How to bet the Kentucky Derby

The Kentucky Derby’s arrival on Saturday sneaked up on much of sporting America, those who don’t subscribe to the Daily Racing Form, understand the mathematical components of a Beyer Figure or know Bob Baffert from Bob Saget.

So we’re speaking here to the casual horse player, the one who is above picking based on the name but too lazy to research breeding costs and past record on dirt.

Throwing $100 on the race makes the most exciting two minutes in sports a bit more exciting. So here’s a casual guide — from an admitted non-expert — on how to spread around $100 of bets to perhaps take home a bit of milk money.

The Kentucky Derby is always a maze for handicappers. The favorite has won six of the past eight races, and there’s a heavy favorite in this race: No. 14 Essential Quality, which as of Friday afternoon was 3-5.

Betting Essential Quality to win is the gambling equivalent of rooting for your bond investments to go up in real time. So here’s a few creative ways to approach the race and attempt to cash a few tickets on Saturday evening.

LOUISVILLE, KENTUCKY - APRIL 29:  Essential Quality runs on the track during the training for the Kentucky Derby at Churchill Downs on April 29, 2021 in Louisville, Kentucky. (Photo by Andy Lyons/Getty Images)
Essential Quality runs on the track during training for the Kentucky Derby at Churchill Downs on Thursday. (Photo by Andy Lyons/Getty Images) (Andy Lyons via Getty Images)

Bets with the favorite need to include some value, which is why the key to making some money on Saturday will be identifying the crew of longer-odd horses that could come home.

We really like No. 1 Known Agenda, the Todd Pletcher horse with odds that have ballooned to 19-1 because of the rail draw. No horse has won from the No. 1 slot since 1986 — and only two have finished in the top 3. But Known Agenda is a horse that would be 6-1 with a better draw, so this is the best value to go with any Essential Quality bets.

The smattering below are with the assumption that Essential Quality will factor on the board. And they’re bet with the hope to make money around Essential Quality hitting the board.

Exacta Box with Known Agenda, Essential Quality and No. 9 Hot Rod Charlie

$10 Exacta Box 1-14: Cost $20

$5 Exacta Box 14-9: Cost $10

$5 Exacta Box 1-9: Cost $10

Total exactas: $40

Trifecta box: Known Agenda, Essential Quality and Hot Rod Charlie

$2 1-14-9: Cost $12

Trifecta box: Essential Quality, Hot Rod Charlie and No. 8 Medina Spirit

$2 14-9-8: Cost $12

Trifecta box: Essential Quality, Hot Rod Charlie and No. 10 Midnight Bourbon

$2 14-9-10: Cost $12

Total tris: $36 (others tempting to throw in are No. 12 Helium and No. 7 Mandaloun)

There’s a certain satisfaction that comes with landing the Derby winner. If you are going to make one solo win bet, the best value on the board is Known Agenda. The haul is tough from the inside, but spend the remaining $24 on a win bet for Known Agenda. If he goes off around 20-1, that’s a nice bounty.

Best of luck.

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