. That set him up for the Blue Grass. It was a solid progression through the spring for the horse, but not one of a major contender. His name may indicate that he is done winning, though - he already has three career wins.

Trainer: Michael Trombetta is a fixture on the Maryland circuit, and he has won more than 1,700 races so far over a long career. But while he is capable of winning a lot of races, those wins only rarely come at the highest levels. His lone breakthrough in Triple Crown races came in the 2006 Preakness when he was second with Sweetnorthernsaint. He is a capable trainer, and he is doing good work with this horse, but he is outclassed by some of the other trainers in this race - not that that always matters.

Jockey: Julien Pimentel had ridden this horse in each of his first four races before being replaced by Irad Ortiz Jr. for the Tampa Bay Derby and the Blue Grass. Ortiz picked up a better ride in Improbable , though, so Pimentel has landed back in the saddle for the Derby. He's making his Derby debut in this race. But he has a whole lot of experience riding for Trombetta - they have combined in more than 1,800 races and won almost 20 percent of them. Pimentel isn't the world's best rider, but he deserved his Derby break before now.

Breeding: Win Win Win is a son of Hat Trick. That sire was bred in Japan and won Grade 1 races in both Japan and Hong Kong. He was a high-level miler. He was brought back to the U.S. to stand at stud, as his sire, 1989 Derby and Preakness winner Sunday Silence, had been in Japan for his career, so his bloodlines were not in Kentucky. Hat Trick had some moderate success, but has moved to Brazil of late, so he isn't a superstar stallion. He was a miler, but his sire ran longer, and an early son, Bright Thought, set a world record at a mile and a half on the turf. There is some stamina here. Win Win Win's damsire is Derby and Preakness winner Smarty Jones, who was a better runner than he has been a stallion. In human terms, both of Win Win Win's grandfathers are multiple Classic winners. There are going to be worse-bred horses in the field.

Odds: This colt went off at 21/1 in the final Kentucky Derby futures pool, which makes him neither a favorite nor a serious long shot. He sits at +2500 in early futures betting at BetOnline.

Can Win Win Win Win the 2019 Kentucky Derby?: Probably not. I'm more hesitant to toss him than some other horses, but he isn't as good as some of the other horses that will be looking to run the same kind of race he will. He might wind up being used in some of the deeper exotics, but he won't be on top of any of them for me.

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