Winning at Losing

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The emails arrived in my in-box about an hour apart, three days before the Kentucky Derby. One was about artificial intelligence to help handicap the race and the other was about applied sports psychology.

The former included “leveraged, prioritizing and assimilates” in one sentence. I stopped reading there. 

The latter offered an expert’s opinion on jockeys, specifically how they deal with pre- and post-race routines, confronting superstitions, controlling excitement, recovering from a bad race and dealing with defeat. I did not call the expert.

Who needs an expert? We are in the racing game, we are our own experts – routines, superstitions, excitement, recovering from bad races and dealing with defeat all day, every day. As one of my partners says every time we lose a race, “Sean, our best quality is our resiliency.” If you’re aren’t good at establishing routines, managing superstitions, tempering excitement, bouncing back from bad races and digesting defeat, well, you’re long gone.

A few thoughts on each…


When I was riding, I had a specific chair and corner in the jocks’ room, I liked to be there first, sometimes renovating the jocks’ room to meet our needs. I set my tack bag directly in front of my chair, saddles to my right, girths to my left, whips tucked next to the chair, helmet under the chair…I had a way of fastening rubber bands around my wrists, three tan ones around the cuffs of the silks, one black one around each white fingerless glove. None of this made the horses run faster but provided a hint of shelter from the storm for me. Everybody has their shelters.

I watched guys ride without any routines, Matt McCarron once walked in the jocks’ room at Camden and didn’t even look for a chair, he leaned on a cardboard trash can and got dressed, his tack still carrying mud from the week before, he won a couple of races that day. I still don’t know how he did it.


I didn’t have many tried and true ones – black cats, mirrors, rabbit’s foot, peanut shells in the shed row, nah, but there were things I said and didn’t say, there were things I did do and didn’t do, there were thoughts I tried to capture and thoughts I simply ignored. Superstitions? In a way, I guess.

And, oh yeah, I still won’t walk across a handicap space because Jonathan Kiser told me it was bad luck, so many years ago. Deep down, I don’t think it makes any difference but it does makes me wink at the sky and think of him, gone nearly 17 years now.

Controlling excitement.

As a jockey, this is easy, actually. You have so many bad days, so many disappointments that I found controlling the excitement simply part of the routine. Yes, you were excited to ride, excited for the opportunity on a good horse or the buzz of a big race, but, especially riding jumpers, excitement was always tempered with the realization of disaster. Not a problem.

Recovering from bad races.

Easier for flat riders than jump jockeys in this country, because they’re riding eight, nine races a day, five, six days a week, rather than a handful of rides once or twice a week like the jump jockey. They were long weeks after going 0-for-7 on the weekend. It’s easier to clean the slate when there’s a lot of writing. I struggled with this for most of my career, too emotional, too absorbed by the losses. In a way, the jockeys I rode with who weren’t taking it as seriously had it easier, they weren’t derailed by the losses.

My future wife, Annie, and I went to Chicago for the St. James Races back in the mid 2000s. She asked me on the way to the races, “What are we going to do after the races? Should we try to find some friends and find a cool place for dinner?” I stammered and snapped, “How am I going to answer that? I don’t know what kind of day I’m going to have.” She looked at me, puzzled, “What’s that got to do with what we do tonight?”

She had a point.

The game had consumed me – my self worth based on how fast the horses were running. I thought I was a better person when the horses won and a worse person when they lost. It was a constant battle.

Dealing with defeat.

Similar to recovering from bad races, it’s a learned trait that takes a lot of learning. I won 152 jump races in my career, which means I lost 850 races or so. That’s a lot of defeat.

Allen Jerkens used to say the same thing, “I’m in the Hall of Fame, I’ve won nearly four thousand races. I did the math one day, if I won at 20 percent, that means I lost 16,000 races…” Actually, according to Equibase, the Chief lost 17,117 times. And he was never good at dealing with defeat.

Sometimes you have to kick a few buckets.