ITM Plus - Kentucky Oaks and Derby Wagering Strategy

For Budgets of $250 - $500 - $1,000

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*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 pretty much the only domestic race that will feature 20 runners. As a result, the payoffs can be huge but 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.

And 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 Thursday, 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 in accordance with the strength of your opinion.

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.

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 Diving Rod was going to 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:

To me, the Oaks is pretty straightforward. I like Malathaat and Travel Column and I’m splitting hairs if forced to pick one on top. I think both horses will be more than fine at the distance and are very likely to take a step forward.

As I said before, this race seems formful but Will’s Secret probably offers the most value of any runner. She’s eligible to improve with the added distance and should like the longer stretch of CD and the pace scenario relative to the Ashland.

Old Forrester Turf Classic:

Colonel Liam has done nothing wrong in 2021 and will be formidable. But he doesn’t tower over this field. I like Digital Age to repeat in this spot and think there’s an outside shot that Smooth Like Straight could wire the field. I’ll use them both as A’s and backup with Colonel Liam, Ivar, and “the other Chad”.

Kentucky Derby:

I have few knocks on the favorite, Essential Quality. He’s the fastest coming in (Thoro-Graph) and things appear to have gone according to plan all year long. It’s my opinion that those who are against this horse based on the Bluegrass Stakes are simply underrating Highly Motivated, and that’s likely to be a mistake on Saturday. It’s hard for me to see Essential Quality not “running his race” in the Kentucky Derby.

All that to say, he doesn’t have to win. The Breeders’ Cup Juvenile exacta paid $300 last year when Hot Rod Charlie finished second at 94-1. A repeat seems far from impossible but the reward will be far less - unless Hot Rod Charlie can turn the tables, and I happen to believe he can.

In general, I’m high on the Louisiana Derby. Historically, that’s not been the winning path for the Kentucky Derby but I like the first two finishers in this year’s edition quite a bit. Midnight Bourbon feels like the right underneath key although Mike Smith in irons ensures a wide trip and probably strips some of the value. The other one I think makes sense underneath is Dynamic One who I like on breeding, has been working well, and he was clearly best in the Wood.

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. At the same time, I’m having a hard time fully eliminating horses as the second half of the field seem a bit interchangeable except for running style.

Most Likely: Hot Rod Charlie, Essential Quality

Next Best: Highly Motivated, Medina Spirit, Known Agenda, Rock Your World (probably the weakest of this bunch in my opinion - feels like a Win or Out type and I’m only really using defensively)

Value and Underneath Keys: Midnight Bourbon, Dynamic One,

No Real Opinion: Mandaloun, O Besos, King Fury, Sainthood, Super Stock, Helium, Keepmeinmind

Against: Like the King, Soup and Sandwich, Hidden Stash, Brooklyn Strong, Bourbonic

$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.

OAKS SUPERFECTA:

$1 6,10 / 6,10 / 11 / 1,3,4,5,8,9,12,14 = $16

$1 6,10 / 1,3,4,5,8,9,12,14 / 11 / 6,10 = $16

$1 1,3,4,5,8,9,12,14 / 6,10 / 11 / 6,10 = $16

$1 6,10 / 6,10 / 1,3,4,5,8,9,12,14 / 11 = $16

$1 6,10 / 1,3,4,5,8,9,12,14 / 6,10 / 11 = $16

$1 1,3,4,5,8,9,12,14 / 6,10 / 6,10 / 11 = $16

OAKS EXACTA:

$2 6,10 / 11 = $4

OAKS - DERBY DOUBLE:

$10 6,10 / 9 = $20

$5 3,4,12 / 9 = $15

$5 6,10,12 / 14 = $15

KENTUCKY DERBY EXACTA:

$5 9 / 1,8,14,15,17 = $25

$2 9 / 10,11 = $4

$5 1,8,14,15,17 / 9 = $25

$2 10,11 / 9 = $4

KENTUCKY DERBY WIN PLACE SHOW:

$14 - 9 = $42

$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 SUPERFECTA:

$1 6,10 / 6,10 / 11 / 1,3,4,5,8,9,12,14 = $16

$1 6,10 / 1,3,4,5,8,9,12,14 / 11 / 6,10 = $16

$1 1,3,4,5,8,9,12,14 / 6,10 / 11 / 6,10 = $16

$1 6,10 / 6,10 / 1,3,4,5,8,9,12,14 / 11 = $16

$1 6,10 / 1,3,4,5,8,9,12,14 / 6,10 / 11 = $16

$1 1,3,4,5,8,9,12,14 / 6,10 / 6,10 / 11 = $16

OAKS EXACTA:

$2 6,10 / 11 = $4

OAKS - DERBY DOUBLE:

$20 6,10 / 9 = $40

$5 3,4,12 / 9 = $15

$10 6,10,12 / 14 = $30

OAKS - TURF - DERBY PICK 3:

$11 6,10 / 6,7 / 9,14 = $88

$2 3,4,12 / 6,7 / 9,14 = $24

$3 6,10 / 3,5 / 9,14 = $24

$1 6,10 / 6,7 / 1,8,11,17 = $16

$2 3,4,12 / 3,5 / 9,14 = $24

KENTUCKY DERBY TRIFECTA:

$2 9,14 / 9, 14 / 1,7,8,10,11,15,16,17 = $32

$1 9,14 / 1,7,8,10,11,15,16,17 / 9,14 = $16

$1 1,7,8,10,11,15,16,17 / 9,14 / 9,14 = $16

KENTUCKY DERBY WIN PLACE SHOW:

$25 - 9 = $75

$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.

One quick note. Originally, I’d have planned to tackle the Pick 5 that ends in the Kentucky Derby but even with a $1,000 bankroll, I feel undercapitalized (see above). I’ll avoid that sequence and take a stab at the Two Day Pick 6 which seems more manageable or at least involves races where I have stronger opinions.

2 DAY $2 PICK 6 (Friday - Race 8)

$2 2,3 / 6,10 / 4 / 2,4,12 / 3,4,5,6,7 / 9,14 = $240

OAKS SUPERFECTA:

$1 6,10 / 6,10 / 11 / 1,3,4,5,8,9,12,14 = $16

$1 6,10 / 1,3,4,5,8,9,12,14 / 11 / 6,10 = $16

$1 1,3,4,5,8,9,12,14 / 6,10 / 11 / 6,10 = $16

$1 6,10 / 6,10 / 1,3,4,5,8,9,12,14 / 11 = $16

$1 6,10 / 1,3,4,5,8,9,12,14 / 6,10 / 11 = $16

$1 1,3,4,5,8,9,12,14 / 6,10 / 6,10 / 11 = $16

OAKS EXACTA:

$8 6,10 / 11 = $16

OAKS - TURF - DERBY PICK 3:

$12 6,10 / 6,7 / 9,14 = $96

$2 3,4,12 / 6,7 / 9,14 = $24

$3 6,10 / 3,4,5 / 9,14 = $36

$1 6,10 / 6,7 / 1,8,11,17 = $16

$2 3,4,12 / 3,4,5 / 9,14 = $36

KENTUCKY DERBY SUPERFECTA:

*I was really torn here on the underneath key. I sided with Midnight Bourbon over Dynamic One - tough call and one I hope I don’t regret.

$1 9,14 / 9,14 / 10 / 1,4,5,6,7,8,11,12,15,16,17,18 = $24

$1 9,14 / 1,4,5,6,7,8,11,12,15,16,17,18 / 10 / 9,14 = $24

$1 1,4,5,6,7,8,11,12,15,16,17,18 / 9,14 / 10 / 9,14 = $24

$1 9,14 / 9,14 / 1,4,5,6,7,8,11,12,15,16,17,18 / 10 = $24

$1 9,14 / 1,4,5,6,7,8,11,12,15,16,17,18 / 9,14 / 10 = $24

$1 1,4,5,6,7,8,11,12,15,16,17,18 / 9,14 / 9,14 / 10 = $24

KENTUCKY DERBY TRIFECTA:

$4 9,14 / 9, 14 / 1,7,8,10,11,15,16,17 = $64

$2 9,14 / 1,7,8,10,11,15,16,17 / 9,14 = $32

$2 1,7,8,10,11,15,16,17 / 9,14 / 9,14 = $32

$1 1,8,17 / 9,14 / 1,7,8,9,10,11,14,15,16,17 = $48

$1 1,8,17 / 1,7,8,9,10,11,14,15,16,17 / 9,14 = $48

KENTUCKY DERBY EXACTA:

$6 9 / 1,8,14,15,17 = $30

$3 9 / 10,11 = $6

$6 1,8,14,15,17 / 9 = $30

$3 10,11 / 9 = $6