Kentucky Derby Bets Gone Astray

Most of us betting the Kentucky Derby are going to get it wrong…and as it happens everyday in horse racing, the losers will pay the winners. No doubt there will be a handful of big winners amplified through the megaphone of social media. If you’re one of the lucky few, I tip my Derby hat to you in advance. For the rest of us, allow me to provide your coulda, woulda, shoulda hindsight ahead of time, so just maybe your Derby bets won’t go astray. 

Here’s a brief list of mistakes you’re likely to make betting Derby 143...

You fell in love with a horse earlier in the year, or as a juvenile

Falling in love with an equine athlete is a fan’s perspective, while betting is a gambling affair. Hey, you saw talent early on in a precocious two-year, congratulations. Many times this means little to nothing for your Derby bets. Instead of sticking with a horse you scored with the first Saturday in January, it’s better to understand who’s improving in time for a peak performance on the First Saturday in May. Love hurts, but it hurts more when the blinders of fandom keep you from jumping off something that used to be a good thing. 

Sorry, move on before it’s too late - like you've never heard that before.

You suffered from information overload

Too much of anything is not a good thing. Tuning into every bit of pre-Kentucky information – from the backside to daily racing chat boards and everything in between, will simply confuse you. After you tune into a popular radio show, re-watch Derby workouts for a third time, create a spreadsheet comparing final 1/16 of mile closing times for all prep races dating back to 1972, etc., etc., you’ll be left with over-whipped cream for brains. Instead of a developing a solid wagering strategy, you’ll be left second guessing yourself and allowing the most recent bit of information to override any possible, reasonable bets you could have made.

Close the door on the overload.

Your handicapping was better than your wagering strategy

How many times have you or your betting mates said, “I’m a great handicapper and a bad bettor.” Ugh. Creating a betting strategy is just as important as finding a Derby winner. Personally, I toss $400 on superfectas (seven friends and I, at $50 each), an Oaks-Woodford-Derby Pick 3 ($80 budget), Pick 4 ending with the Derby ($50 budget) and if I feel rock solid in my top Derby choice a $50 win ticket. If you don’t create a plan and budget, you’re going to have a lot of bettor’s remorse. 

As the blanket of roses is given out and interviews conducted, you’ll end up going through a stack of losing tickets muttering, “What was I thinking?” You weren’t, so think ahead. You won’t regret it.

You didn’t eliminate enough horses

While you may be high on one or two horses, first eliminate Derby hopefuls who have no shot to finish in the money. Starting with horses you can confidently toss from contention puts you in a better place to cash. Yeah, I know this strategy eliminated horses like Mine That Bird and Giacomo, who keyed mind-blowing scores, but the majority of the time it saves you from worrying about also-rans like Tom’s Ready, Trojan Nation, Oscar Nominated and Majesto. All four came nowhere near a top four finish just last year. Want to cover yourself, so you don’t miss a bomb, hit the ALL button in one of your vertical bets if you can afford it or play a few birthdays.

Start by eliminating horses with no shot, getting your betting combinations into a reasonable budget.

Somehow you have received inside information 

The recently departed gambler, writer and columnist Jay Cronley said it best, “Inside information only applies to one horse.” In this case there are 19 others, whose information you don’t have. Good luck with that.

Backsides are like church socials, barbershops and beauty parlors, so take the gossip with a grain of salt.

You weren’t prepared

I know you’re wondering, “Bada Bing, what the heck is the difference between analysis paralysis and being prepared?” Great question…that only you know the answer to. For me prepared means:

• Two read-throughs of past performances
  • first time deeply, taking my time about 2-3 hours
  • second time a quick once over looking to find nuggets I missed, 30-45 minutes
• Watching all Mike Welsch’s Clocker Reports. I liked his approach and appreciate his experience and eye. He’s not for everybody, but he’s a source I trust
• Checking with two betting buddies

That’s it. For you being prepared may mean a little bit more, a little bit less. Just do your homework, so you can pull the trigger without wondering if you left something out.

You failed to have a strong opinion prior to Saturday

There is a caveat to having a Kentucky Derby betting opinion prior to race day - be open to only certain kinds of information important to you. It could be a changing track condition (although forecasts look good of this writing), paddock and post parade appearances, possible track bias, betting patterns, overlays, etc. But if you wait until the singing of My Old Kentucky Home to finally have an unwavering opinion it’s too late.

Form your opinion to withstand the last minute BS, but be open for some limited, meaningful information.

Other that the obstacles listed above making a winning Kentucky Derby bet is fairly straightforward and easy.

You may be wondering, “Well how have you done on Derby Day Bing?” The answer is all right. I hit the two-day Pick 3 with 40-1 shot, Princess of Sylmar leading it off in 2013, and the superfecta with American Pharoah, which paid poorly, but paid. For win bets, Orb, Super Saver, Grindstone and Thunder Gulch have come through for me in the last 21 years. 

There’s also a bunch of near misses including not playing a Pick 4 ending with a Street Sense single that would have paid over $2K and having three of four in the superfecta a bunch of times. The mistakes of my plays include some or all of what have just imparted to you, so I’m still learning and hope you are too.

Good luck in whatever way you play Kentucky Derby 143!