2019 Kentucky Derby Dark Horses and Longshots

The 2019 Kentucky Derby takes place on Saturday, May 4. As is almost always the case, 20 horses will enter the starting gate. Because so many three-year-olds run for Derby glory, it helps to handicap favorites and then handicap dark horses and longshots. Check out Kentucky Derby betting odds for dark horses and longshots to win on the first Saturday in May!

2019 Kentucky Derby Dark Horses and Longshots

  • When: Saturday, May 4 at 6:50pm ET
  • Where: Churchill Downs Racetrack
  • TV: NBC
  • Live StreamNBCsports.com

2019 Kentucky Derby Odds

  • War of Will +2000
  • Cutting Humor +2000
  • Win Win Win +2000
  • Plus Que Parfait +2000
  • Haikal +2000
  • By My Standards +2500
  • Tax +2500
  • Spinoff +2500
  • Long Range Toddy +3300
  • Gray Magician +3500
  • Country House +5000
  • Master Fencer +6600

War of Will

He owned the prep races in Louisiana until the big one, the Grade 2 Louisiana Derby. There’s a reason for the bad performance, though. War of Will lost action after getting hurt during the race. He’s been training lights out and Mark Casse is one of the best in the business. Still, he’s got to run much faster to win the Derby than he’s ever before run.

Cutting Humor

The Todd Pletcher trainee gets in due to his victory in the Sunland Derby. Sired by First Samurai, his owners purchased him for $400,000. There are some things to like, but he didn’t beat much in the Sunland Derby and could be a cut below these right now. Pletcher doesn’t often prep them in New Mexico. So we must question what he really thinks about this runner.

Win Win Win

He made a furious rally to get up for second in the Blue Grass Stakes. He wasn’t going to catch Vekoma even if he had started his rally earlier, though. He might be too far behind the front runners to win, but he could get up for third or fourth. So, use him in your exotics.

Plus Que Parfait

The UAE Derby has yet to produce a competitive Kentucky Derby horse, much less one that wins. Trainer Brendan Walsh decided to go for it in Dubai after watching War of Will put a beat down on Plus Que Parfait in both the Risen Star Stakes and the LeComte. Because he won in Dubai, Walsh will run him in the Derby even though he’d have to improve big time to have any say.


Heading into the Wood Memorial, the big question was whether Haikal’s closing kick could be as effective at 1 1/8 miles as it was at 1 mile. Because he couldn’t beat Tacitus or Tax even though he chased the same fast pace, the answer must be that his closing kick isn’t as effective at any distances longer than a mile.

By My Standards

Talk about a dark horse with a shot. By My Standards, a Goldencents sired runner trained by Bret Calhoun, broke his maiden on February 16. Then, he won the Louisiana Derby in his next race. He’s talented, no doubt, and a lot of times when they get good, they stay good. Pay attention to this guy on Derby Day.


He’s never run a bad race. Not only that, he might have held off Tacitus if jockey Junior Alvarado had kept him closer to the front runners. He’s bred to run all day. So, he won’t get tired in the stretch. There’s a lot to like about Tax. He’s another dark horse with a real shot at Derby glory.


Spinoff is trained by Todd Pletcher, just like Cutting Humor. That alone means we must take him seriously. He’s already the wise guy choice with at least one well-known horseplayer providing reasons to back him. He hung in the stretch and that’s the reason By My Standards beat him, but Spinoff is a talented colt that could surprise on Saturday. If you like him, bet him right now because you’re not going to get 20/1 on Derby Day.

Long Range Toddy

He beat Improbable by a nose in the Rebel Stakes, but then he failed miserably in the Arkansas Derby. He’ll be a good horse because he’s trained by Steve Asmussen. He probably won’t be good enough to win on May 4, though.

Gray Magician

Finishing second to Plus Que Parfait in the UAE Derby provided enough points for Gray Magician to get into the starting gate. It’s hard to see him having much of an impact. Peter Miller’s a good trainer, but the Kentucky Derby could be too much for him.

Country House

Tacitus’ trainer Bill Mott also saddles Country House. Although he ran well to finish third behind Omaha Beach and Improbable in the Arkansas Derby, he’d have to improve big time to hit the board on Saturday. It could happen. It’s almost impossible to see it happening.

Master Fencer

In Churchill Downs’ quest to get more international runners into the Kentucky Derby, they decided to give an invitation to Master Fencer’s connections. He does have some dirt breeding with Deputy Minister on the bottom, and he did win a 1 1/8 mile stakes, but the competition he’s faced in Japan is no where near as talented as what he faces on Saturday. The only reason we can’t say that he has no shot is because the Derby is a horse race, and anything is possible once the gates open.