2021 Kentucky Derby: Betting Guide and Strategies for all Budgets

Chris Adams

The first Saturday in May presents a wonderful betting opportunity for horseplayers with so many people tuned in to watch the big race. The Kentucky Derby will represent one of the largest single race handles in the United States all year.

In a pari-mutuel sport like horse racing that means that there is more money to go around to the winners. Taking even a little bit of time to handicap the race and formulate an opinion will immediately separate you from the players who choose to throw $5 on the jockey in the pink silks or the horse with the funny name.

This guide is designed to give you a leg up on the competition.

Pace Makes the Race

Understanding the pace scenario of the race is important. Some horses like to run on the lead while others like to sit off in a stalking position. There are also instances where horses like to sit several lengths off the leaders. After conserving energy they will try to accelerate to pass horses late.

The following is a pace analysis of this year’s runners. These are merely projections based on races to this point. It is not unusual for horses to suddenly take a different tactic to avoid trouble or catch the other jockeys off guard. However, the better idea of pace a player can have, the more likely they are to cash a ticket.

Early Speed

Rock Your World is the most likely leader. Other horses that have run their best showing early speed are Helium, Soup and Sandwich, Medina Spirit, and Midnight Bourbon. Based on internal pace figures it appears that Rock Your World should be able to easily get out quicker than these other runners. This could lead to the rest of the early speeds hopelessly chasing in behind. When the other runners start coming they are likely to drop back in the stretch.

Stalkers

This will be the area where the most likely threats to Rock Your World are jockeying for position. Essential Quality, Known Agenda, Hot Rod Charlie, Super Stock, Dynamic One, Sainthood and King Fury all running in this tier of horses which will likely be no more than five lengths off the leader. They will hope for a pace just quick enough to soften up the frontrunners allowing them to pounce around the final turn.

Closers

The remaining runners will likely be more than five lengths off the lead in the early stages. The runners are hoping for blistering pace that allows them to sail past all rivals as they get leg-weary. This is possible as none of these horses have traveled this far before.

Final Kentucky Derby Analysis

With Caddo River out it feels like Rock Your World gets to dictate everything on the front end. If he runs his race the other true speed types are going to struggle to keep up and will stop badly before the finish.

I see two potential scenarios playing out when they turn for home. The first is that Rock Your World has rocked them all to sleep and gets home without knowing there was even another horse in the race. If one of the lesser speeds really tries him and forces him to fight upfront he could lose just enough starch to hold off the cavalry.

There seems to be a solid group of viable stalkers in the field. If Rock Your World goes too fast too hard early, it is very likely he misses the board completely.

As these stalkers go Essential Quality is the obvious choice and probably the most likely board hitter in the race, but I prefer the closing kick of Highly Motivated extending out to the classic distance.

Given the quality of the middle group I don’t see a lot of chaos in the top 2 spots, but there are always surprises underneath in the trifectas and superfectas. Early meet indicators are that speed is winning and placing, but closers are finding ways to get up for pieces late.

Kentucky Derby Picks

  • Most Likely Pace Setter: #15 Rock Your World
  • Most Likely to Hit The Board: #14 Essential Quality
  • Best Value Win Contender: Highly Motivated (Top Pick)
  • Other Win Contenders: Hot Rod Charlie
  • Live Longshots: O Besos, Mandaloun, Super Stock, and Midnight Bourbon

For AI-generated picks and handicapping tools, check out our friends at DailyHorsePicks.com.

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Kentucky Derby Betting Strategy

Before you place a dollar on the Derby, figure out what your preferred betting style is and craft your bets according to that style. This will ensure that you can enjoy your Derby day experience. No matter how big or small your budget is, this wagering guide has something for everyone.

The following wagers are a combination of handicapping opinion and value estimation. With so many factors in horse racing it is hardly worth the risk to bet $20 to win $22.50. These wagers are designed to ensure that if they hit, the payout will be worth the risk.

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Understanding the Wager Types

For those new to betting on horse racing, you may find it helpful to first become familiar with the various types of bets that will be outlined in this article. The wagers provided here will focus on the Double, Win, Place, Show, Exacta, Trifecta, and Superfecta.

Before placing a bet always make sure you fully understand what is on your ticket and what needs to happen in order to win the bet.

For example, a 1/2/3 Trifecta means your horses must finish in that order. On the other hand, a 1,2,3 Trifecta Box means they can finish in any order. This is more likely to hit but is more expensive because you have to buy every possible combination.

If you’re not sure what your ticket means, it is usually best to cancel it.

Kentucky Oaks/Derby Double

While most will have their sights set on the Kentucky Derby, players can place bets before Friday’s Kentucky Oaks on the Oaks/Derby Double which requires you to have the top finisher in the Kentucky Oaks on Friday and the Kentucky Derby on Saturday.

For the following wagers the word “with” will separate Oaks horses from Derby runners.

The total cost of each wager is listed in parentheses at the end of the bet. Total cost represents all combinations within the bet.

$20 Bankroll:

  • $10 Double #10 Malathaat with #15 Rock Your World ($10)
  • $4 Double #10 Malathaat with #17 Highly Motivated ($4)
  • $2 Double #5 Pass the Champagne with #15 Rock Your World, #17 Highly Motivated, and #14 Essential Quality ($6)

$100 Bankroll:

  • $40 Double #10 Malathaat with #15 Rock Your World ($40)
  • $20 Double #10 Malathaat with #17 Highly Motivated ($20)
  • $5 Double #10 Malathaat with #6 O Besos, #18 Super Stock, and #7 Mandaloun ($15)
  • $5 Double #5 Pass the Champagne with #6 O Besos, #9 Hot Rod Charlie, #14 Essential Quality, #15 Rock Your World, and #17 Highly Motivated($25)

Kentucky Derby Single Race Wagers

The following wagers can be placed at any time prior to the Kentucky Derby. It is usually best to wait until after scratches have come out to make sure there are no late changes to your bets.

The following bets are broken down by budget and risk tolerance. It is important to remember that even conservative wagers are far from sure things. In general, the premise is that the conservative bets focus on maximum coverage of likely outcomes to increase the probability of having a winner that pays more than what you put in.

Aggressive bets are focused on making a score that you will be telling your buddies about for the next decade of Derbies. While these bets undoubtedly will have much higher payouts they are also predicated on significant chaos occurring and there is a much better chance of walking out with nothing but your memories of the Run for the Roses.

Moderate wagers fall somewhere in between with a bit of hedging on more likely outcomes with one or two chances to make a considerable score.

Betting Terminology

Some of the wagers below use the terms “Box”, “Key”, and “Wheel” which represent assigning multiple horses to a specific placing position.

The “Box”

The word “Box” means that the horses on your ticket can come in any order and you win. This is the most expensive and least efficient way to bet but can have its place in your Kentucky Derby betting strategy because of the liquidity in the pools.

The “Key” and “Wheel”

Keys and wheels are used to include multiple horses in different positions, without having to cover all possible combinations. These can be extremely helpful if you think you know the horse that will finish in a certain spot (key) or if you think a horse has little chance to hit one of the positions in the wager.

Wheels are best when you think a horse has a chance to win wire to wire or will completely fall apart and miss the board completely. Unlike the box which would require you to buy tickets with this horse in every spot, you can wheel them in the top spot and leave them off the rest of the ticket.

With wheels and keys the word “over” is used to separate between placing positions.

Example: Trifecta Key #1 over #2 and #3 over #2,#3, and #4

  • #1 must be in first
  • #2 or #3 must finish second
  • #2,#3, or #4 must finish third

$20 Bankroll

Conservative Approach

  • $10 Place #14 Essential Quality ($10)
  • $2 Exacta Box #14 Essential Quality and #17 Highly Motivated ($4)
  • $2 Exacta Box #15 Rock Your World and #17 Highly Motivated ($4)
  • $1 Exacta Box #9 Hot Rod Charlie and #17 Highly Motivated ($2)

Moderate Approach

  • $5 Exacta Key #15 Rock Your World over #9 Hot Rod Charlie and #17 Highly Motivated ($10)
  • $2 Exacta Key #17 Highly Motivated over #9 Hot Rod Charlie and #14 Essential Quality ($4)
  • $1 Exacta Wheel #15 Rock Your World and #17 Highly Motivated over #6 O Besos, #7 Mandaloun, and #10 Midnight Bourbon ($6)

Aggressive Approach

  • $4 Exacta Key #17 Highly Motivated over #6 O Besos, #7Mandaloun, #9 Hot Rod Charlie, #10 Midnight Bourbon, and #18 Super Stock, ($20)

$100 Bankroll

Conservative Approach

  • $50 Place on #14 Essential Quality ($50)
  • $1 Trifecta Wheel #14 Essential Quality, #15 Rock Your World, and #17 Highly Motivated over #14 Essential Quality and #17 Highly Motivated over #5 Sainthood, #6 O Besos, #7 Mandaloun, #8 Medina Spirit, #9 Hot Rod Charlie, #10 Midnight Bourbon, #11 Dynamic One, #14 Essential Quality, #16 King Fury, #17 Highly Motivated, and #18 Super Stock ($38)
  • $4 Exacta Key #15 Rock Your World over #6 O Besos, #7 Mandaloun, and #17 Highly Motivated ($12)

Moderate Approach

  • $10 Exacta Key #15 Rock Your World over #9 Hot Rod Charlie and #17 Highly Motivated ($20)
  • $6 Exacta Wheel #9 Hot Rod Charlie and #17 Highly Motivated over #14 Essential Quality ($12)
  • $2 Trifecta Wheel #15 Rock Your World and #17 Highly Motivated over and #9 Hot Rod Charlie, #14 Essential Quality, and #17 Highly Motivated over #6 O Besos, #7 Mandaloun, #8 Medina Spirit, #10 Midnight Bourbon, and #18 Super Stock ($50)
  • $1 Trifecta Key #17 Highly Motivated over #5 Sainthood, #6 O Besos, #7 Mandaloun, #8 Medina Spirit, #9 Hot Rod Charlie, #10 Midnight Bourbon, #11 Dynamic One, #16 King Fury, and #18 Super Stock over #14 Essential Quality and #15 Rock Your World ($18)

Aggressive Approach

  • $10 Exacta Key #17 Highly Motivated over #9 Hot Rod Charlie and #14 Essential Quality ($20)
  • $2 Trifecta Key #17 Highly Motivated over #9 Hot Rod Charlie and #14 Essential Quality over #5 Sainthood, #6 O Besos, #7 Mandaloun, #9 Hot Rod Charlie, #10 Midnight Bourbon, #11 Dynamic One, #14 Essential Quality, #16 King Fury, and #18 Super Stock ($32)
  • $1 Superfecta Wheel #10 Midnight Bourbon, #15 Rock Your World, and #17 Highly Motivated over #14 Essential Quality and #17 Highly Motivated over #6 O Besos, #10 Midnight Bourbon, #14 Essential Quality, and #17 Highly Motivated, over #6 O Besos, #7 Mandaloun, #8 Medina Spirit, #10 Midnight Bourbon, and #18 Super Stock ($48)

Good luck on all of your Kentucky Derby Wagers!

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