Best Kentucky Derby Prop Bets

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When it comes to the Kentucky Derby, there has been a very clear evolution in how intricate wagers can be, and how you can almost bet on any type of outcome on Derby day. We have really moved far beyond just picking a winner or a second-place finisher and moved into head-to-head wagers, bets on racing fractions, length of victory, as well as bets like how many Tweets President Donald Trump will make. Although I tend to find myself trying to rationalize and come up with quantifiable numbers to support my bet, who knows what will happen after three Mint Julep’s and being down $300 before the actual race even begins?

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Here are three of my favorite proposition wagers for the Kentucky Derby:

How many lengths will be winner win by? Over 1.5 (-160), or Under 1.5 (+120)

The Kentucky Derby has been decided by less than one length on 42 occasions. On the opposite end, the Derby has been won by four lengths or more 23 times.

In this year’s run for the roses there seems to be a lot of speed horses entered, or at least horses that tend to favor the front end. With a lot of vying for early positioning, a potential pace duel might ensue upfront. If that is the case, then it tends to benefit horses that are sitting just off the speed, and gives a fair shot for some of the deep closers to run down the frontrunners in the stretch.

The most likely case scenario for this bet to cash would be for faster fractions upfront and a bunched-up finish at the wire. In a field as competitive and closely matched as this one, there is a lot of value in taking the underdog option for the margin of length victory.

Will any horse win two of three Triple Crown Races? No (-175), or Yes (+135)

The odds on this sure have changed since Justify became the 13th Triple Crown winner in history. Since 2002 there have been many near misses – six – with War Emblem, Funny Cide, Smarty Jones, Big Brown, I’ll Have Another, and California Chrome.

Triple Crown winners tend to come in bunches with three winners in the 1930s, four in 1940s, and three in the 1970s. This trend seems to be really be factored in to the odds of this wager, and the recency bias of Justify capturing the bid last year.

With the Kentucky Derby field as wide open as it has been in years, and with no overwhelming favorite – cash on an easy proposition wager this weekend and bet the “No.”

The Last Place Saddlecloth Number Will be? Odd (-200), or Even (+160)

This number seems to overvalue the fact that the longest shot on the board draws post 15. Although there are two 50-1 morning-line runners, the Japanese horse #15 Master Fencer will likely go off at higher odds than that at the call to the post.

Despite who performs or underperforms based on their odds, the most likely last-place finisher is a runner who records a DNF or has to pull up. This can often happen due to unforeseeable circumstances and is something you cannot handicap for. Assuming that the race is run smoothly, five of the 10 runners at 20-1 odds or higher will be breaking out of a gate with an even saddlecloth number. At +160, that seems like a lot of value to take a 50/50 proposition bet.

Good luck this weekend, and enjoy the “most exciting two minutes in sports!”

Special Kentucky Derby Prop Bet Bonus – Picks from BlackJack Fletcher

Will There Be a Triple Crown Winner? No (-700)

The horses in this field are simply too close in terms of talent in order for one to truly separate themselves. There are a lot of very talented horses in this year’s field, but not a truly transcendent one. Lay the juice on the no.

Over/Under 1.5 Lengths Margin of Victory in Kentucky Derby: Under (+120)

We have seen Game Winner in neck-and-neck battles in both the Rebel Stakes and the Santa Anita Derby. I expect to see him in a close battle again.

Will Secretariat‘s Record Winning Time Be Broken? No (-7500)

There is a reason this prop is set at -7500. It is not going to happen. There have been a lot of unbelievable, once in a generation horses since Secretariat, and none have touched his time of 1:59.40. This is not the year it is going to happen.

Will There Be a Wire-to-Wire Winner? No (-1000)

With Omaha Beach scratched, the speed in this race is really just Maximum Security. I expect him to be on the lead early and fade as the field turns for home. I will lay the juice and say there is no wire-to-wire winner this Saturday.

What Post Position Will The Winner Come From? 16-20 (+130)

This bet gives you both Game Winner (#16) and Roadster (#17) which are two of the top three choices and you’re still getting plus money. This is easily the best value among these bets.