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2021 Kentucky Derby Prop Bets and Expert Betting Predictions

by Chris Vasile - 4/29/2021

Kentucky Derby contenders will Run for the Roses.

We are now just a few days away from the 147th running of the Kentucky Derby. And for those of you who may not know the history of the Derby, it’s the longest-running horse race in North America, having run every single year since 1875. It took a global pandemic for the Derby to make changes to its run date as it got pushed to Sept. 5, 2020, from its most famous first weekend in May time slot.

This year, there are plenty of storylines surrounding the Derby, and I’ve touched base on almost all of them in the lead up to the big day. The purpose of this article is to show you that there are plenty of ways to bet on the Kentucky Derby, and betting on prop bets is one of my favorite ways to get my action in on the big race.

2021 Kentucky Derby Prop Options

2021 Kentucky Derby – Margin of Victory

Dead Heat +3000, Nose +1000, Head +800, Neck +800, 1/2 Length to 3/4 Lengths +375,

1 Length to 2 3/4 Lengths +200, 3 Lengths to 5 3/4 Lengths +225,

6 Lengths to 7 3/4 Lengths +650, 8 Lengths to 10 3/4 Lengths +725

11 Lengths to 14 3/4 Lengths +1000, 15 Lengths or More +1200.

Analysis: Given the fact that this year’s race is wide open, and the top four or five horses are interchangeable in terms of which one of them have the talent and ability to win, I’m going to bank on this race being a thrilling one that gives us a close finish. In this history of the Derby, the winning length has been one length or less on 42 occasions. The biggest winning margin is eight lengths (four times), so I don’t think that’s going to happen this year.

Pick: ½ Length to ¾ Length +375

What Will the First Quarter-Mile Be?

Over 22.8 Seconds -120

Under 22.8 Seconds -110

Time of the First Half-Mile Be?

Over 46.8 Seconds -110

Under 46.8 Seconds -120

Analysis: I’ve researched the pace scenario. And while pace typically makes the race, this Derby is definitely lacking any real speed threats that will try and steal the race from wire-to-wire. With that said, I do believe this race will be one of the slower ones we’ve seen in a while, so I’ll take the over on both of these options.

Pick: Over 22.80 seconds -120 & Over 46.80 seconds -110

Will the Kentucky Derby Winner Lead Wire to Wire?

Yes +600

No -900

Analysis: This almost never happens, so I’d safely lay -800 with the no option. However, I do not recommend laying this kind of juice… ever.

Where Will the Winning Horse Start?

1-10 Gate +100

11-20 Gate -170

Analysis: If we break down the race by post position, it’s an even split on the four horses I like and where they will be breaking from. I did like Known Agenda’s chances at winning this race until he drew post position No.1. So, he’s off my play list because that’s a very hard post to win this race from. I do like O Besos from Gate 6 and Hot Rod Charlie from Gate 9. I think both of these horses are live long shots to make some noise. On the outside, Essential Quality is the main player from Gate 14, and Super Stock from Gate 18 is another long shot I’d be looking to include in the exotics. With that said, I’m going to try and beat Essential Quality as I don’t think he’ll have any value left come post time, so I’d take a shot with Gates 1-10.

Pick: Gates 1-10 (+100)

Number of Words in the Name of the Derby Winner

1 Word (+700)

2 Words (-300)

3 Words (+190)

Analysis: This prop is a tough one to predict, but if we go on my choices for the above prop, O Besos, Super Stock or Hot Rod Charlie, you can see that two words is what I would lean to if I believed a long shot could win the race. I am very high on Hot Rod Charlie, and I think he’s the best bet to give Essential Quality all he can handle. Other three-named horses are Rock Your World (5/1) Like the King (50/1) and Soup and Sandwich (30/1).  I don’t recommend laying -300 on a horse prop, but I’d be inclined to take the 2 words option.

Pick: 2 Words (-300)

Will 2020 Kentucky Derby Handle Exceed 2019

Yes +100

No -140

Analysis: In a normal year, I’d say probably not because there isn’t much by way of must-see talent in this race. Sure, all the horses are exceptional in their own right, but the hype around this year’s Derby has been tempered a bit. Why I think it has a chance to beat the 2019 handle is because people are sick and tired of this pandemic we are in and there really is nothing else to do. I wouldn’t bet it, but I wouldn’t be surprised either way.

Pick: There are better options on the board.

Will Secretariat’s Record of 1:59.4 be Broken

Yes +1500

No -4500

Analysis: This record is similar to Wayne Gretzky’s point record in the NHL or Cal Ripken’s games played streak in MLB. Nobody is going to beat it for a very long time, if ever, and with no speed threat upfront, the fractions are going to be slow and the finishing time of this race will be well over two minutes.

Pick: No. But don’t ever lay this kind of juice. 

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