6 Ways to Think Like a Winning Handicapper

By Ray Wallin

Winning handicappers who consistently make a profit playing the races have different thinking behaviors than the casual player. Some may be part-time horseplayers while others may make their living playing the races. But what exactly sets them apart from the average handicapper?

Over the course of the last 30-plus years I have gotten to know a lot of successful handicappers. Some were young and some were old. Others dressed impeccably and others looked like they were homeless. Some hung out in the Clubhouse and others with the rest of the degenerates out on the Grandstand apron at Monmouth Park. They all played a little differently. A guy I knew named Monty was strictly a horizontal player, while “Jimmy Legs” would craft exactas and trifectas in the most efficient manner I have ever seen.

I had the good fortune to pick their brains, not only about angles and figures, but how they mentally approach, analyze, and digest a race. While they all seemed so different on the surface, they did have one thing in common, the way they thought about the races they were handicapping.

1. Accuracy

Guys like my late Uncle Dutch kept amazing stats on trainers and jockeys before they became common place in the past performances. “Jimmy Legs” could rattle off how every local trainer performed under different conditions on the turf, and if he didn’t know a trainer that was shipping in, he “had a guy” that knew the same information he did at that other track. “Lenny Figures” would look for a particular combination or discrepancy in his pace figures to find his plays. When you saw him heading to the windows, you knew he more than likely was there to cash a ticket.

By knowing the facts and having the research to back it up you can make confident and well-informed wagers. Winning handicappers know when the cards are stacked in their favor and when to exploit them based on constantly checking the performance of their data.

2. Significance 

What is important to the race you’re handicapping? The horse you are considering has an impeccable pedigree that makes the rest of the field look like cart horses. You love Tapit colts, they are bred to run for days.

But does this piece of information have any significance to the conditions of today’s race? If today’s race is a maiden special weight race full of first time starters at Saratoga the answer is different than if it is a field of older horses running in a conditioned $4,000 claimer for non-winners of a race in the last year at Mountaineer.

Not all information should be weighted the same under different conditions. Winning handicappers know what information is relevant for the conditions of the race they are handicapping.

3. Depth

I know good handicappers that pick their contenders and make a profit. I know great handicappers that pick their contenders and then try to poke holes in their own handicapping.

One afternoon I was at the track with Tunnel-Vision Tony. Tony was a good handicapper. He had a mental checklist he followed, he watched replays and took trip notes, and he kept great records so he could test his thinking. He would handicap a race and use his contenders to craft a ticket. When we would compare our thoughts, he would joke that I was often trying to talk myself out of playing a race. There was nothing farther from the truth.

After I handicap a race and decide that it is going to be playable, I do a premortem as a final check against my thinking. I try to find what I think could go wrong before the race is run to gauge the level of risk I think there is playing the race. If I think the race is too risky of a proposition I either add more contenders or pass the race.

Winning handicappers know when they may have discounted a factor or a potential pace scenario. They know how to balance their wagering against the risk.

4. Breadth

I spent many nights of my life on the second floor of the old Meadowlands grandstand. One regular, The Schnoz, was notorious for only using the most likely way he saw a race setting up as his way of selecting contenders. He generally would do well, but if there was any change to the early pace he’d be tearing up his tickets shortly thereafter.

Any time I assess the pace of the race I ask myself a couple of “what-if” questions. What if my early speed horse gets pressured instead of getting loose on the lead? Will he fold or will he last? What if the early fractions are forced to be a little faster than my contenders are comfortable with? Do they have a versatile running style or will they be unable to handle it?

Winning handicappers consider other points of view, especially when it comes to pace scenarios. A bad break from the gate or some early traffic is enough to change the dynamics of the pace.

5. Logic

Successful handicappers are an interesting bunch. While they may seem unapproachable, many of them love to talk about horse racing and handicapping. Many of them are also willing to talk about how they came up with their contenders or plays for a particular race.

Our old track friend The Marine would makes his picks based on what track the race was at and what the distance of the race was. He was basing this on what happened on a handful of occasions he remembered a nice priced horse winning under those conditions. Does this sound very logical?

Winning handicappers have a logical explanation for how they arrived at their plays. It could be pedigree, workout patterns, or trainers for first time starters or how they dissected the pace of the race.

6. Fairness

How many times have you handicapped a race and think that your horse can’t lose? He is a solid standout in class, speed, pace, and form. There is no way he can lose today – until he does. He plodded home before the next race started. When you saw him in the paddock he looked a bit gimpy, but he was tight and would loosen up on the track before getting in the gate, right?

Wrong. You were set on this horse based on how you handicapped the race on paper. You found every excuse for why he would run amazingly despite what your eyes showed you.

Winning handicappers do not ignore facts that disagree with their thinking. If they see their sure thing looking gimpy in the paddock or being fractious, they know to pass on the race and wait for their next good betting opportunity.

Through all my years of playing the races I have met winners, losers, and everything in between. Yet those that win consistently think a little differently. By changing the way you think, you too can make a profit at the track.