How to Bet the 2019 Kentucky Derby

Profile Picture: J. Keeler Johnson

May 2nd, 2019

If you’ve been following all of the 2019 Kentucky Derby coverage , you’re probably aware the scratch of morning line favorite #12 Omaha Beach has thrown my Derby handicapping into disarray.

He was ranked on top in my final Kentucky Derby Top 10. He was the only horse listed as an overlay on my fair odds line. He was ranked as my lone win candidate when I split the 20 Derby starters into four categories for wagering purposes.
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Now I have to regroup, starting with a revision of my fair odds line. The biggest change involves Maximum Security. I’ve slashed his odds from 10-1 to 5-1, making him a clear-cut overlay compared to his morning-line price.

My suddenly optimistic view of Maximum Security stems directly from the scratch of Omaha Beach. I had a strong suspicion jockey Mike Smith would ride Omaha Beach aggressively in the Derby, hounding Maximum Security from an early point in the race. That won't be the case now, and Maximum Security seems increasingly likely to be part of a modest early pace. As we saw in the Florida Derby (G1), Maximum Security can be brilliant when he relaxes on the lead and sprints home through the final three furlongs.

Maximum Security is something of a risky play, because he’s never been seriously challenged and we have no idea how he’ll react if someone engages him in a battle for the lead. But at least he’s fast, with two triple-digit Beyer speed figures under his belt, and he’s won in the mud, so a wet track shouldn’t be an issue.

The other horse I’m now listing as an overlay is #16 Game Winner. I was having trouble envisioning this tried-and-true grinder wearing down Omaha Beach, but the latter’s defection could leave Game Winner in a nice stalking position a few lengths off the early lead, giving him first run at the leaders around the far turn and down the homestretch.

In terms of wagering strategy, my initial plan was to key Omaha Beach on top of the trifecta and superfecta while emphasizing Game Winner underneath. But with the race appearing more wide-open now, I’ll scrap my superfecta plans and focus exclusively on the trifecta, keying Maximum Security and Game Winner on top in equal strength.

I’ll emphasize tickets playing both colts to hit the board, but I’ll also use a wide variety of other runners for second and third place, without endeavoring to split them and use some for third place only. Contrary to popular belief, over the last 15 years or so it has been easier for longshots to finish second in the Derby than third or fourth. The latter two spots are often occupied by well-regarded runners who endure tough trips or just come up short, while longshots who run out of their skin frequently get up for second (think Closing Argument, Golden Soul, Commanding Curve and Lookin at Lee).

To boost the payoff, I’ll also seek to hit the trifecta for higher than the 50-cent base amount. If my preferred combination comes in—Maximum Security and Game Winner on the board, with Improbable or Roadster occupying the other slot—I’ll cash the bet for $3. Similar combinations adding By My Standards and Code of Honor for second and third would trigger a $2 payoff, while any other winning outcome would strike for $1.

$1 trifecta: 7,16 with 5,7,16,17 with 3,5,7,8,13,14,16,17,19,20 ($48) $1 trifecta: 7,16 with 3,5,7,8,13,14,16,17,19,20 with 5,7,16,17 ($48) $1 trifecta: 7,16 with 7,16 with 3,5,13,17 ($8) $1 trifecta: 7,16 with 3,5,13,17 with 7,16 ($8)

Total: $112

Good luck!