Looking for a big Kentucky Derby payday? These are the long shots you can’t ignore.

For the past decade, the Kentucky Derby has been dominated by horses with relatively short odds. When it comes to the winners, at least.

That doesn’t mean there hasn’t been money to be made on Derby Day.

All six winners from 2013 to 2018 were the betting favorites in the race, and then — following long-shot Country House’s controversial victory via disqualification in 2019 — the last two Derby win payoffs have also been pretty mild.

Odds are, another one of the top choices will cross the finish line first Saturday. But recent history also suggests that a long shot will end up on the board, and that’s where bettors can make a bundle with the right combination of horses.

Eleven of the last 14 Kentucky Derbys have resulted in a trifecta payout of more than $1,000 on a $1 ticket. And that’s because one or more of the long shots in the massive field often finds its way into the money on Derby Day.

Four of the last five Derbys have featured a horse with odds of 25-1 or longer in the top three, and — with so much money wagered across so many horses every year in the Derby — all it takes is one bomber to spice up a trifecta or superfecta ticket, even if race favorites occupy the other two or three spots.

Last year, Medina Spirit won the Derby at 12-1 odds — all bets were final before he was later DQ’d — with 26-1 Mandaloun in second and 5-1 horse Hot Rod Charlie in third. A $1 trifecta ticket paid $1,696. The year before that, the top three betting choices (Authentic, Tiz the Law and Honor A.P.) finished 1-2-3, but 46-1 shot Mr. Big News came in fourth, resulting in a $1 superfecta payout of $7,925.

And the story is similar in just about every other Derby in recent years.

So, when it comes time to make your wagers Saturday afternoon, it’s best to throw a long shot or three in your exotic bets.

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

5. Smile Happy (20-1)

Quite frankly, it was a pretty big surprise that Smile Happy was listed among the 20-1 shots on the morning line to start Derby week. Sure, he hasn’t won a race this year, but his resume includes a victory in the premier 2-year-old race at Churchill Downs in late November, and his two defeats in 2022 have come to Zandon and Epicenter, the two clear Derby favorites.

Though he was caught in the stretch by Zandon in the Blue Grass Stakes last month, there was no shame in his second-place finish there. In the Risen Star Stakes before that, Epicenter won from the lead, and Smile Happy deftly managed traffic in the stretch to finish second (a half-length ahead of Zandon, by the way) in his first race in nearly three months.

There are some distance concerns with the son of champion sprinter Runhappy, but 1 ¼ miles is new territory for everyone on Derby Day, and at 20-1 — or anything close to it — Smile Happy is worth consideration for a win bet Saturday. He’s certainly deserving of a long look with your trifecta and superfecta wagers, as well.

Corey Lanerie, who owns 19 meet titles at Churchill Downs and has been aboard for Smile Happy’s last three starts, is back in the saddle Saturday. This will be Lanerie’s sixth ride in the Derby and his best shot yet at a victory.

13. Simplification (20-1)

A third-place finish in the Florida Derby last time out has some souring on Simplification, but a longer look at that race and the ones that came before shows a horse that could hit the board at a big number Saturday.

The son of on-the-rise stallion Not This Time — same sire as Epicenter — won a stakes race on Jan. 1 and then jumped into the Derby prep season with a game effort in the Holy Bull Stakes, where he rallied from a terrible start to finish second behind White Abarrio.

Next time out, Simplification — with Jose Ortiz aboard for the first time — ran a huge race in the Fountain of Youth Stakes, winning that one by 3 ½ lengths and earning a 96 Beyer Speed Figure in the process. He finished third behind White Abarrio and the lightly raced Charge It in the Florida Derby after pressing the pace early, but that performance was better than it looked.

If he takes a step forward Saturday, he could very well be in the mix at the end.

14. Barber Road (30-1)

Part of the process of pinpointing long shots that might hit the Derby board is identifying those horses that are likely to be running at the end of the race, no matter what the circumstances. Especially in a grueling, crowded race like this one, plenty of contenders will bow out in the stretch (or even earlier) if the going gets too rough or demanding.

Barber Road probably won’t win Saturday, but he sure seems like one of the safest bets to run it out to the finish line. The son of Race Day is the most seasoned horse in the race with eight previous starts on dirt, and he’s 0-for-4 in 2022. But he’s finished first or second in six of his eight races, third in one and fourth in the other, his career debut last August.

He’s had to go wide around turns and fight through traffic, yet he always ends up near the front once the race is finished. Obviously, the company he’ll face Saturday is a considerable notch above what he’s seen on an Oaklawn Park prep circuit that hasn’t been well regarded this spring. Still, he’s liable to be passing plenty of tired horses in the stretch Saturday, possibly enough to hit the board as one of the longest shots in the field.

Barber Road’s last victory came at Churchill Downs, and while he’s only run once on an off track — a second-place finish at Oaklawn on a sloppy surface in January — he sure seems the type that would relish a rainy Derby Day.

16. Cyberknife (20-1)

Another surprise on the morning line Monday was Cyberknife, who was listed at 20-1 coming off a victory in the Arkansas Derby. The group that came out of those Oaklawn preps isn’t as highly touted as it has been in recent years, and the speed numbers that came out of the Arkansas Derby — including a 92 Beyer — are nothing special by the standards of this field.

All that said, Cyberknife — a son of champion Gun Runner — has been a highly regarded colt from the barn of Louisville native Brad Cox, who trained Kentucky Derby winner Mandaloun, 3-year-old champion Essential Quality, and Horse of the Year Knicks Go in 2021, winning the Eclipse Award himself for the second consecutive year.

Cyberknife has also been among the top performers in the mornings at Churchill Downs over the past few weeks, with Cox lauding his last two workouts as “the best Derby works I’ve seen” by any horse for this race. “I may be biased,” he added. “But that’s my opinion.”

In his very first Derby last year, Cox finished first and third with Mandaloun and Essential Quality. His overwhelming success over the past few years has him positioned as the hottest trainer in the country, and it would be foolish to dismiss what looks like his best horse in this race.

19. Zozos (20-1)

Speaking of Brad Cox, his lightly raced colt, Zozos, has the makeup of a potential star, and the Kentucky Derby could very well serve as his breakout moment.

The son of Munnings has just three career starts and didn’t run his first race until Jan. 23, but he kicked things off with two straight wins, the latter a 10-length romp that convinced his connections to take a shot at the Louisiana Derby.

In that race, Zozos set the early fractions and led into the stretch before being caught by Epicenter, who should vie for Kentucky Derby favorite status. Instead of giving in, however, Zozos stuck with it and kept running at Epicenter, making up some ground before the wire as the eventual winner geared down shortly before the finish line.

For such a lightly raced horse on a big stage, the final moments of that race showed a lot of moxie. The end result also included a 98 Beyer, which matches the best speed figure run so far by Zandon, the morning-line Derby favorite. (Only Epicenter, Messier and Taiba have done better in this Derby field).

Charge It is also a 20-1 shot with just three previous starts — and he’s been getting a ton of buzz in recent weeks — but, of those two, Zozos has the preferable running style for the Derby and has shown more maturity so far than Charge It, who was all over the place in the stretch of his Florida Derby runner-up finish last month.

If Zozos can avoid any blistering speed battles Saturday and run near the front at a reasonable pace, it’s fair to to think he’ll hang on pretty well in the stretch. Possibly well enough to finish in the money.

This story was originally published May 5, 2022 at 12:00 PM.

Ben Roberts

Lexington Herald-Leader

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Ben Roberts is the University of Kentucky men’s basketball beat writer for the Lexington Herald-Leader. He has previously specialized in UK basketball recruiting coverage and created and maintained the Next Cats blog. He is a Franklin County native and first joined the Herald-Leader in 2006. Support my work with a digital subscription