A Non-Bettor’s Guide To Betting The Kentucky Derby

So the 147th Kentucky Derby, America’s greatest Thoroughbred horserace is back to its historic place on the calendar: The First Saturday In May (the title of what I think is the best documentary ever made about America’s most historically prestigious race), this Saturday, May 1.

In my opinion—well, most of what you’re about to read is my opinion—there are only two reasons why people like horseracing. First, they love horses; second they love betting on horse racing. There’s a mix of the two, but that mix is kind of like oil and water. Shake it and it mingles for a while, then separates.

Now, in the U.S. today, there are many more of the bettors than of the horse lovers. That’s just an observation based on the number of people who laugh at me when I tell them I spend silly sums of money to hang out at racetracks around the world because I love the horses while I refrain from betting on them.

Now, bettors—they prefer the term handicappers—spend a lot of time researching their choices. They’re sometimes called wiseguys. They pore over Beyer and Brisnet and Thoro-Graph speed figures. They talk about which horse is “the speed,” which runs “off the pace,” which is the “closer” and things like the post position, the track, the weather. All sorts of stuff.

I ignore all that ‘cause, as I like to say, all the handicappers I know have day jobs.

Now I’ve been writing about this for over a decade, so I do have some insight into how to bet. And while I don’t bet much—I’ll get to that—I’ve covered the Dubai World Cup since 2010 and picked the winner seven of 11 times. Really.

In fact, a well-placed handicapping friend in the industry likes to call me “MISTER! Monterosso” when he sees me because I called the winner, poorly regarded Monterosso, before the start of the race in 2012 as I left the press room for the track at Meydan.

The 3-1 favorite that day was justifiably (no pun intended) Game On Dude, then a two-time winner of the Santa Anita Handicap (G1), and he’d win a third time. Breeders’ Cup Ladies (that’s what they called it then) Classic (G1) winner Royal Delta was also in the race.

Ahhhhh! Cliché alert: I had a method to my madness. In the Dubai World Cup, I chose the runner-up from the previous year’s running of the race if they ran the following year. That worked with Well Armed (2009, second to Curlin in 2008), Gloria de Campaeo (2010, second to Well Armed in 2009), the aforementioned Monterosso  in 2012 (second to Victoire Pisa in 2011) and California Chrome in 2016 (second to Prince Bishop in 2015).

Yeah, laugh at me now wiseguys!

Okay, so now that I have your attention…

…everything you’re about to read is personal conjecture. So, if you’re wise (and even not a guy), you’ll avoid any suggested recommendations.

How to bet

Now there are a number of ways to bet. Think of it like the stock market. You can buy one stock, or a few to spread the rise, like a mutual fund.

So, first, let’s think stock market. Think Amazon, Google (now Alphabet) and Apple.

There’s win/place/show bets—first, second and third. On the nose, as they say.

There’s the Exacta, which is winner and placer in the correct order; the Trifecta, win, place and show in order; and the Superfecta, the first four finishers in order.

These are called “Exotics.” I call them “Good luck with that!”

My preference is the Trifecta or Superfecta because, in most instances, I only lose 50 cents or 10 cents respectively. Think the nickel slots in Vegas.

The largest bet I ever placed was $1 in a reporter’s pool during one of the Dubai World Cups…one of the four I lost.

Now, think mutual funds. You win more if you’re correct betting on the nose and especially in the correct order of finish and at longer odds, the Exotics. But it makes sense these tend to be more difficult.

So, many bettors opt for a box for the Exacta or Trifecta. You pick two (Exacta) or three (Trifecta) and you win if you’re correct in any order.

You’ll be able to read reams of stuff about how to bet on any number of betting sites, but what you just read is pretty much it.

End of tutorial.

Getting into the Kentucky Derby

Let’s start getting serious by taking a look at this year’s Derby field.

There have been a number of systems over the years to determine the entrants. Now, there’s a point system awarding a certain number of points for placements in certain prep races.

Think the NCAA March Madness Basketball Tournament “bubble.”

This year, for example, the favorite Essential Quality (more about him later) has the most points, 140. The last entry, Brooklyn Strong, has only 10.

The disparity is because of the number of horses that might otherwise qualify on points, but suffer mild injury or are just deemed plain not ready by their trainers as they proceed along what is known as The Derby Trail, the series of prep races mentioned and the four months of training that precedes the Derby.

So, Brooklyn Strong, King Fury and Keepmeinmind were “on the bubble,” but got in because horses with more points were removed from the race by their connections.

Betting the Kentucky Derby: by the numbers, the jockey silks, the colors and other methods

The Kentucky Derby is a notoriously difficult race to handicap—we’ll call it that from now on.

For one thing, there are 20 thousand-plus pound horses in the starting gate stretched literally across the most iconic dirt racetrack in America at Churchill Downs in Louisville, Kentucky—all released from the gates and fighting for position at the same time.

Think rugby scrum.

Now, these all are young horses, relatively inexperienced three-year olds. They’ve never experienced anything like this before.

Think middle-school freshmen.

Since it’s so difficult to predict, many handicappers will rely on history. For example, no horse has ever won from gate 17. Like ever.

So forget him. Sorry, Highly Motivated.

Back in the day, eight horses won from gate 1, starting right at the rail. Not in recent times—the last was Ferdinand in 1986. Think 19 thousand-plus pounds rushing at you all at once at the start. Sorry, Known Agenda. Well, maybe not, wait for that.

The best post position seems to be number 5. It has 10 winners, is tied for the most runners-up and the highest winning percentage, nearly 11 percent. In recent years, California Chrome (2014) and Always Dreaming (2016) won from  post position 5. Congratulations, Sainthood, your connections’ prayers were answered!

Still, the best positions are thought to be somewhere in the middle, a pretty good place to be for stalkers that run “off the pace” and closers that like to make a single big run in the stretch. Traditionally, that was post positions 7 through 14.

Now this is a little complicated. It used to be that Churchill used a 14-post starting gate and added a six-post auxiliary gate for the Derby. That’s because the maximum field for a race at Churchill was 14 horses, except for the Derby when it was expanded to 20 horses.

But last year, Churchill added a brand spanking new 20-post starting gate. The new gate helps the horses in post positions 1 and 20 by moving post 1 a bit off the rail and post 20 a bit in. Congrats Known Agenda and Bourbonic!

That explains in part why Known Agenda, a horse that drew the dreaded post 1 position is still the third betting choice at 6-1.

The other reason Known Agenda is considered a good bet is because of his jockey, Irad Ortiz Jr. This guy is a winning machine. He’s been the Eclipse Award-winning jockey for three consecutive years. As I have written before, Irad could win on a donkey racing backwards, he’s that good.

Most recently, he rode little-known Letruska to a nose win over the great Monomoy Girl in the Apple Blossom (G1).

Ortiz was the nose.

Betting the names

People who have a life and don’t spend their time handicapping races have pretty simple methods of choosing winners.

One popular method is the horse’s name. A recent favorite was Tapit’s son Frosted, a lovely gray. Get it? He had a pretty good career, even finishing second to Triple Crown winner American Pharaoh in the 2015 Belmont Stakes.

Speaking of American Pharaoh, he’s only horse to win the quad: The Triple Crown plus the Breeders’ Cup Classic in 2015. His sire was the late Pioneer of the Nile. Get it?

But the really fun thing about his name is that it’s misspelled, the “a” and “o” incorrectly inverted. Story goes it was the result of a naming contest in which the winner misspelled Pharaoh and the owners were just stuck with it.

My personal favorite is that of 2011 Derby winner, Animal Kingdom. Weird name, until you consider his sire was Leroidesanimaux—King Of The Animals.

Now, this year, there are some cool names. There’s the favorite, Essential Quality. What more needs to be said? There’s King Fury, which sounds like the title of a Marvel Comics film, with Like The King in a supporting role. Hot Rod Charlie sounds like he can dash across the track, Helium can float over the competition and Sainthood is undoubtedly the Pope’s choice.

Some folks think Rock Your World will and that Brooklyn Strong is. Bourbonic sounds like a tad too much Midnight Bourbon and Highly Motivated is said to be. Oh, and keep in mind Keepmeinmind  ‘cause you just never know.

I’m betting they call Hidden Stash ‘Cannabis’ at the barn.

Betting the colors

There are three ways you can bet the colors. Each horse has a numbered saddle cloth with a certain color. You can see those colors on the post position chart.

My own favorite is 8, electric pink, because that was the number of the cloth one of my favorites, Barbaro, wore. All horse lovers know the tragic story of Barbaro. The winner of the 2006 Derby, Barbaro suffered a severe leg fracture two weeks later in the Preakness.

The owners—the respected Mr. & Mrs. M Roy Jackson—were determined to save the horse’s life. He received the best veterinary surgery and aftercare for eight months. People from all over the world followed his story. They sent him cards and gifts and prayed for his well-being.

It seemed he would fully recover. Then, he finally developed and succumbed to the dread disease laminitis, an inflammation of the soft tissue around the hoof that is unbearably painful. A fund now exists for research into a cure for this puzzling malady.

A lovely full-size bronze statue of Barbaro graces the entrance to Churchill Downs. People still leave flowers there.

Barbaro was foaled April 29, 2003. Happy Birthday, Kentucky Derby Champion, and rest in peace.

Now, there are the colors of the jockey silks, those distinctive blouses and caps jockeys wear, each emblematic of the horse-owner’s stable.

My own favorite color is royal blue. That just happens to be the color of the uniform worn by my grade school football team. They never gave it to me to wear but, see, I’m not bitter.

I have a woman friend who is a presenter on the television broadcasting side of racing. She refers to it as a “cheater color” because she believes every woman looks great in a royal blue on raceday. Agreed.

Royal blue is the color of Godolphin silks and will be worn by jockey Luis Saez on Derby favorite, undefeated Essential Quality. Saez, you may remember, crossed the Derby finish line first two years ago on Maximum Security, but suffered a disqualification for interference. And Godolphin is owned by Sheikh Mohammed of Dubai. He’s been in hot pursuit of a Derby win for a couple of decades with no luck. Except maybe….

So, looking good Essential Quality! Keep him in straight path, Luis, and best of luck, Sheikh Mo!

The final color choice is the color of the horse. Thoroughbreds come in several shades from Chestnut, a lighter brown; to Bay, a medium brown, to near black. But just about everyone’s favorite color is gray.

Gray is the color of Tapit; remember, Frosted’s dad. He’s a very popular sire. But the thing is none of his progeny have ever won a Derby. No one quite knows why, so they make up reasons. The most popular one is “Tapits can’t make the (mile and a quarter) distance” or “Tapits are unruly.”

Tapit himself is notoriously unruly. Derby followers will remember another Tapit son, Lani, from the 2016 Derby. Or Just Plain Crazy Lani as he came to be known. Lani would stop dead in the middle of a workout, refusing to run. Or continue to run after a workout, refusing to stop. He liked to whinny at and try to bite other horses. Though he wore saddle cloth 8, my favorite remember, he was walked out first in the pre-race post parade to avoid any unpleasant confrontations with 1 through 7.

I loved him.

Now Essential Quality is a gray and another son of Tapit. But he’s reputed to be very manageable. So, you can see where I’m at.

A final method

Okay, so that takes care of all the favorite methods. But I have a final thought.

Becky Schroeder, a dear friend of mine, lives near Louisville. A retired teacher, she’s known as Miss Becky to her lifelong trove of adoring students, many of whom still keep in touch with her. Becky also worked for years at the Derby Museum, usually hosting guests on Derby Day so she couldn’t enjoy the race.

Well, she retired from that job too this year, so she and husband Joe will get to enjoy this year’s Derby. Yesterday, as I pored over Beyer, Brisnet and Thoro-Graph numbers; as I considered the post-position draw and the wisdom of my saddle cloth, silks and horse color choices; as I examined the weather forecast, I received an e-mail from Becky.

Now, we all know teachers are wise. But Miss Becky has a particularly strong following as a wiseguy as well. Apparently, Becky’s colleagues know that, too.

‘Cause see, though Becky is retired from the Museum, she just returned from a “speaking engagement” in Louisville before a “special group of people” about the Kentucky Derby. Hmmmm.

The e-mail forwarded to me was written and sent to her by Dan McCamish, a former Principal of Becky’s when she taught. As you can see, it acknowledges all the horses who will run in Saturday’s Kentucky Derby.

Becky agreed to share it.

Miss Becky— Or should, as I told my royal friend KING FURY, GET HER NUMBER as she is LIKE THE KING, a person of ESSENTIAL QUALITY, a DYNAMIC ONE, HIGHLY MOTIVATED who has a KNOWN AGENDA that can ROCK YOUR WORLD so you might gain her insight into the derby entries. Even when she plays her MANDALOUN, singing her BROOKLYN SONG, she is rising high like in a HELIUM balloon to get to that MEDINA SPIRIT so she can pick the winner. But, will she share her SUPER STOCK of knowledge that will place her in SAINTHOOD amidst us poor bettors with no clue as to what to do. Perhaps if we can ask her to go to her HIDDEN STASH and have a SOUP AND SANDWICH with her MIDNIGHT BOURBON she will become BOURBONIC and utter the winning name. KEEPMEINMIND if you do. O BESOS are on hold until we hear from you. Your friend HOT ROD CHARLIE

Now, here’s a photo of Becky and husband Joe in front of the statue of Aristides, the first Kentucky Derby winner in 1875, as they enjoyed a day in the sun earlier this week at Churchill.

Want some proof Becky is a lucky charm? Husband Joe is on the mend after surviving the literal crash of a small private plane in June, 2019. Joe’s getting better; the plane, not so much.

So, it’s pretty obvious that Becky can pick winners. As for her pick, she’s mum. But her favorite jockey is “Money” Mike Smith and he’s on 20-1 longshot Midnight Bourbon in post position 10, smack in the center of the field.

Just sayin’.

Cheers! And, as they say all over the state of Kentucky on the First Saturday in May: Happy Derby!