Build Perfect Exotic Kentucky Derby Tickets

The Kentucky Derby brings opportunities to cash big tickets for little wagers. Our expert shows how to create those exotic betting slips.

The 2018 Kentucky Derby wasn’t the chalkiest finish in that decade, but it was in the discussion. You had 5-2 Justify, 9-1 Good Magic, and 7-1 Audible going 1-2-3. Those folks holding 50-cent trifecta tickets walked to the window and cashed a $70.70 wager.

Not bad? Well, no. It wasn’t bad. But some lucky/astute/blessed/pick-your-adjective-here bettors went one spot deeper on their tickets, added Instilled Regard to a $1 superfecta, and literally glided to the betting windows. That’s where a tax form and a $19,618.20 payday awaited them.

So, what was the difference? What turned a $70.70 trifecta into the price of a good used car or once-in-a-lifetime vacation? Well, the not-insignificant factor that Instilled Regard—the last horse to get into the 2018 Derby—went off at 85-1. He was the longest shot in the field.

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More Big Paydays

Fast-forward two years, to the 2020 pandemic Derby. Authentic wins that September Derby at 8-1. Tiz the Law, the 3-5 favorite, finishes second. That $2 exacta paid $41.40, barely enough to cover a happy-hour bar tab. But add 46-1 Mr. Big News to a $1 trifecta, and you collected $1,311.80, plenty enough for a nice weekend getaway.

Let’s go to 2017. Always Dreaming, your 9-2 favorite in a deeply talented Derby field, takes the roses. Third favorite Classic Empire at 6-1 anchors the superfecta in fourth. But sandwiched in between that chalk was 33-1 runner-up Looking At Lee and 40-1 third-place finisher Battle of Midway. This explains how you get a $16,594.40 payout on a $2 trifecta and—wait for it—$75,974.50 payday on a $1 superfecta.

One more. We go back to 2014, where California Chrome wins the Derby at 5-2, bringing you a $7 payoff on a $2 ticket. But add 37-1 Commanding Curve to a $2 exacta, and you’re collecting $340. Put 8-1 Danza on the back end of a $2 trifecta and that payoff jumps 10 times—to $3,424.60.

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You get the idea. Constructing Kentucky Derby vertical exotic tickets—exactas, trifectas, and superfectas—is an art form that can produce mind-boggling paydays. You’ve got a 20-horse field full of prospects, suspects, and everything in between. The key is to figure out which long shots have a shot and which long shots don’t.

And most years, someone carrying double-digit odds is going to hit the board. The odds dictate it. Nine times between 2012 and 2021, a horse going off between 26-1 and Instilled Regard’s 85-1 landed in at least the superfecta. Five times: Mandaloun (26-1 in 2021), Country House (65-1 in 2019), Looking at Lee, Commanding Curve and Golden Soul (34-1 in 2013), the horse crossed the finish line second.

Country House was promoted to the winner’s circle in 2019 after Maximum Security was disqualified for interference. Mandaloun earned his Derby title nine months after the late Medina Spirit was taken down for failing a drug test.

Horses like Battle of Midway, Mr. Big News, Instilled Regard, Commanding Curve, Looking at Lee and Golden Soul weren’t likely to win. But what separates them from the longshots who have no shot?

Mike Shutty, author of the Super Screener, identified a few factors that come into play when you’re trying to isolate the eye-popping longshots who can blow up the tote board and send you skipping to the window.

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Form Cycle

How does a horse look coming into the first Saturday in May? Did they progress in every Derby prep? It’s OK for a horse not to win its last Derby prep; those who do won’t carry the pinball machine odds you want here. And the last two horses to cross the finish line first: last year Medina Spirit and Authentic two years ago finished second in their final Derby prep. But you want to see progression in terms of form and speed.

Career Aces

Shutty illustrates that every one of those nine bombers came into the Derby with five or six races on the CV. Horses like Justify, who came in with only three starts, and this year’s Santa Anita Derby winner Taiba (only two), usually carry low odds because of the Bob Baffert factor. Shutty points out it’s tough to get into the Derby with only three starts unless you’re a superhorse—in which case you won’t have eye-popping odds anyway (see Justify and likely Taiba this year).

Horses with a strong foundation of five to six starts by May of their 3-year-old season often have the experience to handle a 20-horse free-for-all like the Derby.

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Closers

Here’s the great Derby paradox. Since the points era began in 2013, pacesetters and pressers have won every Derby save one: Orb’s 2013 victory was the last closer to cross the finish line first.

But while front-end and tactical speed is the ticket to the winner’s circle, your path to a monster ticket is often a closer who finds their way onto the board at a big price. This category includes Mr. Big News, Country House, Instilled Regard, Looking at Lee, Commanding Curve and Golden Soul. It also includes Went The Day Well, who finished fourth at 30-1 in 2012, the year before the points system was instituted.

A lot of this comes down to riding skill and luck; for a closer to hit the board, they have to stay out of trouble—often easier said than done—and often go wide to pick off tired horses in the stretch.

Which leads to …

Breeding

Those tired horses in the stretch often fall victim to one—or both—of two factors: they couldn’t handle the pace or they didn’t have the genes to run 1 ¼ mile. Stamina is the great equalizer here, horses bred to run long distances are your go-to’s here. Check the breeding, especially on the sire’s side. You want to see a sire, damsire, or grandsire with distance in the blood.

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