How to Pick and Bet on a Kentucky Derby Winner

Although there are people more qualified to give Derby tips, like many financial commentators, I won’t let lack of expertise stop me.

Betting to show is a practice that I follow religiously. . (My mother was a sucker for horses with funny names.) I just follow the odds. If dad ever met the professors, he would have punched them in the nose. Betting to show fits with my overall philosophy about investing. I didn’t pick Sunday Silence because of my system. I go the track a few times a year and bet small amounts.

Dad liked the excitement of big odds and big payoffs.

It drove him absolutely crazy. I would bet $10 and win.

I picked the horse because of an alumni connection to a man I had never met.

It was written by two statistics professors and not the easiest book to read.

When your sitting back

In your rose pink Cadillac

Making bets on Kentucky Derby Day

– The Rolling Stones

He is the author of Son of a Son of a Gambler: Winners, Losers and What to Do When You When The Lottery.

My father, a professional gambler, absolutely HATED my betting system. He knew everything about the horse’s past performance, their breeding and who was riding them. He and I would go to Keeneland every session and we never picked the same horse.

I came to the conclusion that by living in Kentucky, I needed to know how to bet on horses. It was a stupid reason for picking a horse but produced one of my few winners.

I stuck to my system. That is better than any other kind of bet.

For whatever reason, my system has failed me at Kentucky Derbies.

I found a book called Racetrack Betting: The Professors’ Guide to Strategies by Peter Asch and Richard E.

The book bases the ability to pick horses on an economic theory known as the wisdom of crowds.

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Most of my equine knowledge was gleamed when I worked on the clean-up crew at the Kentucky Horse Park. His owner, Arthur Hancock III, had graduated from Vanderbilt and I had received a Masters Degree from Vandy the year before. The last one I remember winning was Sunday Silence in 1989.

The professors frown on exactas, daily doubles or any bet that exhibits large risk.

Like in the investment world, the winner at race track is the person with a conservative style and discipline. Just like the lottery, big odds draw a lot of excitement and attention.

Don McNay, CLU, ChFC, MSFS, CSSC is the founder of McNay Settlement Group in Richmond, Kentucky.

As the son of a professional gambler, people often ask me for betting advice. Quandi.

Although I started going to race tracks before I was able to walk, I don’t know much about the horse industry.

When I go to the track, I don’t look at the racing form, jockeys, past history or pick horses with funny names. I can sum up the advice in two statements.

The professors hate jackpots like the Pick-6.

The idea is that the marketplace will move with the crowd towards the best outcome. You can write to Don at or read his award winning, syndicated column at I stick to it today.

Thus the best advice may be to forget all the high powered systems and experts and give it your best guess.

Bet on the horse that everyone else is betting on. Slow and steady works in the financial markets and works at the track too. It is a driving force for web sites like Google.

If a horse moves from 10 to 1 to 2 to 1, it is probably a good horse to bet on.

Dad was superstitious and started to believe that my system was jinxing him. I can tell you what horses make the biggest mess.

Bet on the horse to show, not to win or place.

Just like the lottery, you don’t see many people winning them.

The professors said that betting to show will produce a winner 52% of the time. He would bet $100 on a horse and lose.

I usually win enough money to pay for lunch.

The wisdom of crowds concept is really popular now

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