*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 deserve more attention. However, the appropriate wagering strategy largely depends 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 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.
I plan 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.
To understand my wagering strategy, I must 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 insights into 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 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, I need to explain where I stand from a handicapping standpoint.
Kentucky Oaks:
First off, I hope the weather cooperates.
I find it hard to be against Wet Paint. Based on the ThoroPACE Forecast, she figures to get the best pace setup she’s seen to date. She drew fine and while she will need to work out a trip, she looks reliable.
I do think Botanical should enjoy the dirt. And possibly move up on the surface. She’s training well and while I don’t fully trust Chris Landeros - She’s my top pick.
The value of the race, in my opinion, is Gambling Girl. She’s been up against it pace wise in her last two starts. I think she’ll handle the distance just fine and she might be the key to enhanced exotic payouts.
In terms of other horses I’d consider including: Defining Purpose, The Alys Look, Southlawn and Pretty Mischeivous.
American Turf:
What a race this is. I am not squarely against Major Dude, but he does figure to be an underlay in this spot. He’s garnered much attention for more than holding his own with his Derby-bound workmate, Kingsbarns. Again, he could take this, but he’s too short for me.
Far Bridge and Carl Spackler look like serious animals. Both should be respected. But the horse I’m interested in keying is Talk of the Nation. He might not hold at 10-1, but he gets a solid rider upgrade (for this track) and looks formidable based on his pair of turf efforts. His tactical speed and draw should allow him to trip out in this spot.
Turf Classic:
Assuming this field stays intact, there is plenty of pace signed on.
Up to the Mark was certainly up against it last month at Keeneland. The pace was slow and the course was playing favorably to speed throughout the meet. Double whammy. He’s been a bit of a revelation since switching to grass and while the connections are likely hoping to win the next race, they’re in with a big shot here.
Another horse hoping for a brisk pace is Hong Kong Harry. Prat opts to go here for a barn that, based on the results from Keeneland, has figured out how to ship to Kentucky.
Kentucky Derby:
***The analysis below fully accounts for Cyclone Mischief (who strengthens my conviction on everyone but Verifying) but not Mandarin Hero. I will not use him on the win end but I don’t know if I want to change some of the exotics. If I do, I’ll send an update. I wanted to get this out and not delay…
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.
Angel of Empire is the horse that appears most likely to run his race this year. If forced to pick a single horse, he’d be my selection.
Candidly, I’m struggling to narrow the field on the win end. I don’t like that, but I also can’t do much about it now.
Part of the reason I’m struggling to toss horses from the win slot is that I like two long shots underneath. I’ve stated my case in various ways over the two weeks. I think Sun Thunder and Disarm will get the setup they’ll need to pass horses - something they haven’t gotten in their most recent starts. If one of them is in the Trifecta, I don’t want to miss the race just because I don’t ‘love’ Forte.
In the event I’m wrong on them Two Phil’s and Skinner are two colts with big shots at odds over 15-1.
Last year I made an argument for Crown Pride (JPN). I didn’t see him being part of the meltdown, and he faded. I’m not letting that color my opinion of Derma Sotogake (JPN). He seems quirky for sure, but he has loads of talent and versatility. Lemaire should have options from the outside post, and he has a huge shot. But what will his odds be? I’ve been pretty vocal that I think he’s 10-1+, but some sharp folks suggest he will be way lower. I’m not sure. And honestly, it doesn’t matter in this setting. If Derma Sotogake goes off at 6-1 and finishes second to Angel of Empire, it still figures to be an exacta of $75-1 or more. I’m not going to quibble with that.
In summary, I’m not opposing any of the logical contenders other than Practical Move. They seem 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.
Churchill Downs Race 14:
Everso Mischievous worked heads up with Verifying over the weekend. Immediately upon seeing that, I knew he’d be entered in the nightcap on Derby Day. Brad Cox unleashed Strobe last year in this exact spot. While this race came up a little tougher than I expected, I think he’s a solid single.
***Note, even with $1,000 I’d feel undercapitalized for the Pick 5 or Pick 6 that ends in the Kentucky Derby. The Turf Sprint and Pat Day Mile make that sequence unapproachable based on my handicapping opinions.
$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.
FRIDAY RACE 10 DOUBLE:
$5 - 11 / 6,7 = $10
$3 - 10 / 6,7 = $6
OAKS TRIFECTA:
$1 6,7 / 2,4,6,7,10,11,14 / 3 = $12
$0.50 2,4,6,7,10,11,14 / 6,7 / 3 = $6
$1 6,7 / 3 / 2,4,6,7,10,11,14 = $12
$0.50 2,4,6,7,10,11,14 / 3 / 6,7 = $6
OAKS EXACTA:
$2 KEY BOX 6,7 / 3 = $8
OAKS - DERBY DOUBLE:
$5 6,7 / 3, 14, 17 = $30
$3 6,7 / 2, 9, 13 = $18
KENTUCKY DERBY EXACTA:
$5 BOX 3,14,17 = $30
$2 BOX 3,13,14,17 = $24
KENTUCKY DERBY TRIFECTA:
$0.50 14 / 2,3,5,9,11,13,15,17 / 11,13 = $7
$0.50 2,3,5,9,11,13,15,17 / 14 / 11,13 = $7
$0.50 3,14,17 / 3,14,17 / 2,3,5,9,11,13,14,15,17 = $21
$0.50 5,15 / 3,14,17 / 2,3,5,9,11,13,14,15,17 = $21
$0.50 3,14,17 / 5,15 / 2,3,5,9,11,13,14,15,17 = $21
KENTUCKY DERBY WIN PLACE:
$5 - 14 = $10
$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
FRIDAY RACE 10 DOUBLE:
$10 - 11 / 6,7 = $20
$5 - 10 / 6,7 = $10
OAKS TRIFECTA:
$1 6,7 / 2,4,6,7,10,11,14 / 3 = $12
$0.50 2,4,6,7,10,11,14 / 6,7 / 3 = $6
$1 6,7 / 3 / 2,4,6,7,10,11,14 = $12
$0.50 2,4,6,7,10,11,14 / 3 / 6,7 = $6
OAKS EXACTA:
$5 KEY BOX 6,7 / 3 = $20
OAKS - DERBY DOUBLE:
$10 6,7 / 3, 14, 17 = $60
$5 6,7 / 2, 9, 13 = $30
$3 3, 4, 11, 14 / 3, 14, 17 = $36
$2 3, 4, 11, 14 / 2, 9, 13 = $24
Churchill Downs Stakes (Saturday Race 10) Pick 3:
$3 7 / 5,7,8,9 / 3,14,17 = $36
$1 4 / 5,7,8,9 / 3,14,17 = $12
$2 7 / 5,7,8,9 / 2, 9, 13 = $24
$0.50 4 / 5,7,8,9 / 2, 9, 13 = $6
KENTUCKY DERBY EXACTA:
$5 BOX 3,14,17 = $30
$2 BOX 3,13,14,17 = $24
$5 14 / 5,15 = $10
$4 14 / 2,9,11 = $12
KENTUCKY DERBY TRIFECTA:
$1 14 / 2,3,5,9,11,13,15,17 / 11,13 = $14
$1 2,3,5,9,11,13,15,17 / 14 / 11,13 = $14
$1 3,14,17 / 3,14,17 / 2,3,5,9,11,13,14,15,17 = $42
$0.50 5,15 / 3,14,17 / 2,3,5,9,11,13,14,15,17 = $21
$0.50 3,14,17 / 5,15 / 2,3,5,9,11,13,14,15,17 = $21
$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 9 - Will be separate listing on ADW)
$1 4,10 / 6,7 / 2 / 4,7 / 5,7,8,9 / 2,3,5,9,14,15,17 = $224
$1 4,10 / 6,7 / 5 / 4,7 / 5,7,8,9 / 3,14,17 = $96
FRIDAY RACE 10 DOUBLE:
$10 - 11 / 6,7 = $20
$5 - 10 / 6,7 = $10
OAKS TRIFECTA:
$1 6,7 / 2,4,6,7,10,11,14 / 3 = $12
$0.50 2,4,6,7,10,11,14 / 6,7 / 3 = $6
$1 6,7 / 3 / 2,4,6,7,10,11,14 = $12
$0.50 2,4,6,7,10,11,14 / 3 / 6,7 = $6
OAKS EXACTA:
$5 KEY BOX 6,7 / 3 = $20
OAKS - DERBY DOUBLE:
$10 6,7 / 3, 14, 17 = $60
$5 6,7 / 2, 9, 13 = $30
$3 3, 4, 11, 14 / 3, 14, 17 = $36
$2 3, 4, 11, 14 / 2, 9, 13 = $24
Churchill Downs Stakes (Saturday Race 10) Pick 3:
$3 4 / 5,7,8,9 / 3,14,17 = $36
$1 4 / 5,7,8,9 / 2, 9, 13 = $12
Churchill Downs Stakes (Saturday Race 10) Pick 5:
7 / 5,7,8,9 / 2,3,5,9,13,14,15,17 / 2,3,5,6,8,9,10 / 2 = $112
4 / 5,7,8,9 / 3,14,17 / 2,3,5,6,8,9,10 / 2 = $42
KENTUCKY DERBY EXACTA:
$5 BOX 3,14,17 = $30
$2 BOX 3,13,14,17 = $24
$5 14 / 5,15 = $10
$4 14 / 2,9,11 = $12
KENTUCKY DERBY TRIFECTA:
$1 14 / 2,3,5,9,11,13,15,17 / 11,13 = $14
$1 2,3,5,9,11,13,15,17 / 14 / 11,13 = $14
$1 3,14,17 / 3,14,17 / 2,3,5,9,11,13,14,15,17 = $42
$0.50 5,15 / 3,14,17 / 2,3,5,9,11,13,14,15,17 = $21
$0.50 3,14,17 / 5,15 / 2,3,5,9,11,13,14,15,17 = $21
KENTUCKY DERBY WIN PLACE:
$25 - 14 (At 6-1 or higher) = $50