Looking to make money betting on the Kentucky Derby? Here are eight tips

As I prepare to place a bet on this year’s Kentucky Derby, I think back to my first visit to a track. When I was about 12 years old, my father took me to Belmont Park in New York. Even then I felt that every bettor has a “system” – that is, a methodology for guaranteeing a winning day.

And on that first visit, I learned my dad’s system – a simple strategy that involved placing a show bet on the favourite, meaning that if our pick comes first, second or third, we stand in line for a payout. It seemed like a surefire plan: how could the top horse not take at least a third place?

Of course we lost our shirts.

In the decades since that visit, I’ve used many other systems when betting on horses. And yet I can count on one hand – actually on two fingers – how many times I’ve made money in the course of a day. This handicap business is clearly not for amateurs.

But there are professional handicappers, like people who play ponies for a living. And if you ask them for advice, like I did, they will happily share some of the tricks of the trade with you. So keep these eight tips in mind as you place your bets on this year’s Derby – or any other race in the future.

Buy The Horse Racing Bible (And Read It Thoroughly)

Investors have their go-to places for information (including, um, this website). And the horse players too – namely them Daily race form.

What makes the form so invaluable is all the information it provides on every horse in every race, including past performance, pedigree and responsible jockeys. These facts and figures (and I’ll get to some of them in more detail in a moment) lay the foundation for how every pro – and some clever amateurs – handicaps a race. Some handicappers spend an hour going through the form for each race.

Understand that speed makes the race

If there’s one factor that handicappers say shapes their view of how a race goes, it’s pace. When a race appears to be dominated by fast horses that are known to rush forward, a horse that normally lags behind can have a distinct advantage. (The theory is that the speed horses tire each other out as they get to the track.) Conversely, when there are a lot of “Cnaisers” in a race, a speed horse may be the best choice. (The theory is that by the time the closers await their move, the fast horse will already have opened an unbeatable gap.)

But how can a bettor determine the likely pace of the race? It’s about carefully reading the form, which not only shows how the horses have finished in their previous races, but also where they are placed at each stage (beginning, middle, and end, and other points in between) of those races.

Be a value investor (um, weather)

For handicappers, it’s not necessarily about betting on the “best” horse. Rather, it’s about betting on horses that have good value — the equivalent of Warren Buffett’s famous value-based investing approach. Handicappers are reluctant to bet on favorites because they usually go off at low odds (and only win about a third of the time), so the risk-reward equation is unappealing. Handicappers don’t like long shots either: what’s the use of a 50-1 bet if the horse really has no chance of winning?

Ultimately, the ideal horse is one that comes off with better odds than reality suggests: imagine the horse that should be 4-1, but offers an 8-1 payoff instead.

Know when to ask, “Who is your daddy?”

You’ll hear a lot of people in the racing industry talking about pedigree like the sire and dam of a horse. The belief is that success breeds success—or else why talk about tens of thousands of dollars in “stud fees”? Handicappers will tell you that pedigree counts, but mostly in cases where there isn’t enough hard data to indicate how a horse will run. For example, if it’s the first time a horse has ridden on grass (as opposed to the more standard dirt tracks), it might be worth seeing how mom and dad handled grass.

Think exotic

If you only place win, place or show bets then you are probably not a pro. Severely disabled like “exotic” bets – these are exactas (predicting the top two finishers in a race in exact order), trifectas (top three) and superfectas (top four). Another type of exotic is to pick winners in multiple races – say, pick three (three races in a row), pick four (four races), or pick six (six races).

The appeal is obvious: the more complex the bet, the bigger the payout (some winning Pick 6 bets have paid out millions). Given how little a straight win bet usually pays out, those bigger payouts are often the key to making real money. And as my first experience at the track confirms, trying to make money from show betting is an even more daunting challenge.

Don’t forget the jockey

In racing, horses don’t live in a bubble – they need a jockey to guide them from start to finish. And while handicappers generally pay more attention to the animal than to the man (or woman) on the animal, they don’t completely ignore the jockey either. A handicapper told me to look for a jockey with at least a 12% winning record. It may not sound that high, but in a competitive field, 12% is “a good thing,” the handicapper advised.

Be fashionably (and profitably) late

Handicappers are probably not the first to place their bets. And there is a reason for that – actually two reasons. First, since the odds are constantly changing, handicappers can’t fully determine the “value” until it’s fairly close to post time – like the last two minutes. Otherwise, that 8-1 value bet could turn into a not-so-value 4-1 bet. (Which isn’t to say handicappers don’t do their homework hours in advance. Still, they’re willing to adjust their betting strategy based on those last-minute odds.)

Also, handicappers like to have a look at the horses when they come out on the course – about 10 minutes before the race. This allows them to see if the horse is happy and ready to go (an arched neck is a good sign) or if the horse is stressed (sweating or “frothing” is a worrying warning).

Perhaps the smartest bet is no bet at all

Sure, every race is fun to play. But handicappers are a selective group – they favor races where there is value and skip others where they just don’t see a risk worth taking. Of course, this advice applies best if you’re spending a day at the track and have multiple races ahead of you. With the Derby you speak of a unique opportunity. However, proceed with caution. Looking to make money betting on the Kentucky Derby? Here are eight tips

Brian Lowry

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