Larry Martino

Larry Martino

Weekdays 3:00pm - 8:00pm

If you are not a horse racing aficionado, and you are looking for a fun way to bet on this year’s Kentucky Derby, then try this out.

There are usually 20 horses in the field for this classic horse race. That’s a lot of horses to fit on the track. All sorts of bumping goes on at the start of the race. The speed horses go to the front of the pack. The horses that prefer to charge down the stretch to catch the leaders as they come down to the wire hang back at the beginning of the race. There is a great deal of strategy utilized by each trainer, jockey, and horse.

But then sometimes, it all comes down to luck and which horse loves running on the track at Churchill Downs. Most of the horses are shipped in from other race tracks around the country. You just never know how the favorites will perform, or which of the long shots will shock the world. Since I don’t have time to handicap horses or races, I like to bet on the long shots. If you pick the winner, there is usually a big payout.

Now, I certainly do NOT guarantee that my method will work, or that you will win money. This is gambling. And, if you asked an expert handicapper, they would tell you to NEVER throw your money away on bets like the ones I am about to suggest. But I have hit some big paydays on Kentucky Derby day in the past by betting on long shots, and outside post positions. I’ve also lost a bunch of cash too. This year, I’m gonna bet $2 dollars to win on each long shot, post positions 10 through 20.

I did a little research for this article and found that since the year 2000, 13 Kentucky Derby winners have come from the outside, double-digit, post positions (10-20). They haven’t all been longshots, but it seems that although those outside positions mean the horses have to run a little further than the horses hugging the inside rail, they seem to have less traffic in front of them to navigate around. Last year’s winner, Rich Strike, came from post position #21 to win the Derby and paid $163.60 on a $2.00 dollar win wager!

Whether you choose to bet on the race or not, enjoy the most exciting two minutes in sports when watching the 2023 Kentucky Derby this Saturday, May 6th.

Scroll down to watch videos of some of my favorite long shot winners from those outside posts in past years from NBC Sports and

  • #21 "Rich Strike" Wins The 2022 Kentucky Derby

    OMG! Man, I wish I had made it to the sports book to bet on this one. I would have been bragging about it for weeks. Oh well, ya snooze, ya lose. The longest shot in the field, Rich Strike paid $163.60 for a $2 dollar wager to win. Exciting finish to that race too. Love those close calls at the end when a horse comes out of nowhere to win it.

  • #20 "Country House" Wins The 2019 Kentucky Derby

    Believe it or not, my wife had this winner. She lucked out because the horse which crossed the finish line first was eventually disqualified. We went out for steak dinners that night, thanks to Country House claiming the first leg in the 2019 Triple Crown. It was kind of an anti-climactic way to win though because we had to wait all that time for the official result.

  • #10 "Giacomo" Wins The 2005 Kentucky Derby

    Another thrilling finish to this Kentucky Derby, as Giacomo surges past the leaders to claim victory. At the time, this was the second-highest payout in Kentucky Derby history, returning $102.60 on a $2 dollar win wager. The biggest payout on one of those $2 win bets came way back in 1913 when Doneraile paid $184.90. Man, that was a lot of money back in those days. Last year’s Kentucky Derby winner, Rich Strike, now holds the second-highest winning payout in Kentucky Derby history behind Doneraile.

  • #16 "Monarchos" Wins The 2001 Kentucky Derby

    Monarchos ran this Derby almost as fast as the amazing Secretariat, who ran it in 1:59:40. Monarchos’ time was 1:59:97. Incredible. It was not a huge payout, but this horse was certainly not the favorite, paying $23 on a $2 dollar win wager. The second place finisher in the ’01 Derby, Invisible Ink, who also ran a very fast race, was an even bigger long shot, coming out of the #13 post position. Maybe we should be making place bets instead of win bets.

  • #19 "I'll Have Another" Wins The 2012 Kentucky Derby

    The 2012 Kentucky Derby winner went off at 15-1 odds, racing out of post position 19. I’ll Have Another was ridden by 25-year-old jockey Mario Gutierrez, who was making his first start in this prestigious race. He and his horse made a very dramatic late race surge to overtake the leaders and claim the first leg in the ’12 Triple Crown. A $2 win wager would have netted you $32.60 that year.

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