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Picking the Kentucky Derby Winner
Southern Stories

Picking the Kentucky Derby Winner

Picking the Kentucky Derby Winner
Apr 27/18

Picking the Kentucky Derby Winner Posted by: Aaron Stearns | 0 Comments

With the 144th renewal of "The Greatest Two Minutes in Sports" fast approaching, Bourbon & Boots tapped renowned professional handicapper Scott Copeland to share with the Bourbon & Boots family his tips for picking Derby Winners. So here is our advice from Scott on the best odds of being in the money on that glorious day in early May.  Enjoy, share, and best of fortune. 

Picking the winner of the Kentucky Derby is probably the biggest challenge a handicapper can face — maybe with the exception of a $3,000 claimer at Evangeline Downs in South Louisiana. Last time my partners and I visited Evangeline Downs we had to pool our money to buy a 16-ounce Mountain Dew on the way out of town. Sad but true. That being said, here’s my best advice on picking a Kentucky Derby winner. I’ll be back for the Preakness. Crow is a dish best served hot.

Don’t bet the horse with the best race coming up to the Derby. A common mistake is betting the horse that ran the fastest race last time out. 3-year olds are young developing horses. They’re getting better or getting worse each time out. Choose a horse that’s coming up to a big race as opposed one that just ran his best one. The betting public is generally one race behind.



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Bet a fresh horse. You want a horse with experience but not all of it in the last couple of months. Look for a horse with a solid 2-year old campaign and some useful prep races, but with them spread out with a few weeks between each one and none in the past three weeks.

Find a horse with a successful, experienced trainer. Preparing a horse for the Derby is one of the toughest challenges a trainer ever faces. He’s asking a horse to run farther than it ever has, in probably the biggest field he’s ever run. There are a lot of variables to weigh in. Too many inexperienced trainers and owners will do everything they can just to have a “Derby” horse. They’re just damn happy to be there and enjoy the spotlight. Winning would just be icing on the cake as opposed to the main objective.

Bet the jockey? Not a big factor. All of these jockeys are good or they wouldn’t be here. Remember the jockey rides the horse and not the other way around. When they switch I’ll reconsider.

Look for a horse with a middle or outside post position. It’s so easy to get in trouble in that first turn. When the thundering herd of 20 or so horses hit that first turn it resembles the doors opening at Walmart on Black Friday and they all want to get close to the rail for the shortest trip. Horses with posts toward the outside have less chance of getting banged around like a ping pong ball. The exception to this is a stretch running horse with no early speed. These horses can afford to hang back and let the others enjoy the brawl. Ferdinand came from last to first in winning the 1986 Kentucky Derby from the one hole.

Look for a horse with tactical speed. Everyone loves a stretch runner but few of these types actually win the Derby. There are just too many horses to weave through when making their stretch run. It’s really easy for them to get tied up in traffic, and they are usually way over-bet. Look for one that can settle just a few lengths off the early leaders as opposed to those coming from way back. Every once in a while one of these stretch runners will come out of the clouds to win, but betting them is a losing proposition.

If all else fails…just bet the gray horse. Seemed to work for my Grandmother. And remember, never bet a horse whose jockey has a flashlight and road map in his back pocket.

Bourbon & Boots is a southern lifestyle brand, integrating artisan inspired and maker quality craftsmanship into rare, unique, unusual personalized gifts for the person that has everything. Come visit us if you are looking for vintage gifts or seeking cool gift ideas.  



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