2022 Kentucky Oaks and Derby Wagering Strategies
$250, $500 and $1,000 Budgets
*Note - This is long but hopefully worth your time. I welcome your feedback in the comments. Thanks - Tyler
Ticket construction and overall wagering strategy are topics that clearly deserve more attention. However, the appropriate wagering strategy is largely dependent on one’s budget and goals. The number of iterations is limitless and as a result, it’s a topic that most pundits mostly ignore.
Most of the current talk (primarily on social media) on the subject comes as harsh criticism as opposed to constructive feedback. That is, the keyboard warriors assume they know what’s best for you despite having no knowledge of 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 actually welcome it.
My plan here is to cover a few different budgets for the Kentucky Oaks and Kentucky Derby cards. We will outline approaches for budgets of $250, $500, and $1,000.
In order to understand my wagering strategy, it’s necessary that I explain my handicapping opinions so you can see how I plan to leverage them at the windows. You may disagree with my handicapping but might be able to gain some insights as to how I think through my approach. Put differently, the idea here isn’t that you tail my suggestions, but that you take your opinions and hopefully, think about the best way to spend your budget.
Before I jump in, I want to provide a couple of generalities with regard to 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. 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 biggest days the sport has to offer.
But it’s unlikely that your opinion is equally strong in all of the 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 spend some time figuring 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 was going to 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, a balanced approach using the last two concepts is generally my strategy for these big days.
My Handicapping Assessment
Again, in order for the wagering strategy to make sense, I need to explain where I stand from a handicapping standpoint.
Kentucky Oaks:
The weather…Ugh.
Echo Zulu might have a relative pace advantage but she comes in slower than a few and even Asmussen has questioned her ability to get the distance. Secret Oath earned the right to take on the colts and didn’t disgrace herself. The rider change likely helps but I’m afraid she might be tailing off and would need a lifetime best in here.
That leaves Nest and Kathleen O. I prefer Nest and she’s likely my strongest opinion of the weekend. I’ll press her.
Last year, I keyed Will’s Secret underneath and that proved to be a good decision. This year, I think Shahama could serve that role. She’s new to the Pletcher barn but she appears to be training quite well. She needs to improve but has the pedigree (half-sister to Lookin at Lucky) and trainer that makes it possible. This filly broke slowly in her past two starts (not ideal) and she might not have beat anything but she looks push button to me. I’m hoping Flavien Prat can get her away cleanly and she can hit the board. Admittedly, I was hoping for more than 15-1.
Here’s how I saw the rest of the field:
Turf Classic:
The top choices on the morning line appear to be best at a mile. I think there’s a chance to look for value in this spot. There’s also a good chance the ML is just wrong.
Adhamo (IRE) got a massive setup in his US debut but couldn’t get the job done owing to a very wide trip. A Chad Brown-Flavien Prat Double into the Kentucky Derby looks more than possible.
I will likely backup with Santin who has disappointed as the favorite in his past two. I’m willing to give him another shot here.
Kentucky Derby:
My typical approach in the Kentucky Derby is to assess the runners based on speed figures and then make an assessment of 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.
This year, Zandon is the horse that appears most likely to run his race. I can’t argue if you suggest it’s Epicenter, but the reality is he doesn’t possess the speed figures that would necessarily support favoritism. That said, he should theoretically be ensured a more favorable trip. Nonetheless, Zandon is my definite key in the Kentucky Derby.
I also think Messier is a very dangerous horse. I will not be surprised if he’s right off the flank or potentially in front of Summer Is Tomorrow. Brian Lynch has hinted at rating Classic Causeway which means we are one misstep by Summer Is Tomorrow from Messier setting the pace. Ultimately, he might be the most likely winner of the race.
Finally, I’m not backing down from my support of Crown Pride (JPN). I do think he has a big shot to win the race and certainly feel like he’s a must-use in all vertical slots. While others will try to get Barber Road or Simplification in the picture, I’ll toss them and use the Japanese invader.
I view Taiba as a bit of an all-or-nothing type. He either wins or finishes nowhere in my opinion.
I’m not really opposing any of the logical contenders. They seem most likely to fire and all of them are in the hands of very capable trainers. The chart below lays out how I see the contenders.
$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.
KENTUCKY OAKS WIN PLACE SHOW:
$6 - 13 = $30
OAKS TRIFECTA:
$1 4 / ALL / 13 = $12
$1 4 / 13 / All = $12
$0.50 1,2,3,10 / 4,13 / 4,13 = $4
$0.50 13 / 4 / ALL = $6
$0.50 13 / ALL / 4 = $6
OAKS EXACTA:
$2 KEY BOX 4 / 1,2,3,13 = $16
OAKS - DERBY DOUBLE:
$10 4 / 6,10 = $20
$4 4 / 7 = $6
$5 13 / 6,10 = $10
$2 13 / 7 = $2
KENTUCKY DERBY EXACTA:
$5 KEY BOX 7 / 6,10 = $20
$5 KEY BOX 10 / 1,3,6,7 = $40
$2 KEY BOX 10 / 8,16,19 = $12
KENTUCKY DERBY TRIFECTA:
$0.50 6,7,10 / 6,7,10 / 1,3,5,6,7,8,10,13,15,16,19 = $30
$1 12 / 6,7,10 / 6,7,10 = $6
KENTUCKY DERBY WIN PLACE SHOW:
$10 - 7 = $30
$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
OAKS TRIFECTA:
$2 4 / ALL / 13 = $24
$2 4 / 13 / All = $24
$1 1,2,3,10 / 4,13 / 4,13 = $8
$1 13 / 4 / ALL = $12
$1 13 / ALL / 4 = $12
OAKS EXACTA:
$2 KEY BOX 4 / 1,2,3,13 = $16
OAKS - DERBY DOUBLE:
$20 4 / 6,10 = $40
$8 4 / 7 = $8
$8 13 / 6,10 = $16
$4 13 / 7 = $4
American Turf Stakes (Saturday Race 9) Pick 4:
$0.50 5,6,7,9 / 3,6 / 3,7,8,10 / 1,3,6,7,10,12 = $96
Churchill Downs Stakes (Saturday Race 10) Pick 3:
$5 3,6 / 8 / 6,7,10 = $30
$2 3,6 / 3,7,10 / 6,7,10 = $36
KENTUCKY DERBY EXACTA:
$5 KEY BOX 7 / 6,10 = $20
$5 KEY BOX 10 / 1,3,6,7 = $40
$2 KEY BOX 10 / 8,16,19 = $12
KENTUCKY DERBY TRIFECTA:
$1 6,7,10 / 6,7,10 / 1,3,5,6,7,8,10,13,15,16,19 = $60
$2 12 / 6,7,10 / 6,7,10 = $12
KENTUCKY DERBY WIN PLACE SHOW:
$10 - 7 = $30 (Odds of 15-1 or higher)
$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.
***Typically, I’d try to attack the Kentucky Derby Superfecta but too many horses are interchangeable this year. I like 3-5 horses to win and can’t eliminate enough to make this a viable strategy. I’m avoiding this year.
2 DAY $2 PICK 6 (Friday - Race 6 - Will be separate listing on ADW)
$2 2 / 4,10,13 / 2,4,5,6 / 3,6 / 8 / 1,6,7,10,12 = $240
OAKS TRIFECTA:
$2 4 / ALL / 13 = $24
$2 4 / 13 / All = $24
$1 1,2,3,10 / 4,13 / 4,13 = $8
$1 13 / 4 / ALL = $12
$1 13 / ALL / 4 = $12
OAKS EXACTA:
$5 KEY BOX 4 / 1,2,3,13 = $40
$10 BOX 4,13 = $20
OAKS - DERBY DOUBLE:
$20 4 / 6,10 = $40
$10 4 / 7 = $10
$8 13 / 6,10 = $16
$4 13 / 7 = $4
American Turf Stakes (Saturday Race 9) Pick 4:
$0.50 5,6,7,9 / 3,6 / 3,7,8,10 / 1,3,6,7,10,12 = $96
$1 5,6,7,9 / 3,6 / 8 / 6,7,10 = $24
Churchill Downs Stakes (Saturday Race 10) Pick 3:
$10 3,6 / 8 / 6,7,10 = $60
$4 3,6 / 3,7,10 / 6,7,10 = $72
KENTUCKY DERBY EXACTA:
$10 KEY BOX 7 / 6,10 = $40
$10 KEY BOX 10 / 1,3,6,7 = $80
$4 KEY BOX 10 / 8,16,19 = $16
$5 12 / 6,7,10 = $15
KENTUCKY DERBY TRIFECTA:
$1 6,7,10 / 6,7,10 / 1,3,5,6,7,8,10,13,15,16,19 = $60
$2 12 / 6,7,10 / 6,7,10 = $12
KENTUCKY DERBY WIN PLACE SHOW:
$25 - 7 = $75 (Odds of 15-1 or higher)