Inside Secrets to Winning Big on the 2025 Kentucky Derby and Oaks Straight Bets and Exotics at Churchill Downs

They say the Kentucky Derby is all about the thrill of the main event on that first Saturday in May, but honestly, the real action kicks off earlier—call it Thurby, the unofficial curtain raiser where the Kentucky Oaks stakes its claim. Now, if you’ve ever wondered whether you can double down on the drama and dough, the “Kentucky Oaks-Derby Double” is where savvy bettors separate themselves from the crowd. It’s one of those rare bets where picking back-to-back winners on Friday and Saturday isn’t just a pipe dream but a genuine possibility—with the right insights, of course.

Before I dive into the horse-by-horse rundown and my hot takes on who’ll stomp the fields this year, let’s rewind for just a sec. Betting on horse racing isn’t a simple win/lose affair. Oh no, there’s a charmingly tangled web of win, place, show, and the alluring ‘Across the Board.’ Then come the exotics—exacta, trifecta, superfecta—that spice things up for anyone chasing those sky-high paydays. Want to hedge your bets? Box ‘em. Have a standout favorite? Key ‘em. It’s like putting frosting on the cake while keeping your eyes peeled for the crumbs.

So, without further detours or needless fuss, let’s saddle up for my picks on the Oaks, the Derby, and that ever-so-sweet double thrill ride. Whether it’s analyzing early pace kings, forecasting the muddy dance to come under looming thunderstorms, or dissecting pedigrees richer than bourbon, we’re about to get into the thick of it—because if you’re not living on the edge during Derby weekend, what’s the point?

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While the main event is Saturday, the 2025 Kentucky Derby weekend technically began on Thursday, aka Thurby, with the Kentucky Oaks as the featured race on Friday. One of the coolest things a sports bettor can do is hit the “Kentucky Oaks-Derby Double,” picking the winner for the big races on Friday and Saturday. 

Before discussing my picks, here’s a brief-ish reminder of ways to bet on horse racing that I wrote in last year’s Kentucky Derby article. You can bet a horse to win (first), place (second), and show (third) or “Across the Board”, which is betting on all three. There are exotics such as exacta, trifecta, and superfecta for those searching for massive paydays. 

In an exacta, you bet 2+ horses to finish first or second. A trifecta includes 3+ horses for the win-place-show. A superfecta is 4+ horses to finish 1-4. By “boxing” an exacta, bettors can win if at least two of their picks win or place. The same goes for trifecta and superfecta boxes. “Keying” an exotic allows you to put your winner “up top” with horses underneath to finish in any order. 

Without further ado, let’s get into my Kentucky Oaks, Derby, and double picks. 

Thirteen horses on a 1 1/8-mile dirt track for 3-year-old fillies with a $1.5M purse. 

The starting gate is perfect for Simply Joking, who has the fastest “early pace” in this field. She has run faster in all three races and won her only start on a wet track. This might be useful because the weather forecast indicates a two-thirds chance of rain and thunderstorms around post time. 

Simply Joking has back-to-back strong workouts clocking 47 seconds in four furlongs and 58 seconds in a five-furlong work at Churchill. For context, 12 seconds per furlong is considered fast. We are getting a good number since she’s been priced between $1.70-$3 in her first three races. 

This jockey-trainer combo won the Kentucky Oaks last year with Thorpedo Anna. Take Charge Milady had two consecutive strong workouts recently: 59 seconds over five furlongs two weeks ago at Churchill and 47 seconds over four furlongs at Oaklawn March 30. All of her races have been at least one mile long. She is 2-1-0 in four starts this year with a win by four lengths on a wet track. 

No one likes using favorites, especially in horse races, but Good Cheer’s undefeated record speaks for itself. She is coming off her fastest race, (tied for the fastest speed in this field), winning the Grade 2 Fair Ground Oaks by 3.5 lengths in March. Her tactical speed works for the No. 11 starting gate, and Good Cheer has won three times at Churchill. 

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Nineteen horses on a 1.25-mile dirt track for 3-year-olds with a $5M purse. 

He had a blazing-fast workout at Churchill Down on Monday, running five furlongs in just 58 seconds. Citizen Bull faded at the end of the Grade 1 Santa Anita Derby last month, finishing fourth, 9.75 lengths behind the Kentucky Derby betting favorite, #8 Journalism. Before that, he won three consecutive graded stakes races, including the Grade 1 American Pharoah and Grade 1 Breeders’ Juvenile Cup. 

These are the best odds of Citizen Bull’s career, and he has one of the fastest “early paces” in the Derby, so the No. 1 post suits him well. Hopefully, Citizen Bull learned from his disappointing finish at Santa Anita and has enough in the tank to finish strong at Churchill. At these odds, I’ll use him in my trifecta and bet him across the board. 

There’s a 90% chance of rain in Louisville on Saturday, so these horses will likely race on a sloppy/muddy track at Churchill. Luxor Cafe has three wins and a place in four starts on wet tracks. Also, Japan’s horse racing is on the rise, and a Japanese thoroughbred, Forever Young, lost in a photo finish in last year’s Kentucky Derby. 

Luxor Cafe has run faster in five consecutive races with a four-race winning streak, including three straight stakes races, and has been the favorite in every start. The No. 7 horse’s speed ratings are slower than the favorite’s, Journalism. But, Luxor Cafe starts alongside the No. 8 horse, and he’s a strong closer, so he can draft Journalism and pass him on the home stretch. 

Furthermore, Luxor Cafe has “championship DNA” in his blood, and he’s raced in bigger fields than the favorite. His sire is American Pharoah, the 2015 Triple Cup and Breeders’ Cup Classic winner. Four of Journalism’s five career races have been five-horse fields, with the other having nine rivals. In contrast, Luxor Cafe’s smallest field is 10 horses. 

This will be a fast race. There is a lot of speed starting on the rail, and the No. 20 horse, Owen Almighty, has the quickest “early pace” in this field and has to get out to a fast start. Given Luxor Cafe’s odds, which should get higher closer to post time because no one is touting him, and his pedigree and experience in big fields, the No. 7 is my favorite bet for the Kentucky Derby. 

I’ll disclose my bias up front: I’m from Saratoga and Sandman breaking his maiden at The Spa matters to me. However, the Grade 1 Arkansas Derby winner has “hit the board” in four of his five career stakes races. The No. 17 horse beat two Kentucky Derby rivals at Arkansas and “his huge closing kick fits very well here in a race loaded with gate speed,” per the Daily Racing Form. 

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