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Exotic wagers on the Kentucky Derby can pay off big. Here are the best bets.

Kentucky Derby entrant Game Winner is led off the track after a workout at Churchill Downs. (Charlie Riedel/Associated Press)

Updated to reflect the scratch of Haikal and jockey switch on Cutting Humor

Since the Kentucky Derby in 2013 adopted a points system to qualify for the 20-horse field, chalk has ruled the winner’s circle. Justify, Always Dreaming, Nyquist, American Pharoah, California Chrome and Orb were all post-time favorites, returning between $6.60 and $12.80 on a $2 win bet — a far cry from huge payouts of yore, which included I’ll Have Another ($32.60 in 2012), Animal Kingdom ($43.80 in 2011), Mine That Bird ($103.20 in 2009) and Giacomo ($102.60 in 2005).

Everything you need to know about the 2019 Kentucky Derby

On the other hand, exotic bets such as the trifecta (picking the first three finishers in order) and superfecta (picking the first four finishers in order) continue to provide betting bonanzas. Last year’s $1 superfecta paid $19,618.20. In 2017 the $1 triple paid $8,297.20 in addition to another monster superfecta ($75,974.50).

Kentucky Derby
$2 win bet paid
$2 exacta paid
$1 trifecta paid
$1 superfecta paid

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Those exotic bets should again offer the highest reward this Saturday. But first, we must narrow the candidates.

Isolating the top three or four finishers in a 20-horse field known for its chaos isn’t easy, but in addition to having a good pedigree and a solid foundation, a horse needs tactical speed to be able to keep up with the pace.

Competing horses Game Winner and Improbable galloped along the track on May 2, two days ahead of the Kentucky Derby in Louisville. (Video: AP)

Brisnet classified just one horse in the field, Omaha Beach, as a need-to-lead type, or 'E' horse, but he was scratched on Wednesday, leaving 15 horses set to be stalk the early pace (‘EP’ horses) or close to it ('P' horses) between the first (half-mile) and second (three-quarters of a mile) calls. Four others are considered sustainers or closers (’S') and will make their move from farther back.

2019 Kentucky Derby horses, post positions, odds, analysis and start time

Need-to-lead ('E')
Early presser (‘EP’)
Presser ('P')
Sustainer or closer ('S')
Maximum Security
Win Win Win
Cutting Humor
Code of Honor
By My Standards
Country House
Master Fencer
Gray Magician
War of Will
Long Range Toddy
Plus Que Parfait
Game Winner

However, Tuesday’s post position draw will force some horses out of their comfort zone. For example, Mark Casse, trainer of War of Will (post position No. 2) said after the draw that his horse will “probably be on the lead and play catch me if you can.” If he doesn’t go to the front, look for Tax, in post No. 3, to “come out running and sit on the rail,” according to Tax’s trainer, Danny Gargan. Maximum Security (No. 7) will also likely be up front early but, with a lack of true speedsters in the race, the pace shouldn’t be fast enough to hamper Maximum Security’s ability to last 1¼ miles.

Being among the first flight of horses is key. Over the past six years every Kentucky Derby winner but one, Orb in 2013, was classified as having a stalking (‘EP’) running style. Half of the horses (12 out of 24) that hit the board over that span had an ‘EP’ running style as well with seven others listed as pressers ('P'), horses sitting just off the leaders at the first call.

Maximum Security qualifies on merit plus running style. I would also add Game Winner, Vekoma, Tax, Spinoff and Improbable as good value plays to hit the board on Saturday over a fast track.

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Improbable is listed by Brisnet as a presser but he’s never been more than 2½ lengths behind the leader at the first or second call. Nyquist was four lengths behind the leader at the first call in the 2016 Kentucky Derby and American Pharoah was two lengths off the lead at the first call in 2015. Both won and Improbable looks like a winner here, too. At the very least, he’s worth using as a key horse in your trifectas and superfectas.

Spinoff inherited almost three times as much speed as stamina from his lineage (2.78 Dosage Index) and his early presser running style should have him in prime position to make a splash.

Vekoma has a similar speed profile (2.56 Dosage Index) and his victory in the Blue Grass — which included a career high Brisnet pace figure (how fast he ran from the start to the second call) of 114 — is reason for optimism this Saturday.

Game Winner failed as the favorite in his last two races but he has hit the board in all six of his starts, never finishing worse than second. But Baffert has trained two Triple Crown winners in the past three years so you can never count one of his horses out.

Tax might have to expend energy to get a comfortable spot on the rail but he has three triple-digit Brisnet speed figures in a row with a new career pace figure (105) in his last prep, the Wood Memorial at Aqueduct, making him an attractive overlay for the superfecta at 20-1 odds.

Win Win Win, By My Standards and Cutting Humor also deserve consideration in superfecta wagers.

Win Win Win closed into a fast pace during his second-place finish in the Blue Grass in April and his pedigree sets up nicely for a sustained run at the classic distance.

By My Standards set a career-high Brisnet speed figure in his Louisiana Derby win (102) and his trainer has a positive expectation for graded stakes races in 2019, meaning a $2 blind wager on Bret Calhoun’s horses in these events would net you a 74-cent profit this year. Same for jockey Gabriel Saez (plus-$1.18 net profit on route races per $2 wagered in 2019), who has ridden this horse since his first career start at Churchill Downs in November of last year.

Mike Smith, Hall of Fame jockey and two-time winner of the Kentucky Derby, will replace Corey Lanerie on Cutting Humor. The dark brown colt should in touch with the leaders early, similar to his victory in the Sunland Derby, allowing him to use his late kick to grab a piece of the board.

With that in mind, here is how I would construct my trifecta and superfecta tickets:

Trifecta betting strategy

5 with 14, 16 with 14, 16, 19

14, 16 with 5 with 14, 16, 19

14, 16 with 14, 16, 19 with 5

Superfecta betting strategy

5 with 14, 16 with 2, 14, 16, 19 with 2, 3, 6, 7, 10, 14, 16, 19

14 with 5 with 16, 19 with 2, 3, 7, 10, 14, 16, 19

16 with 14 with 5 with 2, 3, 6, 10

Correction: Superfecta payouts reflected 10-cent wagers instead of $1 wagers. This has been fixed.

Read more:

Here is the Bob Baffert horse that will win the Kentucky Derby

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Kentucky Derby post position trends: There’s magic in the middle