Anyone who has ever played the trifecta or superfecta in the Kentucky Derby knows that finding live longshots is the key to hitting those bets. With two exceptions, every Kentucky Derby since 2001 has seen at least one horse at odds of 20-1 or higher finish in the top four, and having more than one huge longshot hit the board has not been uncommon.

As a result, it can pay to think outside the box when handicapping the Derby in an effort to uncover live longshots capable of finishing in the top four. Finding the right ones isn’t easy — they’re longshots for a reason —but it’s always a fun and challenging task that can pay off in a big way if you’re right.

Below are three longshots that I feel have a chance to hit the board in the 2016 Kentucky Derby:

Majesto

Although Majesto lost the first four starts of his career, he ran very well in three of those races while holding his own against proven stakes horses like Destin and Gettysburg. He finally broke his maiden in his fifth start, defeating next-out maiden winners Dig Deep and Street Gray (Dig Deep also won a stakes race last week). Off that promising effort, Majesto was entered in the Florida Derby, where finished a second behind the unbeaten champion Nyquist.

Majesto’s Florida Derby effort was particularly noteworthy because while he did save ground throughout the race, he did so while racing over by far the wettest part of the track. Rain throughout the afternoon had left large puddles along the rail at Gulfstream Park, but Majesto showed no hesitation sloshing through them, and he stayed on gamely in the homestretch to finish just 3 ¼ lengths behind Nyquist.

To me, Majesto looks like a rapidly improving colt who is heading into the Kentucky Derby in great shape. He’s already proved that he doesn’t mind racing inside of horses, a good asset in the Derby, and his pedigree — by Tiznow out of the Unaccounted For mare Unacloud, the dam of 2013 Arkansas Derby winner Overanalyze — suggests that Majesto will have no trouble with the distance of the Derby. It’s also worth noting that Majesto has already run three races at nine furlongs, which is rare to see in a Derby contender. He may not win the Kentucky Derby, but I think Majesto has a strong chance to finish in the superfecta at around 30-1.

Suddenbreakingnews

Suddenbreakingnews prepares for the Kentucky Derby at Churchill Downs. (Eclipse Sportswire)

After winning the Grade 3 Southwest Stakes by 2 ¾ lengths with a visually spectacular late rally, Suddenbreakingnews had slightly troubled trips in the Grade 2 Rebel Stakes and Grade 1 Arkansas Derby, having to wait behind horses in the former race and having to rally very wide in the latter. But with the exception of the Rebel Stakes, he’s never finished worse than second in any of his races and has adapted to a wide variety of pace scenarios.

In terms of pedigree, he’s by Mineshaft, the sire of 2010 Derby runner-up Ice Box, and is out of a mare by Belmont Stakes winner Afleet Alex, who finished third in the 2005 Derby and sired the 2010 Travers Stakes winner Afleet Express. He seems to make his move in the homestretch as opposed to the far turn, so the long homestretch at Churchill should be to his liking. If the Derby pace is fast, expect to see him gobbling up ground in the final furlong to contend for a spot in the superfecta.

My Man Sam

He had a somewhat difficult trip in the Toyota Blue Grass Stakes, getting a very wide trip after starting from post 14, and despite rallying extremely wide at the top of the stretch, he finished strongly in the final quarter-mile to finish second, beaten just 1 ¾ lengths by winner Brody’s Cause. As a deep closer — as opposed to just a closer — My Man Sam hasn’t really shown any early speed at all, and much like Suddenbreakingnews, he does his best running in the homestretch rather than on the far turn. But he’s already achieved a lot for a horse with just four starts under his belt, and one more step forward could put him in the hunt for finishing in the superfecta.

Now it’s your turn! Which longshots do you like in the Kentucky Derby?