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My boss gave me $100 to bet on the Kentucky Derby. Here’s how it went.

On Thursday afternoon, amid the chaos of what became three Kentucky Derby contenders scratching from the race on the same day, I stepped into the office of the Lexington Herald-Leader and was given $100 by my boss.

This was not some kind of reward for my hard work in the lead-up to Kentucky Derby 149, or even a bonus for strong reporting across the various sports that I cover at the newspaper.

This was money given for a purpose, with specific intent: You are to bet this $100 on the Kentucky Derby and write about it afterward.

It sounds like a dream to most people, to be handed money that isn’t yours with the express order to gamble it all on the most prestigious horse race in America.

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There would be no nickel-and-diming, no betting in dribs and drabs to hover around even.

I was going home broke or I was going home rich, but without a doubt I was going home with a story.

Naturally, the former seemed the most likely, before my mother ensured the latter occurred.

Lexington Herald-Leader sports reporter Cameron Drummond shares a laugh with Herald-Leader colleague Caroline Makauskas while researching bets ahead of Saturday’s 149th Kentucky Derby at Churchill Downs. Drummond bet on three different horses to win the Derby: Angel of Empire, Jace’s Road and Mage.
Lexington Herald-Leader sports reporter Cameron Drummond shares a laugh with Herald-Leader colleague Caroline Makauskas while researching bets ahead of Saturday’s 149th Kentucky Derby at Churchill Downs. Drummond bet on three different horses to win the Derby: Angel of Empire, Jace’s Road and Mage.

Last-minute preparations for a Pick Six

Every year for the Kentucky Derby, I join a smorgasbord of people that I am loosely connected to in a group chat and cobble together a Pick Six for Derby Day, starting with the Twin Spires Turf Sprint and ending with the Run for the Roses.

The threads that connect us are loose at best: Some are good friends from college that I talk to daily. They populate group messages with titles like “Hell of a Horse,” reflecting inside jokes that account for most of my daily laughter.

Others I would call college associates, people I shared classes and social circles with, but wouldn’t consider close friends.

Then there are the friends of the friends that rounded out the group message: I don’t have their contact cards. I don’t even know some of their names. It doesn’t matter. We’re united in the pursuit of profit. The cash for the almighty dollar.

The annual Kentucky Derby Pick Six is always meant to be well thought out, with a couple hours of research put in and sound gambling strategy involved.

That never goes to plan.

Inevitably, it’s an hour of quickly sorting through speed figures and past performances and hurriedly scanning BloodHorse race previews to gain insight.

You’ll be stunned to learn this doesn’t yield significant monetary returns.

Granted, I’m not the only person crunching the numbers and prognosticating the race results.

It’s a team effort. And a team failure.

How long did this year’s Pick Six last?

Precisely 1:02.45, which is how long it took Nobals to score a massive 38-1 upset win in a stakes-record time in the Twin Spires Turf Sprint.

Can’t wait to do it again next year.

Bet: $36 in total as part of a Kentucky Derby Pick Six.

Result: $36 loss.

Remaining amount: $64.

Lexington Herald-Leader sports reporter Cam Drummond does research before placing wagers on Saturday’s Kentucky Derby. Drummond’s lone winner was a win bet placed on Mage — at the request of his mother.
Lexington Herald-Leader sports reporter Cam Drummond does research before placing wagers on Saturday’s Kentucky Derby. Drummond’s lone winner was a win bet placed on Mage — at the request of his mother.

Another bet on Mendelssohns March

The Pick Six got us off sequence.

The plan for this Derby betting story was to divide it into five sub-sections, with five $20 bets featured.

That went out the window when the Pick Six buy-in was $36. So, we had to get back on sequence.

Enter the American Turf Stakes, where I could happily get back on schedule with a toss-away $4 bet on Mendelssohns March, a son of Mendelssohn last seen running sixth in the Blue Grass Stakes last month at Keeneland.

I joined fellow Herald-Leader reporter Ben Roberts and friend and horse racing aficionado, as well as ESPN Louisville radio host, Louis Rabaut, as a Mendelssohns March-backer in our official Blue Grass Stakes predictions.

So in the interest of believing in the horse, as well as a good bit, I backed Mendelssohns March again Saturday, knowing full well what was likely to occur.

He ran ninth in the American Turf Stakes.

At least we’re back in order now.

Bet: $4 on Mendelssohns March to win the American Turf Stakes.

Result: $4 loss.

Remaining amount: $60.

Lexington Herald-Leader sports reporter Cam Drummond does research before placing wagers on Saturday’s Kentucky Derby for the purpose of this article. Drummond spent the late morning handicapping the Derby after reporting on the favorite, Forte, being scratched from the race.
Lexington Herald-Leader sports reporter Cam Drummond does research before placing wagers on Saturday’s Kentucky Derby for the purpose of this article. Drummond spent the late morning handicapping the Derby after reporting on the favorite, Forte, being scratched from the race.

I picked Angel of Empire. So, I had to bet on him.

The initial plan was to put together a trifecta of the Kentucky Derby predictions that I officially made in this very newspaper.

Days ago, I proclaimed to the world that Angel of Empire would win the Kentucky Derby, with Forte in second and Derma Sotogake making history by becoming the first Japanese horse to ever hit the board in the Derby in third place.

My ability to replicate this on a bet slip was impossible, though, following the dramatic Saturday morning news that Forte scratched from the race.

So in the interest of still putting my money where my mouth was, we opted for a straight $20 win bet on Angel of Empire.

As a man who has incorrectly predicted every single sporting event this newspaper has asked me to predict — two Kentucky-Louisville football games, a Blue Grass Stakes and Kentucky men’s basketball’s 2023 NCAA Tournament outcome — I harbored moderate faith that this would be the time I’d be proven correct.

As it turns out, I still do not know ball.

Bet: $20 on Angel of Empire to win the Kentucky Derby.

Result: $20 loss.

Remaining amount: $40.

After Rich Strike, plan for the impossible

It was a given that one bet made during this exercise was going to be on the horse with the longest odds to win the 2023 Kentucky Derby.

After what Rich Strike did last year, how could you not toss some money on a unheralded horse, especially in a relatively unheralded Kentucky Derby field.

I wasn’t going to Mattress Mack the situation by waiting until the last possible moment to toss the wager down, so I went with an educated guess about 35 minutes before post time about who I anticipated the longest shot would be.

Jace’s Road was bet at 31-1 odds, and eventually closed at 33-1 odds. This was tied with two other horses — Raise Cain and Sun Thunder — for the longest odds in the race.

Jace’s Road made a brief appearance on the early pace out of the starting gate and was never heard from again, finishing second-to-last.

But you had to have something on him, right?

Bet: $20 on Jace’s Road to win the Kentucky Derby.

Result: $20 loss.

Remaining amount: $20.

My mother asked me to bet on Mage, so I did

My mother, Rosenilde, doesn’t know much about horse racing, or sports for that matter.

Born on a rural farm in the Brazilian state of Minas Gerais, she inherently understands soccer above everything else, and has also gained residual sports knowledge from my first 18 years of life, growing up in North Texas and watching Dallas-area sports obsessively.

But beyond knowing that Luka Doncic is a Maverick and Dak Prescott is a Cowboy, much of everything else escapes her.

For horse racing, she is like any casual viewer of the sport: She tunes in for the Kentucky Derby, once a year, and that’s it, although she’s become somewhat more interested since I joined the Herald-Leader as a sports reporter in July 2021.

She knows that I cover horse racing for a living, but that hasn’t made her more informed as a handicapper.

So at 1:21 p.m., at her request, I texted her a list of the Derby field: Only names, no odds. She wanted to pick her Derby horse based on name only, like millions of others around the world.

“I’m between Mage and Sun Thunder,” she texted back about two hours before the race. “Bet the one that you think has the most chance of winning.”

With the tiniest flex of my horse racing acumen possible, I elected Mage over Sun Thunder, given Mage’s strong showing in the Florida Derby last month and Sun Thunder’s uninspiring form entering the Kentucky Derby.

So, in this small way, I can claim I contributed to a 15-1 Derby winning bet.

My mother may not know anything about gambling or horse racing, but she knows when she’s won.

“Please tell me that you placed some kind of bet on Mage for me,” she texted, unprompted, less than 10 minutes after the race ended.

Yes, Mom, I did.

Bet: $20 on Mage to win the Kentucky Derby.

Result: $324 win.

Final amount: $324 won from $100 wagered.

What did we learn from this experiment?

For all the prognosticating and predicting that goes into horse racing, and the Kentucky Derby specifically, it’s astounding how often an outcome like this occurs.

Those who thought Angel of Empire’s strong Arkansas Derby was a harbinger of a Derby triumph (myself included) were wrong, as were those who thought the Japanese horses were finally set to break through at Churchill Downs.

Ditto for anyone backing a Brad Cox-trained horse, or who had an eye on the Todd Pletcher-trained Kingsbarns to become a rare winner of the Louisiana Derby and Kentucky Derby.

I only won money Saturday at Churchill Downs because my mother from Brazil texted me the name of a horse she liked.

She will also be handicapping the Preakness Stakes for me in two weeks.

Kentucky Derby 2023 complete order of finish and payoffs at Churchill Downs

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At age 45, jockey great Javier Castellano finally throws off his Kentucky Derby hex

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Mage’s magic in 2023 Kentucky Derby brightens a dark week for horse racing