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Looking for a Kentucky Derby payday? Here are 5 long shots you can’t ignore.

A more sure bet is that one of this year’s lesser-touted contenders will end up factoring into the exotic wagering.
Kentucky Derby entrant O Besos is led onto the track at Churchill Downs Wednesday, April 28 in Louisville, Ky. The 147th running of the Kentucky Derby is scheduled for Saturday, May 1.
Kentucky Derby entrant O Besos is led onto the track at Churchill Downs Wednesday, April 28 in Louisville, Ky. The 147th running of the Kentucky Derby is scheduled for Saturday, May 1. [ CHARLIE RIEDEL | AP ]
Published Apr. 29
Updated Apr. 29

This year’s Kentucky Derby features a deserving favorite in Essential Quality and a handful of talented and proven 3-year-olds that’ll be nipping at his heels with relatively short odds.

But what about the long shots?

The Derby winner’s circle has, for the most part, been dominated by favorites in recent years. The top betting choice won all six Derbies from 2013 to 2018, and Authentic won last year’s race as the third choice in the field.

But longer shots have had their own success.

Related: Heading to the stretch with horse racing’s longest-tenured announcer

Country House — at odds of 65-1 — was declared the Derby winner via disqualification two years ago, the second biggest long shot to win in the race’s history. It wasn’t too long ago that Mine That Bird and Giacomo won at odds of 50-1.

Perhaps another 3-year-old with a big number next to his name on the Churchill Downs tote board will make his way to the winner’s circle Saturday?

That, as the odds would indicate, is a long shot.

A more sure bet is that one of this year’s lesser-touted contenders will end up factoring into the exotic wagering. And picking the right long shot to include in your exacta, trifecta and superfecta bets can lead to a nice payday, even if Essential Quality or one of the other favorites wins the race.

Five of the last eight Derbies have had a top-three finisher with odds of 30-1 or longer. The payout on a $1 trifecta bet in those five races ranged from $1,300 to $11,475. Ten of the past 13 Derbies have resulted in trifecta payouts of more than $1,000 on a $1 ticket, even with favorites winning most of those years and other top betting choices running in the money.

Sneaking a long shot into the superfecta can also pay off big time, obviously. In last year’s Derby, the top three betting choices — Authentic, Tiz the Law and Honor A. P. — all finished in the top four. They were joined by third-place finisher Mr. Big News, a 46-1 shot. A $1 superfecta ticket paid $7,925. The year before that, when Country House won, 14-1 shot Code of Honor finished second, and race favorites Tacitus and Improbable were third and fourth, the $1 superfecta payout was more than $51,000.

So, if you’re betting the Derby on Saturday, take a little chance and throw in a long shot.

Which one (or two, or three) to choose?

Here are five Derby contenders with morning-line odds of 20-1 or longer to keep an eye on.

6. O BESOS (20-1)

While other trainers waffled after their horses failed to finish in the top two of their respective final preps, Greg Foley made it immediately clear that O Besos would be set for the Derby starting gate if he had enough qualifying points to make the race. Following several defections, O Besos — the third-place finisher in the Louisiana Derby — was safely in, and he’s one of the most intriguing long shots Saturday.

Deploying a closer’s style, O Besos should be running in the stretch, and pinpointing a long shot that could be passing up tiring horses at the end is one of the best ways of finding value in your exotic betting tickets. O Besos’ sire, Orb, won the Derby in 2013 using a similar style. He was 18 ¾ lengths behind the leaders at the half-mile point — the fourth largest such margin on record for a Derby champ — and still managed to win by 2 ½ lengths.

O Besos doesn’t have the credentials that his daddy did — Orb was the Derby favorite, after all — but Foley’s colt has improved his speed numbers over every one of his previous starts, managed to close well in a Louisiana Derby with relatively soft pace numbers, and his running style should be beneficial Saturday as a possible hit-the-board long shot.

10. MIDNIGHT BOURBON (20-1)

It was a bit of a surprise to see Midnight Bourbon in the “20-1 and longer” crowd on the morning line Tuesday. This has been one incredibly consistent colt in 2021, which started with a win in the Lecomte Stakes, followed by a third-place finish (beaten less than 2 lengths) in the Risen Star Stakes and then a game second-place showing to Hot Rod Charlie in the Louisiana Derby.

Hall of Fame trainer Steve Asmussen is 0-for-21 with his Derby horses — most starts ever without a victory — but he’s had some tough luck on Derby Day, and he has finished second twice and third twice, including a runner-up showing with 33-1 shot Lookin At Lee four years ago. Midnight Bourbon has consistently high speed figures — only four Derby horses had a better Beyer last time out than his 96 in the Louisiana Derby — and the son of Tiznow should like the added distance Saturday.

Asmussen called getting the 10 spot an “ideal draw” Tuesday morning, and Midnight Bourbon will get a boost Saturday with the addition of Hall of Fame jockey Mike Smith, a two-time Derby winner who replaces Joe Talamo in the saddle. Midnight Bourbon should be near the leaders from the opening stages of the race.

“I think the 10 draw is perfect to establish the tempo that Mike wants,” Asmussen said.

13. HIDDEN STASH (50-1)

This 3-year-old colt has been a bit of a buzz horse all year, despite going winless in all three of his starts for 2021. Still, Hidden Stash — the first Derby horse from the BBN Racing syndicate — has an intriguing case to be a long-shot play Saturday.

The son of star stallion Constitution — a top sire for longer distances — has Smart Strike as a damsire and appears to be impeccably bred for the Derby distance. His lack of victories might be more related to circumstance than overall talent. He finished third in the Sam F. Davis Stakes (beaten a little more than a length) and second in the Tampa Bay Derby (beaten less than a length), with both races run at 1 1/16 miles. In the latter, Hidden Stash ran off in the post parade and ended up going an extra quarter mile or so before the race even began. He finished fourth in the Blue Grass Stakes, a race with zero early pace to suit his closing style.

He’ll probably get plenty of pace to run at in the Derby, and his connections have been supremely confident regarding his potential as a longer-distance performer.

Once again, when trying to make a splash with a trifecta wager, looking for a long shot who might be running late and get a bit lucky is a good way to go. Hidden Stash might fit that bill.

16. KING FURY (20-1)

Another long shot who should be running late and carries the dreams of a confident trainer, King Fury came roaring through the stretch in the Lexington Stakes three weeks ago at Keeneland for a victory in his first race in more than four months. Lexington’s own Kenny McPeek declared in the winner’s circle that the colt would be headed to either the Derby (if he had enough points) or the Preakness Stakes (if he didn’t).

Somewhat surprisingly, King Fury does indeed have enough points for Saturday’s race. And he comes into the Derby off a victory that — according to the speed figures — stacks up quite well with the numbers many of the race favorites put up in their final preps. The son of two-time Horse of the Year Curlin should love the added Derby distance and appears to have a pretty versatile running style. He got an excellent ride from Louisville-based jockey Brian Hernandez Jr. in the Lexington Stakes.

If King Fury can take even a small step forward off that race — and, just as importantly, if he can get a relatively clean trip from the back of the pack — he could very well factor into the Derby stretch run at a big price.

McPeek has had some good horses on Derby Day — including runner-up Tejano Run in 1995 and race favorite Harlan’s Holiday in 2002 — so it was worth noting when he said Tuesday that he’s “as confident as I’ve ever been” coming into this Derby with King Fury.

19. SOUP AND SANDWICH (30-1)

Trying to find a closing long shot who might be picking up the pieces late is one way to spice up a trifecta ticket. In case such a scenario doesn’t unfold, an alternative would be to pinpoint a front-running horse and hope he hangs around at the end. Florida Derby runner-up Soup and Sandwich is an interesting play in that regard.

Hall of Fame trainer Mark Casse brings the striking gray colt to Churchill Downs with few past results to go on. Soup and Sandwich didn’t make his debut until Jan. 28 and won his first two races by a combined 10 lengths before Casse entered him in the Florida Derby, where he set the early pace and eventually succumbed to Known Agenda in the stretch. Still, he held on for second in one of the biggest preps of the Derby season, and the performance came less than two months after his racing debut. That’s pretty impressive.

Soup and Sandwich also boasts an impressive pedigree. His sire is Into Mischief, the sire of Authentic, last year’s Derby winner and Horse of the Year. His damsire is the great Tapit (the father of Derby favorite Essential Quality).

A couple of the late defections from the Derby took some early speed out of the race. There will still be a battle at the front — Santa Anita Derby winner Rock Your World is among the top candidates to take the early lead — but if Soup and Sandwich can work his way into a relatively modest pace, it wouldn’t be a shock to see him in the mix down the stretch.

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