How to Win Big Betting the 2019 Kentucky Derby Favorite

Tips
Last year, Justify became the sixth consecutive favorite to win the Kentucky Derby, the longest streak in the race’s 144-year history. (Eclipse Sportswire)

When a favorite wins a particularly famous stakes two or three times in a row, it’s a trend.

When it happens four or five times in a row, you figure it’s time to bet against the streak.

When it happens six times in a row?

That’s the dilemma facing handicappers who are spending countless hours studying past performances for the Kentucky Derby Presented by Woodford Reserve. Do you just waive a white flag and back the favorite? Or do you figure that after six straight years, the Derby will finally revert to its old unpredictable self.

It has to, right?

Not necessarily.

For the all the talk of Saturday’s run for the roses being a wide-open race, the opening leg of the Triple Crown initially had a solid favorite in Omaha Beach who ended up being scratched due to an entrapped epiglottis on May 1. Now, favoritism will probably fall to one of three Bob Baffert-trained horses: Game Winner, Roadster, or Improbable. Each of them has a good chance to extend that six-year streak of winning favorites.

So, what’s a handicapper to do?

Let’s examine the options.

If you are traveling the longshot route, and you’re right, you will be rewarded, unless you fall victim to a brain freeze at the betting windows.

For starters, you should make some exotics bets keying your top selection. There’s surely nothing wrong with a five-horse exacta box in a 20-horse field, but give yourself a chance to not only feel good about picking the winner, but to make some serious cash, especially if he’s a longshot.

There are various ways to make that play, but don’t ignore a win bet to lock in some simple profit on a longshot, especially since there will be very little change in the odds during the final minutes before post time. It’s almost like Exchange wagering.

While some people believe the exotics are the way to go – and there’s no argument from me about that – for less seasoned players, there’s value in making at least one bet where you know what you will get for your bet as opposed to having to see who finishes second or third or wins a previous or upcoming race.

I’m reminded in this instance of an old turf writer/handicapper friend (swear it’s not me, even though I’m old) who spent the days leading up to the 2002 Belmont Stakes telling everyone that 70.25-1 longshot Sarava would win the race and thwart War Emblem’s Triple Crown bid. People thought he was crazy, until Sarava won. The story doesn’t end there, though. While he was sure Sarava would win, he was also certain that 16-1 shot Medaglia d’Oro would be up the track and put his bankroll into play betting exotics with Sarava on top and everybody but Medaglia d’Oro underneath in exactas and triples.

Needless to say, Medaglia d’Oro finished second and there was one rather upset turf writer who loved a horse that paid $142.50 to win and topped a $2,454 exacta and a $25,209 trifecta and somehow managed to lose his shirt on the race.

Now, if you are going to bet the favorite, the win bet is a lesser option. Maybe you can use it to cover your bets, but for the most part, even a favorite in the Derby can return a bundle of cash in the exotics due to 19 other horses bringing money into the wagering pools.

California Chrome in 2014. (Eclipse Sportswire)

In a sense, the best path remains playing doubles, Pick 3s and Pick 4s leading into the Derby. This way you will know if you’re alive and what your ticket/tickets will be worth heading into the Run for the Roses. This way you can hedge your bets and give yourself more options to break even or make money.

And don’t worry, you can turn a nice profit on those bets, even with a favorite anchoring the sequence.

Let’s look back at last year when eventual Triple Crown winner Justify made it a six-pack of favorites and paid $7.80 to win. The $2 exacta with Good Magic returned $69.60. Not bad at all for a favorite and the previous year’s 2-year-old champion. The $2 trifecta, with Audible added to the mix, returned $282.80, again not bad for tossing in the Florida Derby winner and playing three of the top six betting choices.

Now, if you like Omaha Beach and believe longshots will follow him under the wire, the vertical wagers are a definite option. A good example of that was 2014 when California Chrome won at 5-2 but Commanding Curve was second at 37.80-1 and 8.70-1 third choice Danza was third. The exacta paid a very robust $340 and the trifecta $3,424.60, both for a $2 wager.

Last year, however, the real boost to the Derby payoffs came from the races before it as the Pick 3 also featured Funny Duck ($81.40) and Yoshida ($21.90). Now if you are a fan of, let’s see, “Disco Duck” and trainers Bill Mott and Bob Baffert, all you needed was a few bucks to collect a $2 Pick 3 worth $13,098.20.

You do have to wonder if Margaret Reid liked “Disco Duck” or Donald Duck, because she somehow only needed an $18 wager to collect $1.2 million from a $1 Pick 5 wager that closed up shop in the Derby. So, yes, miracles happen.

Yet for most of us, if you singled Justify, it might have required a 10 x 6 x 1 bet to cover the needed bases on the odds board. That’s $120 invested (on $2 bets) for a $13,098.20 Pick 3 return, which beats the $468 you would have pocketed for a $120 win bet on Justify.

The previous two years the $2 Pick 3 paid much less, though $906 and $830 are nice prices for sequences that ended with a favorite and could have been bet akin to a double with a last-race single.

Thanks to Yoshida, last year's $2 double returned $88.20. Putting the same $120 into play with six double combinations, the return would have been $882.00. That’s not as good as $13,098.20, but it’s still a nice piece of profit.

Also keep in mind there are doubles and a Pick 3 after the Derby, which could bail you out. These two final races on the card are allowance and maiden races, which usually turn out to be chalky or produce very logical winners.  

In the double linking the Derby and the 13th race last year, Justify teamed with 3.10-1 second choice King Zachary ($8.20). The $2 double came back $40.20, which could have been covered for a 1 x 2 wager for $4.

In the last race, 3.20-1 second choice Limation prevailed ($8.40). That meant a 2 x 2 x 2 Pick 3 ticket worth $16 covering the top two choices in each race would have returned $210.20 for $2 – and an $8 bet (1 x 2 x 2) also would have sufficed.

So on Saturday, if the Derby is approaching and you’re having a bad day at the windows, don’t give up. John Wayne and the cavalry may be on the way to save you. The Derby is definitely a one-of-a-kind race and a one-of-a-kind betting opportunity, even if you like the favorite.

2019 Kentucky Derby presented by Woodford Reserve
May 4th, 2019

Winning Time: 2:03.93
  • Purse: $3,000,000
  • Distance: 1 1/4 Miles
  • Age: 3 yo
  • Surface: Dirt
  • Winning Time: 2:03.93
Results
Win
Place
Show
1st
20 Country House
$132.40
$56.60
$24.60
2nd
13 Code of Honor
$15.20
$9.80
3rd
8 Tacitus
$5.60
4th
5 Improbable
5th
16 Game Winner
6th
15 Master Fencer (JPN)
7th
1 War of Will
  • Owner / Gary Barber
  • Breeder / Flaxman Holdings Limited
8th
9 Plus Que Parfait
9th
14 Win Win Win
10th
10 Cutting Humor
11th
3 By My Standards
12th
6 Vekoma
13th
21 Bodexpress
14th
2 Tax
15th
17 Roadster
16th
18 Long Range Toddy
17th
7 Maximum Security
18th
19 Spinoff
Scratches
Payoff
Pick 3
7-12-20
7-12-20
$639
Pick 3
OAKS/FRSTR/DERBY 13-12-20
OAKS/FRSTR/DERBY 13-12-20
$2,073
Pick 4
3-7-12-20
3-7-12-20
$11,326
Pick 5
2/8-3-7-12-20
2/8-3-7-12-20
$72,318
Pick 6
OAKS/DERBY P6 1-13-3-8-12-20
OAKS/DERBY P6 1-13-3-8-12-20
$67,936
Pick 6 Jackpot
4-2/8-3-7-12-20
4-2/8-3-7-12-20
$271,870
Daily Double
OAKS/DERBY 13-20
OAKS/DERBY 13-20
$1,291
Daily Double
12-20
12-20
$121
Exacta
20-13
20-13
$3,010
Future Wager
SIRE WAGER - 24
SIRE WAGER - 24
$14
Future Wager
SIRE EXACTA 24-17
SIRE EXACTA 24-17
$89
Future Wager
EXACTA POOL 3 - 4-3
EXACTA POOL 3 - 4-3
$1,089
Future Wager
EXACTA POOL 1 - 24-2
EXACTA POOL 1 - 24-2
$109
Future Wager
POOL 4 - 24
POOL 4 - 24
$40
Future Wager
POOL 1 - 24
POOL 1 - 24
$5
Future Wager
EXACTA POOL 4 - 24-5
EXACTA POOL 4 - 24-5
$793
Future Wager
EXACTA POOL 2 - 24-18
EXACTA POOL 2 - 24-18
$551
Future Wager
POOL 3 - 4
POOL 3 - 4
$61
Future Wager
POOL 2 - 24
POOL 2 - 24
$8
Superfecta
20-13-8-5
20-13-8-5
$51,400
Super High Five
20-13-8-5-16
20-13-8-5-16
$544,186
Trifecta
20-13-8
20-13-8
$5,738
Race Replay
Play
Payoff
Pick 3
7-12-20
7-12-20
$639
Pick 3
OAKS/FRSTR/DERBY 13-12-20
OAKS/FRSTR/DERBY 13-12-20
$2,073
Pick 4
3-7-12-20
3-7-12-20
$11,326
Pick 5
2/8-3-7-12-20
2/8-3-7-12-20
$72,318
Pick 6
OAKS/DERBY P6 1-13-3-8-12-20
OAKS/DERBY P6 1-13-3-8-12-20
$67,936
Pick 6 Jackpot
4-2/8-3-7-12-20
4-2/8-3-7-12-20
$271,870
Daily Double
OAKS/DERBY 13-20
OAKS/DERBY 13-20
$1,291
Daily Double
12-20
12-20
$121
Exacta
20-13
20-13
$3,010
Future Wager
SIRE WAGER - 24
SIRE WAGER - 24
$14
Future Wager
SIRE EXACTA 24-17
SIRE EXACTA 24-17
$89
Future Wager
EXACTA POOL 3 - 4-3
EXACTA POOL 3 - 4-3
$1,089
Future Wager
EXACTA POOL 1 - 24-2
EXACTA POOL 1 - 24-2
$109
Future Wager
POOL 4 - 24
POOL 4 - 24
$40
Future Wager
POOL 1 - 24
POOL 1 - 24
$5
Future Wager
EXACTA POOL 4 - 24-5
EXACTA POOL 4 - 24-5
$793
Future Wager
EXACTA POOL 2 - 24-18
EXACTA POOL 2 - 24-18
$551
Future Wager
POOL 3 - 4
POOL 3 - 4
$61
Future Wager
POOL 2 - 24
POOL 2 - 24
$8
Superfecta
20-13-8-5
20-13-8-5
$51,400
Super High Five
20-13-8-5-16
20-13-8-5-16
$544,186
Trifecta
20-13-8
20-13-8
$5,738

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