The goal between now and Derby Day is to figure out how to maximize my coverage and opportunity based on the opinions I will have developed on the 20 Derby entrants.
by Justin Dew
Favorites have won the last five Kentucky Derby. In 2016, the top four betting choices ran 1-2-3-4 in order. As a bettor who likes to use the Derby as an opportunity at a life-changing score (or at least a year-making score), an edition dominated by low odds horses usually means a bad day for me. But that doesn’t have to be the case, and to my credit I feel I have learned from past mistakes.
Take 2004, for example. Smarty Jones and Lion Heart were the top two betting choices in the Kentucky Derby, and they ran 1-2 in order of favoritism. Imperialism finished 3rd at a modest 10-1. But the fourth-place finisher, Limehouse, helped to light up the tote board by contributing to a $41,000 (for $2) superfecta at odds of 41-1. The trifecta only paid $987. So let’s say you liked the two favorites to run 1-2, and then used every horse that was under 20-1 the 3rd spot, with all in 4th. As a $2 play, that’s $380 and a return of over $41,000…..with the two favorites running 1-2 in order!
Easy game, right?
Not so fast. Last year, I liked Always Dreaming as a top win candidate, but wouldn’t have had Battle of Midway or Lookin at Lee even WITH the ALL button (joke). In 2013, Orb was my top pick, and I used runner-up Golden Soul on all tickets, but didn’t match them up with the rest of the superfecta.
Thus, one of my goals for this year is to make sure I am in a position to cash a big ticket if I am right about the most likely winner and also right about a longshot who runs big. And I need to do it economically. But at the same time, how many horses can I confidently eliminate from superfecta consideration? Six? Seven? Can I trim down my selections near the top of the ticket and allow myself to use the ALL button? Do I need to just single my top pick in the 1st spot in lieu of a win bet on him, and then spread heavily underneath?
Maybe I’m looking at something like 1x13x12x11 at a cost of $1,716 (that’s one horse keyed on top over the other 13 in spots 2-4). If one of the seven horses that I eliminate from superfecta consideration runs 4th, then I guess I can just accept the fact that I didn’t deserve to cash. Or maybe the thing to do is play my top two in 1st and demand that one of my top five or six longshots runs somewhere in the 2nd and 3rd spots, with the other logical horses in there as well. So, something like this:
1st: Top two horses
2nd: Top six longshots
3rd: Top seven overall (including the top two)
4th: Top seven plus top six longshots
So that’s 2x6x6x10, for a cost of $720. And then I play it with longshots only in 2nd and 3rd at a cost of $600, followed by using the top seven in 2nd with just the longshots in 3rd for another $720.
So overall, I would spend more on the superfecta that way, but I’d have my top two on top instead of just a single horse. And in exchange for having that extra coverage on top, I must have at least one of my longshots run 2nd or 3rd, with a big payday coming my way if I’m right about the winner and the non-super-contenders, AND I get more than one one my longshots in the 2-4 spots.
With the 1x13x12x11 approach, I could easily envision a scenario where I hit the superfecta but lose money. See: 2016. But with the “demand a longshot” approach, my top pick could win, spots 2-3 could be filled by logical horses, one of my longshots could run 4th, and I lose. Again, that’s the price (in this example) of using two horses on top.
Or…maybe I try this…..
Use my top two in first, trim it down to three longshots, and leverage the ALL button.
1st: Top two horses
2nd: Top three longshots
3rd: Top seven overall
4th: ALL
That would run me $612, plus another $612 when I move the longshots into 3rd and the top seven into 2nd, plus another $510 when I play it this way….
1st: Top two horses
2nd: Top three longshots
3rd: Top six longshots
4th: ALL
The $510 play gives me a big score if my longshots run 2nd and 3rd, with some extra coverage in 3rd.
I am not after bragging rights. And having been very lucky in recent years to cash some very large tickets at the track, I am not excited by the prospect of winning a few thousand dollars on Derby Day. Apologies if anyone doesn’t like the way that sounds. But I don’t want to see another $75,000 superfecta pass me by. I feel like I need to be willing to spend the money to hit it.

Justin Dew (Left) and AGOS Founder Rich Nilsen (Right)
The goal between now and Derby Day is to figure out how to maximize my coverage and opportunity based on the opinions I will have developed on the 20 Derby entrants. And I am willing to use all or most of my bankroll to take a swing at that payday. Because if someone guaranteed me I could double my bankroll on the Kentucky Derby, I wouldn’t sign up.
Now, if my Derby bankroll is $2,000, and the horse I like is 12-1, maybe the thing to do is abandon the entire approach that I just spent the last hour writing about and simply bet to win.
I have a lot of thinking to do.