What are the best Kentucky Derby bets?

Apr 25, 2018 Dick Powell/TwinSpires.com

Each year, the Kentucky Derby (G1) has a field of 20 horses going a distance of ground that none have ever attempted. Please don't call it a crapshoot since rolling a pair of dice only has 11 possible outcomes.

With 20 horses, it results in 380 possible Exacta outcomes and 6,840 Trifecta combinations. Superfectas are not my thing but there are 116,280 combinations in a 20-horse field. Great race to win; hard race to make money. It is just as important to handicap the field down to who you like as it is to who you don't like since you are going to be forced to leave out legitimate contenders.

I am a Win bettor, but what has happened in the recent renewals of the Derby is that the Win pool gets leveled out. Favorites might be decent odds but the 10th choice is usually an underlay. If you really like someone strong, by all means play him to Win and Place. You'll regret it if you don't and your horse wins without you having the gimmick.

In the 2009 Kentucky Derby, I loved Pioneerof the Nile. He went off as the third choice in the wagering at 6.3-1 so I made a $200 Win/Place bet on him. To protect, I made seven $20 exactas with him second. I even used Summer Bird at 43-1, but did not use Mine That Bird at 50-1. The exacta paid $2.074.80. Ouch!

What I beat myself up over was not the fact that I bet $540 and got back $840 on the place bet (and, yes, I missed the $20 exacta for $20,748), but what really hurt was for another $120, I could have back-wheeled the other 12 runners in $10 exactas and cashed $10,374. Yes, I made $300 on the 2009 Kentucky Derby. But every time I remember the race, it's a bad beat.

If I can narrow the Derby down to two main contenders, and they are high-enough prices, I can bet each to win, place. Then I can wheel them up and down in exactas with about four or five contenders.

I will then take the top two and box them with three others in a five-horse Trifecta box which will cost $30 for 50-cent units. At this point, you hope your top choices run well but gets beat by one of the longer priced contenders.

Finally, I take the top two choices and play them up and down in partial Trifecta wheels. Let's say I like the 1 and 2 to win and the 3, 4, 5, 6 underneath. My 50-cent Trifecta wheels would look like this:

1 with 2, 3, 4, 5, 6 with 2, 3, 4, 5, 6 = $10

2, 3, 4, 5, 6 with 1 with 2, 3, 4, 5, 6 = $10

2, 3, 4, 5, 6 with 2, 3, 4, 5, 6 with 1 = $10

2 with 1, 3, 4, 5, 6 with 1, 3, 4, 5, 6 = $10

1, 3, 4, 5, 6 with 2 with 1, 3, 4, 5, 6 = $10

1, 3, 4, 5, 6 with 1, 3, 4, 5, 6 with 2 = $10

For $60, I can still hit a generous Trifecta. Worst case is the 1 and 2 finish first and second but then I have the Win/Place, Exacta and a good shot at a short Trifecta.

If either of my top two choices win, I should make money.

If either of my top two choices win or place, I have a good chance in the Exactas.

If either of my top two choices win or place, I have a decent chance at the Trifecta.

If my top two choices do not win or place, I still have a chance in the Trifecta box and part wheels.

If none of my horses run well, I am not going to win and move on.