Betting Strategy: Schooled by The Masters

Profile Picture: Kevin Kilroy

May 28th, 2022

In honor of getting through the first six legs of Betting Strategies, I took the week to read back through some of the best handicapping books on my shelf. My hope was to uncover some gems directly dealing with multi-race wagers. I flipped through many, but Beyer On Speed and The Winning Horseplayer, both by Andrew Beyer, and Betting Thoroughbreds by Steven Davidowitz caused me to circle the wagons.

As I read, again and again, their words dealing with betting discipline, consistent strategy, and fattening up my ticket structure felt like tough-love slaps across my face. These areas caught my attention because they are the betting strategy weaknesses I need to address. If the reason we return to the masters is to be humbled, then I succeeded and have the pie to show for it. 

More often than not, books on handicapping Thoroughbreds include a section on betting strategy at the back. Maybe as an appendix, sometimes just a topic glossed over and included as filler. Handicapping itself, picking winners, being right when someone asks “Kilroy, who you like in the first?” has been the focus of my education. So maybe I was reading some of this advice for the first time, but in the words of another master, Mr. Miyagi might point out: one only hears when one is ready to listen.

Here are a few of the gems that hit home for me:

“If the typical handicapper has one fatal flaw, it is that he has no consistent betting strategy and makes no effort to formulate one.” - Andrew Beyer, The Winning Horseplayer

I take consistent betting strategy to mean developing a system that is adhered to with discipline. A methodology. Knowing what you do successfully and committing to playing that angle or exploiting that situation whenever it arises.

Calling back to previous Betting Strategy interviews, Paul Sengal Jr. spoke about his “best speed figure off a layoff” angle, and Chad Schexnayder discussed his using all on big field turf legs when next to his strong dirt race opinions.

This shifts our definition of success: when you make one bet on one race, it should not be judged as successful or unsuccessful solely based on that one outcome--win or lose. Each bet is an instance of a larger series of bets made for the same reason, spread out over a meet, or a quarter, or a year. Consistency. Because if the angle is good, then it will be profitable over time. Also, if we put our big thinking into developing the system, then we can avoid any day-to-day psychology of gambler hang-ups because we are administering a system, not riding the dopamine waves.

“The worst pick six bet is one larger than $8 and less than $64. Anyone is entitled to a lark of up to $8. A play of $64 on a very easy card is the minimum requirement for a fighting chance. Everything in between is too much to squander and too little to maneuver with.” - Beyer On Speed, where Beyer is quoting Steve Crist.

This undressed me to my drawers. I am guilty of this in my horizontals and in my verticals. I’ve been too skinny, too shrewd, too exacting for too long. At least, building skinny tickets has not played into my handicapping strengths, meaning I have not been cashing enough of these bets.

I can hear my friend James Godby now chastising me after my homerun hit just slices foul. “Did you box it?” “Hell no, I didn’t box it.” “Did you play a saver?” “Yeah, but not with the price horse I liked, just the logicals.”

Looking back at my tickets and recollecting many a tough loss, I see it clear as day. I have always loved this game for the ability to dream big--bet a little to win a lot; make a big score and quit my day job to write books and bet the ponies. And when sharp handicappers advise narrowing down your tickets, moving away from the box, weighting your tickets according to your opinion, I’ve heard them loud and clear and I do believe in that, but personally, I have not been able to be successful at it. I have spent years scoffing at playing all and boxing, and I have differentiated between horses I think can run first, second, third, fourth, or toss, building tickets where I lose if the price horse I liked runs second because I thought third was the best he could do. 

What I hear from this quote is I need to peel more off of my bankroll when I find situations I like instead of feeling over-confident in my opinions and therefore playing a skinny ticket. Not that I need to use all or box, but that I need to build a structure that ensures if I am right, I will get paid.

Even worse, calling back to the above quote about consistency, sometimes I do this structure and other times I do that. But for no known reason. A consistent betting strategy is not just playing the same angles. We also need to employ the same ticket structures when we play these angles--or more so, have a system of reasoning for why we structure this way in this situation and that way in another.

“Anybody who has ever played the pick six knows how difficult it is to survive six races without encountering at least one implausible, unforeseeable result. So, Crist said, ‘I try to give myself the chance to be wrong on one race if I can be right in enough other spots. If I am right four times, I want to give myself a good chance to win those other two races. And if I’m dead right on three races, I’ll use six or seven horses in a couple of the others and hope for something silly to happen.’” - Beyer On Speed, where Beyer is quoting Steve Crist.

I take that to mean loosening the filter for which horses come into your tickets. Allowing your selections to be evidence of thinking that does not directly reflect your typical handicapping angles. You can accomplish this through buying the leg, but how else can we open up our selection process to the horses that other tickets won’t have and the horses that our personal handicapping logic does not ever land on?

This is definitely a key skill to have in tournament play. Game theory shows us that the points we get with a horse that no other contest player has are worth more than the points we get from a horse a large group has because to win we are looking to differentiate from the group, not mingle with them. The same goes for exotic betting.

In Betting Thoroughbreds, Steven Davidowitz offers the advice of having three groups of horses: one key horse, your contenders, and two or three offering the lowest payoffs--meaning the ones the public has decided are most likely to win. With these three groups, you structure to cover the likely scenarios. When we are betting into blind pools as with multi-race wagers, we could substitute the ML favorites. Or we could go the other way and include the two or three horses that are not complete tosses but we don’t consider to be contenders. The horses that win and make us say well that was silly.

I love this quote because it does not tell us what to do but shows us the thinking that will help us land on the horses we need to differentiate our tickets from the majority. And we all know the majority is wrong ~66% of the time on win bets, much more than that in exotic pools.