The Triple Crown Part 1: Best Laid Plans of Mice and Men

Brett Whitehead
May 25, 2013

I started planning for the 2013 Kentucky approximately three minutes after the 2012 Derby concluded. I just finished dinner at Dead Presidents and was sizing up my success post-Derby with Ray and Dead Presidents bartenders Karl and Lou. Over an open-faced turkey sandwich that misleadingly looked like a plate of barf, I savored a $1 exacta ticket that paid out $145. After spending the morning pouring over the horses, I was able to find a long-shot winner and cashed in by pairing him with one of two favorites. Never a stranger to showing me up, Karl also boasted a winning exacta and win ticket, the cumulative earnings of which paid off a full month of rent. As a collective group of horse enthusiasts, we all learned that day that betting the Kentucky Derby was a fantastic risk, because any winning ticket would pay out huge returns due to the large betting pools the Derby attracted. In theory, the inordinate amount of stupid bets meant that a well-thought out responsible bet could win an amount of money usually reserved for stupid betting. Or so we theorized. With that seemingly unimpeachable thought in mind, I bought a round of drinks and planned for next year.


Ray and I became interested in horse racing by accident. We started going to Delaware Park to bet on football games, and found a vice less predictable in nature, but much more predictable in scheduling. The first day we spent betting on horses, I showed up after one hour of sleep at my friend Pete’s beer pong tournament, which was won by no one literally or figuratively. We sat at a bar next to a tall, skinny white guy with a white Eagles baseball cap and a non-ironic mustache and through that guy, we appreciated what the future had to offer. Our friendly neighbor drank Bud Light bottles, staring straight ahead at the races without talking to anyone but the bartender and his sad pile of losing tickets. In solidarity, we yelled at the TV alongside, but not in unison with, our new friend, slowly wasting our money and our afternoon in a haze of light beer and adrenaline.


Nothing makes horse racing in general feel more like a carnival game quite like trying to prepare for the Kentucky Derby. At the heart of the Derby are twenty, three-year-old horses with a year of racing experience. The Derby is a mile and a quarter, which is a length none of the horses will have run at professionally before the Derby. Most races have ten horses, but the Derby has twenty. It is analogous to trying to predict a High School Football National Championship if they added four guys to each side and played an extra 30 minutes.

This is not to say that people donít try. While Iíd like to say that Iím above such snake oil science, a sad collection of horse racing books on my book case evidences my interest in trying to predict the outcome of horse races and my belief that such a science actually exists.

Due to a professional decision in which I decided to spend less of my work day with antagonistic maniacs, I found myself with a lot of free afternoon time the week preceding the Derby. I found the past performances (or PPs) online the Wednesday before the race, and did my best to get acclimated to the field. Two horses caught my immediate attention: FEAR THE KITTEN and CHARMING KITTEN. It was your classic cuteness exacta.

A quick tangent: The horse with the best name never wins. For my bachelor party, I went to the Preakness, which is the second race in the Triple Crown and something I will come back to later. The Preakness was about a month after Mach Man Randy Savage died, and the horse in the five slot was named MACHO MAN. While talking with strangers at the Preakness, a drunk guy in cut-off sleeves and a headband told me that the jockey was wearing a shirt with the letters “RS” on the back, making the Randy Savage connection serendipitous. MACHO MAN went off at 6-1 as the third best favorite, and ended up getting drilled by a horse named SHACKLEFORD. A chant of “SHACKLEFORD, SHACKLEFORD” broke out amongst bettors cashing in winning tickets after the race. Start chanting that yourself right now and tell me how inspired you feel to do anything.

Anyway, as I collected information from various sources, it became abundantly clear that no one who writes about horse racing for national websites has any idea what they are talking about, and if they do, they sure as shit donít want to share it with anyone. Horse racing, much like boxing, has not evolved out of its grifty underpinnings. Much like our friend at Delaware Park, all the analysts are old white guys motivated by money. The advice and predictions available are thinly veiled, so that the horse they like doesn’t become the favorite and ruin their chance of winning more money. Those that don’t give their suggestions outright instead puff up a system of betting, in the hope that you will buy their prediction through another medium. I listened to a podcast where one guy based his system on which horse was most likely to win “personality-wise” and which horse was the “leader of the pack.” All you had to do was go to his website, buy his program for $10.99, and you too could waste the same amount of money betting on names your wife thought were cute.


Karl and I spent the Thursday before the Derby watching and playing with his three month old daughter. Karl is good at many things, but Karl is exceptional at sports gambling. This type of gambling includes, but is not limited to, NFL bets, horse bets, NCAA brackets, Super Bowl block pools, and fantasy leagues. Karl has won the Brutal Horse fantasy baseball and basketball league both two years in a row, including dismantling my heavy favorite, juggernaut basketball team in the conference semi-finals earlier this Spring.

As you would imagine from a new father, Karl was occupied with more pressing responsibilities than trying to predict horse races, but I couldn’t help but to seek him out for advice. Karl believed that last year’s Derby set off a “Year of Good Luck” for him that would end at this yearís Derby. It was my hope that he would have one last magic trick that I could ape off of him for my own personal gain. I hoped the same thing would go for Lou, the person I shared the Derby experience with a year earlier. Much like Karl, Lou didnít get the chance to dive too in-depth into the race, but he did feel a pull toward MALICE PALICE, a horse named after the infamous NBA game where members of the Indiana Pacers went into the stands and fought fans in the Palace of Auburn Hills. Neither Lou, nor Karl had quite the well-reasoned predictions I hoped for, but to their credit, neither of them have non-ironic mustaches either.


Ray doesnít work on Fridays, so on weekends we go to the horse track, he is tasked with buying the past performances. The past performances list all the eligible horses, and tell you the results of each horseís last 10 or so races. Ordinarily, the past performances look like hieroglyphics, so Ray buys the Platinum version for an extra dollar. The Platinum PPs come with a more analysis and pace figures that let you know how fast your horse runs at the beginning, middle, and end of the race. Ray uses this information to make this graph.

2013 Kentucky Derby stats
Figure 1: 2013 Kentucky Derby stats in nice graphical form.

I am not a math person, so this graph generally makes no sense to me. I do, however, recognize that green blocks are better than red blocks. Jess took to this graph like a fish to water, so I hope that this assists you, the reader, in understanding my own analysis of how I ended up with a pile of small white tickets at time of posting.

Winning horses generally come in two categories: Speed horses that jump out in front and win “wire to wire” and closing horses that drift in the background and then kick in a burst of speed at the end while all the other horses are tiring out. Generally speaking, races that are longer are favorable to closing horses and the Kentucky Derby is probably the longest thoroughbred race run all year. Looking at the Derby line-up, there werenít any stand-out horses with closing speed. REVOLUTIONARY was a favorite of the experts, but his opening numbers compensate for the opening speed shown by others in the field. The same thing was true with VYJACK, a horse with good pace figures toward the end of the race, but he was also the late addition who bumped FEAR THE KITTEN from the Derby and therefore ruined my cuteness exacta.

With no dominant closer in the pack, I considered whether or not a horse could win wire-to wire. Two horses in particular, GOLDENCENTS and OVERANALYZE both had well-above average closing pace figures, along with good pace throughout the rest of the race. My thought was that if both of the horses could stay ahead of the field through the final stretch, they could have enough to stave off late charging horses who saved their energy for the end. GOLDENCENTS was over-hyped, but it wasnít reflected in the line. He was owned by Rick Petitno, the famous college basketball coach/adulterer, and was being run by the only African American jockey in the race. Even with a typical Sportcenter level of unnecessary attention, GOLDENCENTS was still behind the 6-1 morning line favorite ORB. I didnít see anything worth betting on in ORB, and built my picks around GOLDENCENTS and all his lucrative green boxes.


For all intents and purposes, the day of the Derby went better than I envisioned. Jess, Ray and I piled into Jessí car and we spent the afternoon in beautiful spring weather watching the Derby on the big screen outside of Delaware Park. We found front-row seats that covered the sun, while a 60 degree breeze made for an ideal, crisp afternoon. The Derby itself could not have been more different, as a rain storm swept into Kentucky and ruined the pomp and circumstance usually associated with the Derby. It is always uncomfortable being wet, but the feeling of being wet in clothes that were already uncomfortable wore on the faces of everyone on the screen.

I wonít get into the logistics of how the afternoon went, because itís boring and I donít really remember. What I will say is that we had generally good success leading into the Derby. Ray and I like to play “pick three” bets, which involve picking the winner of three races in a row. This bet is distinguishable from a trifecta, which is first, second, and third in the same race. This is a good practical bet because if you win the first and/or second leg, you donít have to bet on the upcoming race, and can just carry over the previous bet. At Delaware Park, we usually win about $100-$125 per winning bet (except when you end up with three favorites winning and get $8.50 for the hardest work you’ll do outside of actual work -ed.), and Iíve won about eight of them in my lifetime.

Going into the Derby, we had one the first leg on two different pick three bets, but didnít close out the second or third. Our luck got better going into the Derby, where we correctly picked the winners of the ninth race and the tenth race. This meant that if we picked the winner of the Kentucky Derby, we would cash in a monster pick three bet, and also be alleviated of our rental obligations for the month of May. Along with the pick three, I placed five horses in an exacta bet, meaning that if two of those five horses came in first or second, the bet would win. A $1 bet for each permutation cost me $20 in total. In honor of Lou, who couldnít make it because of work, I tossed $4 on MALICE PALICE to win. Noted ESPN buffoon Hammeriní Hank Goldberg deemed MALICE PALICE his dark horse to win because of the weather conditions, so this bet was based on more than Louís earlier text message. I had approximately $6 left, so I placed a random collection of trifectas at $1 each. These were mostly random collections of horses I had bet on in the exacta and sporadic favorites placed in to hedge my bets. Armed with a fist-full of racing tickets, I left Delaware Park thinking confident that Ray and I would be throwing around money later that evening.


The tough part of writing an article where everyone knows the ending is trying to convey the suspense before the race started. First, Dead Presidents is usually good luck. Both Ray and I celebrated there after our weddings and Iíve seen more than my fair share of Philadelphia playoff games wolfing down hotdog specials. I also like to go there after big days at Delaware Park to buy everyone fancy drinks off the “fancy drink menu.” It builds camaraderie.

Brett's folly
Figure 2: Brett’s 2013 Kentucky Derby bets.

I laid my tickets out on the bar as shown in Figure 2. If you look close enough, you can see the steak special, which I planned on ordering if I won. If I didnít win, I told everyone that I would just get a salad. Steaks are for winners, and to be honest, it really felt like I had enough irons in the fire to pull this one out. I canít stress enough how gross the track looked due to the rain, and in such circumstances, I felt like there was a good chance that the front running horses would get a lead, and then the closing horses wouldnít be able to find the extra gear with all the mud. Horse racing commentators like to bring up statistics, like they mean anything in the context of wild animals running in a circle, so I was consistently reminded that no horse had run wire-to-wire since 1972. In spite of the history, this felt like a fairly reasonable prediction. As the horses began their promenade, which when all the horses walk around in a circle so you can see which horse looks the best, I got about five different texts from friends sharing their guesses. Only one person, my friend Dan, believed that the front-runner ORB was going to win. Dan grew up with horses, and he therefore started a frenzy of wild betting one afternoon by predicting horses based on how good he thought they looked, ignoring their race history completely. This technique included, but in fairness was not limited to, looking for horses that had foam between their butt cheeks. No joke. Apparently, foamy cheeks indicates that the horse is sweaty and ready to run. While I admit I checked all the horsesí butt cheeks before the race, Danís prediction seemed improbable. He didnít read the past performance and he surely didnít put in the work that I did. I dismissed all texts and watched as the race began, waiting for one out of approximately 20 bets I had to come through.


That is until the race finished and ORB destroyed all competitors and all of my bets by storming down the backstretch. When the first four horses passed the finish line, I didnít even check my tickets to see if I hit the winner by accident. ORB was the clear winner, and the two horses following him were nowhere on my radar. To make matters worse, GOLDENCENTS, the genius pick of the Brutal Horse brain trust faded halfway through the race and ended up in the bottom third. Among the five horses I predicted for the top two spots, only REVOLUTIONARY placed in exotic bets, coming in fourth. The race was instantly deflating. What was once a collection of potential free rent payments, fantastic anecdotes, and fancy dinners became just a pile of trash I needed to get rid of.

I still got the steak, although it wasnít quite as delicious due to the aftertaste of defeat. Winning at horse racing was still about money, but I wanted to defeat the system first and foremost. Itís one thing to lose a hand in blackjack, and itís another thing entirely to waste a whole week looking over past performances, listening to podcasts, talking to friends, and developing a narrative, only to lose when the stupid favorite does exactly what everyone thought he would do.

After dinner, we still enjoyed the evening the way winners enjoy the greater Wilmington area. We bought cigars at the shady cigar store in Trolley Square and played Settlers of Catan in Rayís beautiful backyard. As for horse racing, I wish I could say that I learned a lesson from this race, but I clearly havenít. Iíve never been someone who swore off drinking when they were hung over, and I surely wasnít going to swear off horse racing after one wasted afternoon (you mean one wasted week -ed.). In two weeks, Delaware Park started live racing on the same day the second leg of the Triple Crown was run in Maryland. Given my history with both races, I assumed that weekend would be my revenge. Both against horse racing in general and ORB specifically.
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