2020 Kentucky Derby Prop Bets

2020 Kentucky Derby Logo Track

It took a bit longer than usual to arrive, but the 2020 Kentucky Derby will finally take place this coming Saturday. Bettors will be making their usually picks for win, place and show as they try to diagnose how the race will paly out. But you’ll also find many people focusing on the best prop bets for the 2020 Kentucky Derby.

Most horse racing fans are accustomed to the Kentucky Derby taking place on the first Saturday in May. The world had other ideas in 2020, needless to say, forcing the race to get postponed. Luckily, the waiting is over and the race for the best three-year-old thoroughbred horses in the nation is scheduled to take place this Saturday, September 5 at Churchill Downs in Lexington, Kentucky.

That means that the prep season for the race has been much longer than usual. It also caused the Derby to get pushed back in the order for the Triple Crown. Usually, it’s the first leg, but this year it will be the second race in the series, since the Belmont Stakes already took place back in June.

For those who like to use the traditional horse racing wagers, having a heavy favorite can be problematic, especially if you’re looking for value and that horse ends up winning. The only way you can make a lot of money on a small wager would be to hit one of the exotic bets, like the exacta, trifecta and superfecta. And that can be extremely difficult to do because the margin for error is so slim.

Best Sites for 2020 Kentucky Derby Prop Bets

Luckily, the 2020 Kentucky Derby is such a popular race that top horse racing betting websites are likely to offer you some excellent proposition wagers. There are many advantages that the prop bets possess that can appeal to horse racing bettors on the lookout for good value. And these are advantages that the traditional horse racing wagers can’t claim.

The 2020 Kentucky Derby Offers Great Prop Betting Opportunities

First of all, the prop bets feature fixed odds, meaning that your odds are locked in once you make the wager, regardless of what else happens leading up to the 2020 Kentucky Derby on Saturday. This is opposed to the pari-mutuel wagering system typically used in horse racing, where odds can change right up to the point of the race. Having the fixed-odds prop bets means that you can lock in your value at the level it was when you made the wager.

In addition, the prop bets can be applied to many different aspects of the race. That means that, if you wanted, you could avoid dealing with a heavy favorite. You can concentrate instead on some kind of bet that could offer you a solid payback in proportion to what you wagered.

With that in mind, we’re here to help you navigate it all with a guide to the best prop bets available for the 2020 Kentucky Derby. We’ll explain how then different prop wagers work and take a look at the odds being offered. And we’ll also take it a step further by giving you our picks for what we think the right play will be for each of those proposition wagers.

Prop Bets For 2020 Kentucky Derby

Margin of Victory

  • Dead heat (+3000)
  • Nose (+1000)
  • Head (+800)
  • Neck (+800)
  • ½ length to ¾ length (+375)
  • 1 length to 2 ¾ lengths (+200)
  • 3 lengths to 5 ¾ lengths (+225)
  • 6 lengths to 7 ¾ lengths (+650)
  • 8 lengths to 10 ¾ lengths (+725)
  • 11 lengths to 14 ¾ lengths (+1000)
  • 15 lengths or more (+1200)

Outlook: To understand exactly what this bet means, a length is approximately the length of the average length of a thoroughbred horse from front to back. Once you get inside a half-length, the margins shrink to a neck (small), a head (smaller) and a nose (smallest.) A dead heat occurs when two (or more) horses hit the finish line together and even a photo can’t separate them, meaning that they essentially tied for first.

To give you some perspective, Tiz the Law, who is expected to be the heavy betting favorite for the 2020 Kentucky Derby, has won his last four races all within the range of 3 to 5 ¾ lengths. As you can see above, that bet returns $225 for every $100 you bet.

You could try to get fancy for value here and look for a smaller margin, if you choose. That should be the direction you should go if you think that Tiz the Law is going to get upset somehow. But the best play seems to be that 3 to 5 ¾ length wager, where Tiz the Law has been living lately, which would return you double your money and then some.

Time of the Quarter Mile

  • Over 22.8 seconds (-120)
  • Under 22.8 seconds (-110)

Time to the Quarter Mile

  • Less than or equal to 23 seconds (+100)
  • Greater Than 23 seconds (+140)

Outlook: We’ve lumped these two bets together because they’re about the same thing, just using slightly different odds and figures. If you look at a horse racing program, you will see that the races are broken down into several segments. In the case of a race that’s 1 ¼ miles long, like the Kentucky Derby, the races are broken down into quarter-mile sections.

As you watch the race, you’ll see a figure show up on the screen notifying the quarter-mile time, and the track announcer will also make note of it. The general rule of thumb in a horse race is that a quarter-mile should be ticked off in about 12 seconds or so. But, in a race like the Derby, where there are so many horses and a lot of talent, you can generally expect a little faster than that.

Still, many of these horses are still getting used to the longer distance of 1 ¼ miles. As a result, it’s reasonable to expect a somewhat slower pace in the early going as the horses feel each other out. Perhaps the best play here is to thread the needle: Go over 22.8 seconds and under 23 seconds, which would win you both bets at once.

Time of The Half Mile

  • Over 46.8 seconds (-110)
  • Under 46.8 seconds (-120)

Outlook: We’re looking at a similar concept to the above wager with this one, only the time is clocked at a different distance. In the case of the Derby, by the time they reach the half-mile marker, they’ll already have taken on the first turn. That will naturally slow things down from the opening quarter, which is why the benchmarks here are proportionally higher.

If you take a look at some of the bigger prep races held leading up to the Derby, you’ll see that most of these races come in under the benchmark of 46.8 seconds. On top of that, the early forecast for Louisville on Saturday looks pretty good. Obviously, that can change between now and Saturday, but it seems a slim chance that a sloppy track will be slowing every down.

Especially with a big favorite like Tiz the Law in the picture, it seems likely that there will be one or two “rabbits” in the race, horses trying to go quickly on the front end and steal out to an insurmountable lead. In the long run, that strategy seems unlikely to work. But it does put the odds in favor or a half-mile fractional time under 46.8 seconds.

Winner Leads Wire to Wire

Outlook: It’s important to understand what this means. A wire-to-wire winner doesn’t have to be out in front every single step of the race. They just have to be in front for every measuring point of the race (quarter, half, three-quarters, etc.) to be considered a wire-to-wire Kentucky Derby champion.

Even with those standards, wire-to-wire winners are exceedingly rare in the annals of the Derby. It has only happened 22 times and hasn’t occurred since 2002, when War Emblem pulled off the feat. Yet Maximum Security did indeed lead wire to wire last year, only to have the win taken away by a disqualification.

If a wire-to-wire winner is going to happen this year, it will likely come from one of trainer Bob Baffert’s contingent. Both Thousand Words and Authentic have proven capable of taking a good field all the way on the front end. That said, such an outcome is a real long shot with an 18-horse field, especially considering that Tiz the Law likes coming from off the pace, which means that the dull minus-800 bet is probably the play.

If Training Winner Is First-Time Derby Winner

Of the 18 horses in the 2020 Kentucky Derby field, six have trainers that have won before. Those gentlemen (Barclay Tagg, John Shireffs, Bob Baffert, Bill Mott, and Todd Pletcher; Baffert has two entries) tend to have contenders each and every year in the race. As for Tagg, he’s trying to get his first Derby Win in 17 years, following up Funny Cide in 2003.

Even though they make up a small percentage of the field, these trainers have the lion’s share of the top choices in this year’s race. The top four choices belong to these trainers. You have to go a couple of fifth choices, each with 20 to 1 morning line odds, before you get to a trainer who hasn’t won the Derby before.

This is a bet where you might think the numbers on your side if you take the underdog, since two-thirds of the field would get you the win. But the odds are overwhelmingly on the side of those trainers who have won it before. And considering that Tagg trains the heavy favorite in Tiz the Law, you really can’t hope to find much value in this one.

Number of Words in the Name of the Winner

  • 1 (+700)
  • 2 (+600)
  • 3 (-155)

Outlook: This bet is pretty self-explanatory, even for horse racing betting novices. At the end of the race, take a look at the name of the winning horse. Count the words and compare them to the odds that are listed above.

The obvious reason why the 3-word option is the one to beat here is the presence of Tiz the Law. On the morning line, he comes in at 4-5, which means that the three-word option would deserve the most betting attention of any of the options. Even though there are only three other horses in the field with three words in their names, none of which have much of a chance according to the oddsmakers, Tiz the Law carries all boats here.

If you are going to try to knock off Tiz the Law, the 2-word play seems like the best choice. There are more horses with two-word names in the field than any other option, which gives you strength in numbers. On top of that, several of those horses, including King Guillermo, Thousand Words and Honor A.P., are considered the best sleeper horses.

Number of Horse That Finishes Last

There are 18 horses in the field for the 2020 Kentucky Derby, down from the 20 that usually enter. Each is assigned a saddle cloth based on the post position that they have. At the end of the race, look at the horse that finishes last and see what that saddle cloth number is, and you’ll understand this bet.

The best way to look at this bet is to try and see which horses have the longest odds and checking out what their number is. Looking at this field, nine horses in the 18-horse field have morning-line odds of 50-1, which are the longest odds on the board. Of those, six of them are odd-numbered, and three are even.

That doesn’t necessarily mean that one of these horses will finish last. There is always the possibility that a particular horse, maybe even one of the favorites, falters and that the jockey decides not to push him and lets him back out of the race. But if you want to go with the oddsmakers, you are probably better off taking the odd bet here, even at odds that are less than appetizing.

Age of the Winning Trainer

  • Over 51.5 Years Old (-1500)
  • Under 51.5 Years Old (+750)

This is another one where the presence of Tiz the Law really tips the scales in a certain way. Barclay Tagg, the trainer of Tiz the Law, is in the over category here. So too are all the trainers mentioned above as having previously won the Kentucky Derby.

In other words, most of the top choices at the best 2020 Kentucky Derby betting sites are trained by gentlemen who have been around the block and then some. If you’re looking at possibilities from the younger generation, you probably have to start with up-and-comers like Peter Eurton or Saffie Joseph. And if you look at the odds on their horses, you can see that they might have to wait a bit before they can capture the Derby crown.

There is a reason that the odds are so heavily-skewed to the veteran trainers in this one. You are really going to have to reach to find a scenario where one of the younger trainers does major damage in this year’s race. As a result, you should probably be prepared to bet a lot to win a little with this wager.

Age of the Winning Jockey

  • Over 40.5 Years Old (+300)
  • Under 40.5 Years Old (-500)

Whereas training a Derby winner usually requires a certain amount of experience, riding one is another story entirely. It’s not that unusual for a younger jockey to step up and immediately come up with a winning performance in the biggest race of them all. But that’s not the reason why the under on this bet is such a heavy favorite.

It all comes down to the fact that Manny Franco, who will be aboard Tiz the Law, fits into the under category here. Again, this horse is an odds-on favorite according to the morning line, and odds for favorites usually drop once the betting public steps in and gets involved. In other words, even if every other jockey in the race were in the over category, the under should be favored here.

As for which jockeys might be prepared to upset the apple cart in this particular wager, John Velazquez and Mike Smith immediately jump to the fore. They are on the second and third choices in the race and they actually bracket Franco and Tiz the Law in terms of post position. Here is one bet where I think the value is such that going with the underdog might be worth taking the chance.

Who Will the Winning Jockey Thank First After Race in Horseback Interview?

  • Owner (+300)
  • Trainer (+300)
  • Horse (+300)
  • Family (+300)
  • God (+300)
  • Other (+300)

Outlook: This is a fun wager and one that you really don’t have to do too much analysis to take on. Notice that all the bets are evenly parceled out at plus-300, meaning that you’re going to get decent value no matter which one you take. And you can make a case for any of the choices above.

For those who might not know what we’re talking about here, at the immediate conclusion of the race, NBC sends out a reporter on horseback to talk to the winning jockey. It’s one of those fascinating little traditions that makes the Kentucky Derby what it is. And it’s what you should be watching if you make this wager.

If you really wanted to take an analytical angle on it, thanking God is usually the fallback here. Yet the jockey, fresh off a legendary win, might feel particularly grateful to the horse that brought him home. That’s why you should probably go with the horse in this bet, but you really can’t go wrong no matter which direction you turn here.

Will Winning Trainer Cry in Interview After Race?

Again, this is a wager where you really are taking a bit of a shot in the dark. There is no way you can judge how someone might react in the moment after their horse comes up with what might be the defining win of their career. Why is it that the “no” angle is so much more of a favorite than the possibility that they will shed some tears when NBC comes calling?

Well, these trainers are mostly folks who have been around the business for quite a long time. They’ve been there, done that, and even if they’re winning the Kentucky Derby for the first time, they still have probably won other big races along the way. The chance that they’ll get hysterical on air is somewhat slim.

Barclay Tagg, the trainer of heavy favorite Tiz the Law, does have an interesting story in that he would be winning the race at an age when most trainers have retired. Not to mention the fact that he would be winning the race 17 years after the first time he achieved the feat with Funny Cide. Maybe the emotion of all that will get to him, but, more likely than not, this one stands in the “no” category.

Will Winning Horse Have Ever Won Previously at Churchill Downs?

Churchill Downs is the home of the Kentucky Derby, of course, but is also home to racing at different points throughout the year. A few of the horses in this race have won at Churchill before. But one who hasn’t is Tiz the Law, and that immediately pushes the odds in the “no” direction for this wager.

Ironically, the only loss that Tiz the Law has suffered came at Churchill Downs last year. Some contrarians are pointing to that fact as a reason to possibly go against him when picking horses. But that race was before Tiz the Law hit his stride and came on a sloppy track, which means that it might not be relevant to what happens Saturday.

In any case, most of the top competitors haven’t even raced at Churchill to this point in their careers, let alone come up with a win there. This actually seems like one of the easiest picks in the entire list of 2020 Kentucky Derby prop bets. You can take the -300 with confidence that you’ll get something in return, even if it’s not a lot in proportion to your wager.

Will Handle For 2020 Kentucky Derby Exceed Handle For 2019 Kentucky Derby?

If you’re new to the betting world, you might not be familiar with the term “handle.” Handle is just a fancy name for the amount of money being bet on the race. That includes not only money bet by those at Churchill Downs, but also by those all over the world at simulcast areas and off-track-betting sites.

In 2019, the handle for the Kentucky Derby came in over $165 million. That set a new record for the race and was a ten-percent increase from the previous year. Basically, the 2020 Kentucky Derby has a tough act to follow.

The main reason that it will have a hard time matching that number won’t have anything to do with audience restrictions at Churchill Downs. Instead, there might be a lack of awareness for this year’s Derby, considering the postponement has put it at a time of year where it doesn’t usually take place. As a result, the no bet should be the choice here, even though it isn’t the more valuable of the two.

Will One of NBC’s TV Hosts Hit Their Trifecta Bet?

It isn’t the easiest thing being a horse racing announcer on a broadcast like the Kentucky Derby. Not only do you have to report the action, but you’re also expected to give your picks of who you think will win. Broadcasters in other sports usually don’t have to deal with that, but it’s all part of the Derby and its close connection to the betting world.

First of all, there will be probably be around six or so broadcasters making their picks on Saturday afternoon. That narrows the chances that someone might nail a trifecta, which means they pick the winner, second-place and third-place finisher in the correct order. As anyone who has ever bet on horses can tell you, trifectas are notoriously tough to hit.

Still, these broadcasters have the advantage of a heavy favorite to put on top, which, if Tiz the Law does deliver on that promise, takes one of the variables out of the equation. And there is zero value in going with the “no” bet here. This is one Kentucky Derby prop bet where the underdog is the smart play.

Will the Winner Of The Kentucky Derby Be Wearing Blinkers?

Blinkers are a piece of equipment that can be added to horses to improve their performance. In some cases, it helps a horse keep more of a straight line during a race, which shortens the distance that it will ultimately run. Other horses might need blinkers to stay focused on the task at hand and not worry about their competitors, since the blinkers will restrict the horse’s peripheral vision.

Many legendary horses have won blinkers during their careers. Included among them are Triple Crown winners like Gallant Fox, Whirlaway and Count Fleet. Why, even the great Secretariat, generally considered the best thoroughbred of all time, wore blinkers.

The only problem here is that Tiz the Law does not race with blinkers. As a result, your odds are skewed in a big way toward paying off more for those with blinkers in this race. In fact, they are skewed so much, that you’re really better off taking a stab at hoping Tiz the Law struggles and that one of his blinkered foes can pull the upset.

Will Secretariat’s Record Kentucky Derby Winning Time Of 1:59.4 Be Broken?

Secretariat’s record time, set as he begun his Triple Crown run in 2003, is one of the longest-standing records for a big race in all of horse racing. Think about it: in the last 47 years, as breeding methods have become streamlined and track surfaces have improved, Secretariat’s mark still looms large. And lately, nobody has even come close to threatening it.

The last three years aren’t a good judge, since each of those Kentucky Derby conditions featured sloppy racing conditions. 2016 was the last time there was a fast track, when Nyqist won in 2:01.31. That’s nearly two seconds off the pace of Secretariat.

The last horse to even threaten the mark was Monarchos, who came with a half-second or so in 2001. Still, why would you want to make a 1 to 45 bet on the record standing? If you believe that Tiz the Law is a truly special competitor, why not take the 15 to 1 chance that he can somehow beat history and stand in the same league as the greatest race horse ever?


We hope that we’ve helped you out with this article as you prepare to make your 2020 Kentucky Derby prop bets. These wagers really bring a lot of fun to the betting process. And, if you take your time, do your research, and choose wisely, they can be quite lucrative as well.

Jim Beviglia

Jim Beviglia joined Gamblingsites.org as a staff writer in 2018, parlaying his years of freelance writing into contributions on a number of different topics. He handles the sport of horse racing for GamblingSites.org and the intersection between the worlds of cryptocurrency and online gambling in a weekly blog.
For his full-time job, Jim handles the television and track announcing duties at a h …

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