The Beauty of Luck



I am looking forward to Saturday’s Whitney at Saratoga. With our 4th child’s due date on August 4th, this might be my last day to play the races without clutching a newborn while whipping the couch with a diaper, rooting my horse home.

I’ve never had much success at Saratoga—I came up on the small fields and obvious favorites of Hawthorne and Arlington. Every horse at Saratoga looks like a winner to me, and every connection could throw some weight around the Chicago circuit.

Over the years, I’ve gotten better at handicapping these fields but my biggest score at Saratoga came on Whitney Day in 2014—and I didn’t have to handicap at all.

Whether in name, in aspirations, or in mind—horses have a deep connection to dreams.  Horse Racing Nation has 2,594 horses listed with the name Dream in it. In the 19thcentury it was not uncommon for people to wake up with a vivid dream and take it to Old Aunt Dinah, or whomever was pedaling hoodoo with their voodoo, for interpretation on how it related to the numbers racket or the horses racing that day. (See: Old Aunt Dinah’s Policy Dream Book: Comprising a Brief Collection of Dreams, Which Have Been Interpreted and Played with Wonderful Success to the Dreamer.) Nothing is as pathetic yet endearing than a person who believes deeply in their luck—that personalized logic of chance operating just beneath the rhythms of life.

I didn’t ask to dream about horses, the horses just came to me in my dreams. It started with San Giacomo. I dreamt him crossing the line first, and I tried to bet everything I had his next two starts, but the races were canceled with the December arctic blasts sweeping Chicago, and I said, “Well, that’s my luck.” San Giacomo won his next nine races, the first of which came on my birthday.

Fast forward five years and at least a dozen dreams more. In the midst of a vivid summer trying to earn a part-time-living betting horses, I had my Whitney dream. So many monster horses running that year. The three-year-olds included Bayern, about to become unstoppable with the blinkers who would go on to win the Breeders’ Cup Classic; Shared Belief, emerging undefeated and possibly as the next Zenyatta; California Chrome, leading us to believe that a Triple Crown was still possible. In the Whitney that August a memorable field of older horses loaded into the gates: Will Take Charge, 2nd in the Breeder Cup Classic and a Travers Winner; 3-5 favorite Palace Malice on a four-race win-streak; Itsmyluckyday also in form who won the Woodard next out which would have made it 5 in a row; Romansh; Last Gunfighter; Golden Ticket; Prayer for Relief; Departing; and then there was the speedster Moreno, who set fast fractions but most often came up short.

You could build a case for most of these horses, but I didn’t need to handicap to know Moreno was my pick because a month before I had woken up with a song in my head that at this point in my horse racing dreams, I did not need Aunt Dinah to interpret:

“Waking up in a basement in Moreno

wondering if there’s someplace I ought to go

brushed my teeth and played boogie woogie on piano

realized today that I just might be free.”

I have always heard Dr. John singing it. Or Randy Newman. But more pressing than songwriting at the time was my need to make money. I had lost my position at a local college in Chicago. I had two children, a patient, lovely wife, and I was working up the bravery to go all-in on the horses and my writing career. There I was lying in my bed with this song, wondering how crazy I had grown, dreaming of horses, dreaming of songs—could they really cross the wire together?

I got on my bike and I rode the lakeshore path heading to the café to write, but I stopped on a bench next to the retired immigrants of Edgewater, and I stared at the summer waters of Lake Michigan, those perfect mornings of warm sun and cool breeze. And I wrote the rest of the song, including the chorus:

“There must be

someplace for me

somewhere beautiful by the sea

I must confess

I have faith in duress

I believe my search is for the best.”

A month later and a furlong from that same bench, I pulled over on my bike and watched the Whitney on my phone. $250 riding on a 10 – 1 horse whose name was in a song that came to me in a dream. I had been writing at Dallop, a neighborhood café in Uptown, right off the Lake Shore Path. It felt like my life revolved around the Lake Shore Path those early years of being a father. Pulling my kids in the Burley to the zoo. Escaping my worries. Contemplating where we should move, how I should earn money. Becoming a runner, quitting smoking. Feeling for two months of the year like I had found paradise.

My in-laws were over at our apartment that afternoon and our relationship sucked—at that time my father-in-law was telling my wife that I was ruining her life. So I had gotten away to write, and when it was time to head back for the tail-end of their visit, I took two more minutes straddling my bike and watching a dream come true. Wire-to-wire. 10 to 1. Junior Alvarado on board, Eric Guillot’s most prestigious win. The cherry on top of my horse racing summer when I had $23,000 in winning tickets, though I put $20,000 through the window.

My Whitney dream is more than the money made that day—it is a highlight moment of my life that has left me bewildered by the intriguing beauty of luck. What besides luck could design a more beautiful package than a winning horse wrapped up in a song?


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  • Love this piece. Can relate to pausing your day to day activities to watch a big race in an odd place. Kevin’s journey could be an entire novel. Hope to read more.

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