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2021 Kentucky Derby Long Shots: Expert Advice and Betting Tips for Finding Value

by Chris Vasile - 4/26/2021

Shackleford, the Preakness Stakes Winner

The countdown is now at less than one week until the Kentucky Derby. And while I’ve written enough words about the favorites of the race, I do think this Debry is one of the more wide-open races we’ve seen in a while. Last year, it was wide open, but that was because the race was in September and the horses that ran had extra time to mature and adjust their schedule so they were peaking at the right time.

This year, the Derby is back in its normal spot – May 1, 2021, and it’s going to be won by the best horse and the horse that can find a peak effort at the right time. The betting board is wide open outside of the top horse (Essential Quality). However, when you look at the history of the Derby, favorites are typically not a good bet. I’ve circled three Kentucky Derby long shots that I believe are worth playing a win ticket on given the right price. Perhaps most importantly, if you are an exotic player, these horses are key to have in your exacta, trifecta and superfecta tickets.

Mandaloun (+2000)

If you’re looking for a major player to crack the trifecta and light up the tote board, it could be Mandaloun. That is, of course, if you can forgive him for his latest race where he didn’t fire off well in the Louisiana Derby despite going off as the heavy 6/5 favorite. I think I can find a way to draw a line and forget that race as the winner, Hot Rod Charlie, is one that I really like this weekend to make some noise, and the third-place finisher, O Besos, is a horse I think has an outside chance. Mandaloun is a Bay colt that is out of Into Mischief and Brooch. He will be ridden by Florent Geroux and is trained by one of the hottest trainers on the planet right now, Brad Cox. The reason why I believe he could be sitting on a big race is that he’s bred to go long as he’s from a Derby-winning sire and a Belmont-winning damsire. The best path to the winner’s circle will be to stay out of trouble and sit close to the pace and then use his speed and stamina to get the distance.

Midnight Bourbon (+2500)

Midnight Bourbon is a bay colt bred by Tiznow and Catch the Moon and is owned by Winchell Thoroughbreds LLC and trained by Steve Asmussen. He will be ridden by Mike Smith, and the hall of fame jockey won’t be shy about pressing this colt up near the front of the pack. Midnight Bourbon has excellent speed and stamina in his bloodlines, and he’s posted excellent speed figures in all three of his prep races at Fair Grounds racetrack. To show for his efforts, he’s got a second, third and first since January 2021. From what I’ve seen and heard about the goings on around Churchill this weekend, Midnight Bourbon has been putting out bullet works and looks extremely sharp considering he’s a horse that’s been lightly raced so far in his short career. He will definitely be worth a look for a win ticket, and he will definitely be in my trifecta ticket.

O Besos (+3300)

Horse racing is a very hard industry to make a profit in. The best horses are usually the favorites and the returns are limited, while the long shots are hard to pick because there are usually a bunch of them in every race. When I look to back a long shot that I believe has a chance, I have to see a pattern of improvement coming into the race I want to be him in. O Besos has that improvement pattern. And I believe if he continues to trend upwards, a peak performance could be on the horizon in the Derby. O Besos is a chestnut colt that is trained by Greg Foley for owners Bernard Racing LLC, Tagg Team Racing and West Point Thoroughbreds with Marcelino Pedroza in the saddle. O Besos has only five races to date, and he’s won two of them, with one third-place finish. What I like is the speed figure improvement he’s shown. In five starts, he’s gone from 60 to 78 to 83 to 88 to 96. If he is sitting on a peak performance in the Derby, he should hit around 101 or better, and that will have him right up there with the favorite. O Besos is the son of former Kentucky Derby winner Orb and he should enjoy the distance very much. Hopefully for me, he goes overlooked on the day and we can get him at a nice price to possibly win or boost up the exactor or trifecta payouts.

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