2024 Kentucky Derby Wagering Guide
Budgets $250-$500-$1,000
*Note - This is long, but hopefully, it will be worth your time. Assuming you have some success this week, do your part and donate to a reputable aftercare charity. Thanks - Tyler
If you like this format, make sure to like the post! This year, I’ve enlisted help with the Wagering Strategies. Eric DeCoster, who has spearheaded the Kentucky Derby Blog Content and covers Keeneland and Kentucky Downs extensively, will offer his thoughts and strategies to supplement the guide.
Ticket construction and overall wagering strategy deserve more attention. However, the appropriate wagering strategy largely depends on one’s budget and goals. The number of iterations is limitless, so most pundits ignore this topic.
Most of the current discussion (primarily on social media) on the subject is harsh criticism instead of constructive feedback. The keyboard warriors assume they know what’s best for you despite not knowing your bankroll and expectations. We’ll refer to them as the EV (expected value) Police. If they’re reading this, I expect to receive plenty of flack—I welcome it.
Along with Eric, I plan to cover several budgets for the Kentucky Oaks and Kentucky Derby cards. We will outline approaches for budgets of $250, $500, and $1,000.
To understand the wagering strategy, we must explain our handicapping opinions so you can see how we plan to leverage them at the windows. You may disagree with our handicapping but might be able to gain insights into how we think through our approach. Put differently, the idea here isn’t that you tail our suggestions but that you take your opinions and, hopefully, think about the best way to spend your budget.
Before we jump in, I want to provide a couple of generalities about bankroll management.
Review your Records
Regular ITM listeners know the importance of keeping wagering records. Luckily, most ADWs do the work for you.
Spend some time digging in and identifying your strengths. Specifically, you’ll want to arm yourself with your ROI by wager type. Generally, this is readily available and allows you to identify areas of strength and weakness.
Simplify your Approach
Part of the allure of Kentucky Derby weekend to most horseplayers is that most races feature bulky, competitive fields and larger-than-normal pools. And with the Kentucky Derby, it’s the only domestic race that will feature 20 runners. As a result, the payoffs can be huge, but one must recognize the level of difficulty increases exponentially.
If you’re a horizontal player who likes to play the Pick 5, consider playing the Pick 4 instead. Likewise, if you typically only wager on the Pick 4, try focusing on the Pick 3.
By simplifying your normal approach, you might miss out on a larger score but given a limited bankroll, it’s more likely that you might be undercapitalized and whiff entirely if you stick with your standard approach. This a reminder that the takeout on losing wagers is 100%.
If you disagree with this suggestion, surely you can agree not to go the other way. That is, if you’re usually a Pick 4 player, don’t be tempted by the Pick 5 or 6 on Derby day.
This is something that Steve Byk has suggested for years, so I want to give him credit here.
Finally, the Kentucky Derby is certainly not a time to forget about the simplest weapon in the wagering arsenal - The win bet.
Maximize your Opinions
It’s hard for many horseplayers to pass races once you’ve handicapped them and formed an opinion. This is true on a random Thursday at Gulfstream Park, let alone two of the sport's biggest days.
But it’s unlikely that your opinion is equally strong in all races, and a disciplined approach can be the difference between a winning and losing weekend.
You don’t need to participate in every Pick 3 or Pick 4. Identify your strongest opinions and figure out the best way to exploit that opinion in the pools.
To be clear, I’m not suggesting you limit your bankroll. Instead, I’m advocating that you leverage it in accordance with the strength of your opinion.
The wagering menu this weekend is daunting. On one hand, it’s good to have options, especially innovative ones. But participate only where you have a perceived edge.
Don’t be a Hero
This will seem somewhat contradictory to what I just suggested, and it is, to a degree.
The Triple Crown and Breeders’ Cup cards offer the most acceptable opportunities to spread (my opinion).
To illustrate my point, I’ll refer back to the 2015 Preakness. Yes, I’m going to redboard here. My opinion in that race was that American Pharoah couldn’t lose and that Divining Rod would relish the slop and hit the board. With that in mind, I constructed two Trifecta Tickets.
$5 AP / Divining Rod / ALL
$5 AP / ALL / Divining Rod
Tale of Verve finished second at 29-1 and Diving Rod rounded out the Trifecta for a ~$2,500 score. My rationale for using ALL in that spot was due to the rain (anything can happen) and the fact that I didn’t have much of an opinion on the remaining runners. Since Divining Rod figured to be the 4th or 5th choice, it seemed like an okay bet to make - two very strong opinions were salvaged by spreading where I didn’t have an opinion.
Thus, my strategy for these big days is a balanced approach using the last two concepts.
My Handicapping Assessment
Again, for the wagering strategy to make sense, we must explain our handicapping opinions. I have focused my written analysis on the Grade 1 races.
La Troienne Stakes:
This time last year, Idiomatic was simply a listed stakes winner. Needless to say, she had a pretty solid second half of the year. If she comes back in similar form, and there’s no reason to suggest otherwise, she will be hard to run down.
Xigera is the most likely upsetter, and trainer Phil Bauer won this race last year. There’s nothing wrong with Pretty Mischievous, but I wonder if she can run down horses of this quality.
Eric - I don’t believe Idiomatic would’ve been brought back to the races if she hadn’t maintained, or dare I say improved upon, what she was in 2023. She should make the lead and control things, but I do also believe Xigera is a viable candidate as the most immediate presser to that controlled pace and a horse coming in with stellar form.
Kentucky Oaks:
First off, I hope the weather cooperates. This is the preamble every year, right?
A lot has been made about the competitiveness of the Kentucky Oaks field. No disagreement here. That said, I believe Ways and Means or Just FYI will win the Oaks. And that’s a pretty firm opinion.
What happens behind them is anyone’s guess. I cannot confidently build vertical wagers for this race. The majority of my Oaks exposure will be in the form of Horizontal (Multi-Race) wagers, and I’ll need one of them to get the job done.
Eric - This is the deepest rendition of the Oaks we’ve seen in a while. Hell, with at least one of the also eligibles making their way into the field, the race is even tougher! I am firmly against Thorpedo Anna, Tarifa, and Leslie’s Rose the closer the race gets. I can’t envision them getting the pretty trips that saw them catch their recent signature wins. Just like Tyler, that leaves me with Ways and Means and Just FYI. Both should be fit to fire second back.
Derby City Distaff:
It seems like the winner will come from the Madison alumni. And the race looks to be run at a blistering clip. I like Vahva in this spot. She likely goes off as the favorite and I’m okay with that. Second off the bench, loves the CD track (albeit a slightly different surface) and has finishing ability. Chi Town Lady would be an interesting underneath horse and one that might be a good underneath key since she’ll be passing horses late. Finally, Three Witches might be forgotten and likely offers some value in this spot for very capable connections.
Eric - I agree that Vahva is the one to beat in her second start off the layoff. The race sets up perfectly for her. That being said, Alva Starr can’t be completely disregarded because of all that she overcame to beat Vahva last time out in the Madison. She seems like the rare type who can overcome whatever race shape is thrown her way. I think it’s wise to go closer-heavy underneath with the likes of Chi Town Lady and Sterling Silver.
Churchill Downs Stakes:
It seems as though every time trainer Jason Cook enters Three Technique, the speed horses stay in the barn. This is an ambitious spot, and I wish he had a prep, but I’m going to continue chasing this horse.
Unfortunately, I don’t have a strong opinion in this race.
Eric - Tyler mentioned the lack of speed and I completely agree. That leaves me with two solid options on flow and form, Zozos and Hoist the Gold. If these two can take care of each other they may just merry-go-round this race.
Turf Classic:
This race seems void of speed. Never Surprise is the likely pacesetter and I’d expect one or both of the Chad Brown runners to press/stalk.
Program Trading likely gets first run. I’m Very Busy is still searching for his Grade 1 victory. Both have a big shot.
Naval Power (GB) gets an extra furlong for his second Stateside attempt. Maybe there are some clues as to how well Appleby and the Boys in Blue are going by this race?
Finally, Integration might be able to save ground and turn the tables (on Naval Power) this time around. But the other Shug horse is most intriguing in this spot as he was pace disadvantaged in his prep.
I’m confident I’m mentioned the winner above, and I might side with the best-value horses as A’s - Never Explain and Program Trading.
Eric - This race does present a tactically tricky setup, but I will bank on Flavien Prat reverting Program Trading to his early form and using him forwardly. As Tyler referenced, this should place him well in the opening stages to get first run on some talented closers. I can never leave a Charlie Appleby trainee out of any stateside race, in which Naval Power HAS to be involved on my tickets.
Kentucky Derby:
My typical approach in the Kentucky Derby is to assess the runners based on speed figures and then assess who’s most likely to “run their race.”
Few horses actually run a new lifetime top in the Kentucky Derby. That means I start by identifying those that have already run fast enough and try not to focus much attention on horses that need significant improvement to contend.
From there, it’s a matter of race design and relative value.
Catching Freedom is the horse that appears most likely to run his race this year. And it seems like that should get him in the super under any scenario I could envision.
Despite being a ThoroPACE “downgrade” - I can’t be fully against Fierceness given his figure edge on this bunch. In fact, it seems clear that he’s the most likely winner of this race - Something that I’ve become more convinced of as the week has progressed. The ThoroPACE Forecast for the Derby is +35. This is based on objective data, and as a result, doesn’t take into consideration jockey/trainer intent or the cleanliness of the break. The speed horses and their connections are sending mixed signals. Track Phantom is adding blinkers but Steve Asmussen doesn’t expect him to be on the lead - His work seemed to confirm. The same could be said for Dornoch and T O Password. They are working as if they won’t be on the lead. On the other hand, it’s always dangerous to ignore objective data in this game…
I also like Forever Young (JPN); he will be my official pick, but I don’t have the confidence to fully trust him.
For the second year in a row, my “strongest” Kentucky Derby opinion involves a longshot that I think can hit the board. I think Domestic Product finally gets a pace that will let him show his ability (He exits the two slowest races, pace-wise, on the entire Derby trail). I don’t think he’s a likely winner. And his price is likely worse than what I thought it would be this time last week. Still, he should add value to any wager assuming it cashes.
In summary, I’m not opposing any of the logical contenders. I don’t love Fierceness, but I don’t want to lose if he wins and Domestic Product hits the board. The chart below lays out how I see the contenders.
***Note: Even with $1,000, I’d feel undercapitalized for the Pick 5 or Pick 6 that ends in the Kentucky Derby. The American Turf is the race that makes most of these multi-race wagers unapproachable, in my opinion.
Eric - After the post position draw I immediately came to the conclusion that a closer would win this Kentucky Derby. With Dornoch drawing the rail I think the pace will be contested and cause a lot of havoc in the second and third flights early on. As such, I am firmly against Fierceness in this race. While I understand the brilliance in his wins, I simply can’t ignore his losses and think the Derby shapes up only to his detriment.
That leaves me with the closers. It’s fair to say a horse won’t get the right trip from that far back in a race this big, but it’s simply too hard to predict who that would be. This means I just have to pick the best closer and that is clearly Sierra Leone. He seems to be able to make his own luck and his turn of foot is devastating compared to the other off-the-pace types, quite a few of which he’s beaten.
I believe Catching Freedom must be included in any verticals as he is consistent as the day long and has the right rider to perform well in the Derby. All in all, I’m prepared to go to battle saying those are my only win contenders.
I completely agree with Tyler that Domestic Product is another valuable type to keep involved underneath because of how the race draws up and how his figures do not reflect his true ability. Two others I will consider in those verticals are Mystik Dan on an off track (as another good closing option) and Stronghold on the assumption that he does take back further off the pace than one would expect.
***After reading Eric’s analysis, I’m more confident in my opinions, which makes this task a little easier. As a result, we will be more aggressive in some spots.
$250 Wagering Strategy
Assumption - Prefer action on Kentucky Oaks and Kentucky Derby
Assumption - Want to minimize loss of bankroll while taking some small shots at a big payout.
SHOW PARLAY (START WITH $30)
*Bet half of the starting amount, and roll all winnings into next show bet
Friday Race 5: 6 Xigera
Friday Race 11: 13 Just F Y I
Saturday Race 6: 10 Vahva
Saturday Race 9: 5 Legend of Time
Saturday Race 11: 5 Program Trading
Saturday Race 12: 4 Catching Freedom
OAKS EXACTA:
$10 EX BOX 11,13 = $20
OAKS - DERBY DOUBLE:
$5 11,13 / 2 = $10
$3 11,13 / 4,11 = $12
$2 11,13 / 15 = $4
$10 11,13 / 17 = $20
OAKS - TURF - DERBY PICK 3:
$2 11,13 / 5,9,11 / 17 = $12
$1 11,13 / 5,9,11 / 2,4,11,15 = $24
KENTUCKY DERBY EXACTA:
$2 KEY BOX 2,11,17 / 4 = $12
$2 KEY BOX 15 / 2,4,11,17 = $16
KENTUCKY DERBY TRIFECTA:
$0.50 4 / 2,8,11,17 / 2,3,7,11,15,17,18 = $12
$0.50 2,8,11,17 / 4 / 2,3,7,11,15,17,18 = $12
$0.50 2,8,11,17 / 2,3,7,11,15,17,18 / 4 = $12
$1 17 / 4 / ALL = $18
$1 17 / ALL / 4 = $18
KENTUCKY DERBY WIN-PLACE-SHOW:
$6 on 4 = $18
$500 Wagering Strategy
Assumption - Want action on Oaks and Derby primarily but open to some multi race wagers
Assumption - Looking to turn $500 into $2500 or more, would be okay breaking even
SHOW PARLAY (START WITH $30)
*Bet half of the starting amount, and roll all winnings into next show bet
Friday Race 5: 6 Xigera
Friday Race 11: 13 Just F Y I
Saturday Race 6: 10 Vahva
Saturday Race 9: 5 Legend of Time
Saturday Race 11: 5 Program Trading
Saturday Race 12: 4 Catching Freedom
FRIDAY RACE 10 DOUBLE:
$10 - 13 / 11,13 = $20
OAKS EXACTA:
$10 EX BOX 11,13 = $20
OAKS - DERBY DOUBLE:
$8 11,13 / 2 = $16
$6 11,13 / 4 = $12
$6 11,13 / 11 = $12
$4 11,13 / 15 = $8
$10 11,13 / 17 = $20
OAKS - TURF - DERBY PICK 3:
$4 11,13 / 5,9,11 / 17 = $24
$2 11,13 / 5,9,11 / 2,4,11,15 = $48
Churchill Downs All Dirt Pick 5 (Saturday Race 4):
$0.50 6,7,8 / 10 / 5,7,11,12 / 6,9,11 / 2,4,11,15,17 = $90
TURF / DERBY DOUBLE (RACE 11):
$5 5,11 / 2,4,11 = $30
$3 9 / 2,4,11 = $9
$3 5,11 / 15 = $6
$2 9 / 15 = $2
KENTUCKY DERBY EXACTA:
$5 2,11,17 / 4 = $15
$3 KEY BOX 15 / 2,4,11,17 = $24
KENTUCKY DERBY TRIFECTA:
$1 4,15 / 4,15 / 2,3,6,7,8,11,14,17,18,19,20 = $22
$1 4,15 / 2,3,6,7,8,11,14,17,18,19,20 / 4,15 = $22
$1 2,3,6,7,8,11,17,18,19,20 / 4,15 / 4,15 = $22
$1 2,8,11,17 / 4 / 2,3,7,11,15,17,18 = $24
$1 2,8,11,17 / 2,3,7,11,15,17,18 / 4 = $24
$1,000 Wagering Strategy
Assumption - Want to take a big swing in the Kentucky Derby and have some multi race wagers for action along the way
Assumption - It’s the Derby, it happens once a year, take a swing and hope for the best. Looking for a chance at a five figure score.
2 DAY $1 PICK 6 (Friday - Race 5 - Will be separate listing on ADW)
$1 4,6 / 11,13 / 10 / 6,9,11 / 5,9,11 / 2,4,8,11,15,17 = $216
SHOW PARLAY (START WITH $30)
*Bet half of the starting amount, and roll all winnings into next show bet
Friday Race 5: 6 Xigera
Friday Race 11: 13 Just F Y I
Saturday Race 6: 10 Vahva
Saturday Race 9: 5 Legend of Time
Saturday Race 11: 5 Program Trading
Saturday Race 12: 4 Catching Freedom
FRIDAY RACE 8 PICK 4:
$1 2,5,6,7,9 / 7 / 4,6,9,13 / 11,13 = $40
$0.50 2,5,6,7,9 / 2 / 4,6,9,13 / 11,13 = $20
FRIDAY RACE 10 DOUBLE:
$10 - 13 / 11,13 = $20
OAKS EXACTA:
$15 EX BOX 11,13 = $30
OAKS - DERBY DOUBLE:
$10 11,13 / 2 = $20
$6 11,13 / 4,8,11 = $36
$5 11,13 / 15 = $10
$20 11,13 / 17 = $40
OAKS - TURF - DERBY PICK 3:
$5 11,13 / 5,9,11 / 17 = $30
$3 11,13 / 5,9,11 / 2,4 = $36
$1 11,13 / 5,9,11 / 8,11,15 = $18
Churchill Downs All Dirt Pick 5 (Saturday Race 4):
$0.50 6,7,8 / 10 / 5,7,11,12 / 6,9,11 / 2,4,11,15,17 = $90
DERBY CITY DISTAFF RACE 6:
$10 EXACTA 10 / 4 = $10
$1 TRIFECTA 10 / 1,3,7,8,9 / 4 = $5
TURF / DERBY DOUBLE (RACE 11):
$5 5,11 / 2,4,11 = $30
$3 9 / 2,4,11 = $9
$4 5,11 / 15 = $8
$2 9 / 15 = $2
KENTUCKY DERBY EXACTA:
$10 KEY BOX 2,11,17 / 4 = $60
$3 KEY BOX 15 / 2,4,11,17 = $24
KENTUCKY DERBY TRIFECTA:
$1 4,15 / 4,15 / 2,3,6,7,8,11,14,17,18,19,20 = $22
$1 4,15 / 2,3,6,7,8,11,14,17,18,19,20 / 4,15 = $22
$1 2,3,6,7,8,11,17,18,19,20 / 4,15 / 4,15 = $22
$1 2,8,11,17 / 4 / 2,3,7,11,15,17,18 = $24
$1 2,8,11,17 / 2,3,7,11,15,17,18 / 4 = $24
KENTUCKY DERBY SUPERFECTA:
$1 2,17 / 4 / ALL / 15 = $34
$1 2,17 / ALL / 4 / 15 = $34
$1 4 / 2,17 / ALL / 15 = $34