Fortune brings in some boats that are not steered.—William Shakespeare, 1610
Every spring the attention of horse-racing fans and bettors focuses on Oaklawn, the hundred-year-old racetrack in Hot Springs, Arkansas. Oaklawn hosts one of the more propitious of Kentucky Derby prep races, the Arkansas Derby, which has played an outsize role as a showcase for three-year-old colts rolling into form just in time for the big stage a few weeks later in Louisville.
This year I went online to watch the races at Hot Springs less for the Arkansas Derby than for a race earlier that same afternoon, the Oaklawn Handicap. I liked a horse called Upstart and had been waiting for months for precisely this set of circumstances to bet on him. Upstart had been one of the outstanding colts on the East Coast last year before tailing off at the end of the spring. Rested in the late fall and early winter, he’d made a successful return to competition in March in the Razorback, a stakes race that promised to tighten him up for the Oaklawn Handicap. Still, the public perception remained that he was a money burner, a horse who had never lived up to his billing. His odds would be longer than they should, particularly since his rival this afternoon, Effinex, was seen as a potential superhorse. He also had an underrated jockey in the saddle. After I pored over the Daily Racing Form and its welter of data, I saw more and more indications that Upstart would rise to the occasion. With his odds floating just under 6–1, this was the time to pull the trigger. I transmitted $200 through my online wagering account.
Upstart didn’t get the message. He broke just a step slow out of the gate while Effinex was all business, stalking the pacesetter before making a decisive move as the horses turned for the homestretch and kicking clear as an easy winner. Upstart finished fifth, the victim of a bad trip at best (or overstated talent, more likely).
Odysseus, Saved from Shipwreck by Minerva, Landing on the Island of Calypso, by Pierre-Charles Trémolières, 1737. © HIP / Art Resource, NY.
I lost my $200 but not my perhaps delusional sense of confidence that I’ll win on a horse like Upstart more times than not. That is the name of the game for anyone who bets on horses as more than a recreational whim. It’s one of the paradoxes of betting on racing that even when you lose, you still feel as if you control your destiny in a manner that makes handicapping somehow different from other forms of gambling. It’s a long-haul effort of winning and losing, and in the process making ever more refined judgments, including when to actually plunk down a bet and when to pass. All types of gambling, from buying a lottery ticket to sitting down at a hand of poker, involve playing with chance, with wagering on forces (the hand that gets dealt, the toss of the dice) beyond your control. But handicapping horses has a more complicated relationship to luck and to the devil-may-care abandon to chance purported to constitute the gambling experience, which is why those bettors who do the best at predicting the outcome have to all but banish the word luck from their vocabulary. If all gambling is about playing with the irrational, the handicapper has an almost undying faith in the rational.
It’s no surprise then that luck doesn’t appear in the short glossary of racetrack slang that H.L. Mencken included in the second supplement to The American Language and is virtually absent from The Argot of the Racetrack, the scholarly lexicon published in 1951 by the linguist David Maurer. There you’ll find page after page of terms that have found a home in mainstream English (blinkers, nightcap, dope) along with faded novelties (oil in the can for a sure winner, on the Bill Daley for a horse that leads a race from start to finish, meat ball for a concoction to drug an animal) and the jargon of tip sheets and touts and betting by systems. But the absence of words for chance is no accident.
Much of the reason that handicapping seems almost blinkered with regard to luck has to do with the history of betting in the twentieth century. In the early part of the past century, pari-mutuel wagering systems began to make trackside (and off-track) bookies obsolete. These systems totaled the amount bet in a race, subtracted the 15 percent or so that went to the state as a gambling tax and the racetrack’s cut of the action, and generated the odds on a horse based on how much had been wagered on each entry. Thus, the horse that had the most money bet on it had the shortest odds. From its implementation in Kentucky in 1908 to its almost universal incorporation at nearly every track in America by the 1930s, pari-mutuel wagering rationalized how gambling on horses took place—and it shifted the objective of handicapping from outsmarting the bookie to outsmarting the public, since it was the public that established the odds in any race.
Keeping the idea of luck at bay isn’t the easiest thing to do when it comes to horse racing. Horses have been synonymous with luck, both good and bad, for eons before anyone bet on them. From folk traditions to the backstretch at Belmont, these animals are head-to-toe billboards for superstition, from their luck-generating horseshoes to the auspicious (or inauspicious) markings on their foreheads. At the track, even their names sometimes conjure good fortune. This isn’t anything new. The classicist J.M.C. Toynbee once tallied the names of some 480 racehorses mentioned in ancient Roman sources and found at least a quartet that eponymously denoted their own good luck: Felix, Felicissimus, Faustus, and Secundus—incidentally, about the same proportion of names that, in an echo of Effinex, were terms of abuse, like Parasitus (toady), Lues (pest), Latro (thief), and Leno (pander). “Lucky” horses have won a share of Kentucky Derbies (the gray Silver Charm in 1997 and the suavely named Lucky Debonair, with Willie Shoemaker in the saddle, in 1965), although it wasn’t until the forty-fourth edition of the race that a Lucky first appeared (Lucky B, who finished a dawdling fifth in 1918). In recent years, the moniker has seemed to attract nothing so much as its unlucky opposite. Lookin at Lucky, the slight favorite in the 2010 Derby, finished out of the money. Even unluckier was the 2015 prospect One Lucky Dane, who fractured a bone during a workout for last year’s Derby and hasn’t raced since.
With all this luck running around, it may sound like an exercise in bad faith to expel it from your way of thinking—all the more so in a sport where money is won or lost depending on how a skittery, spindly-legged, mishap-prone animal with a feathery human on its back will run in a pack around a tight oval. Yet it is built into handicapping theory and practice. It gives rise to the great philosophical split among horseplayers: whether the goal of handicapping is to find the most likely winner in a race or to search for betting opportunities based on value—to look for long shots who promise to run better than their odds and to play against heavy but unworthy favorites. “When you spread out a Daily Racing Form with fifty races in it,” the turf writer and handicapping guru Andrew Beyer told the New York Times, “and you can bet them all, and you know there are a lot of puzzles in there that are solvable—well, it’s totally engaging.” But without the knack for knowing when not to gamble, playing fifty races is also a way to bottom out fast. That acumen places handicapping somewhere between poker and picking stocks in the aleatory imagination.
The word handicapping took its current meaning during the post–Civil War horse-racing boom, when a new generation of industrial magnates poured money into the construction of opulent racetracks in New York, Chicago, St. Louis, Baltimore, and San Francisco, and racing outgrew its largely Southern country-fair roots and became a modern urban spectacle. Only baseball rivaled it as a big-city sport for the masses. In the first years of Reconstruction, the New York area could boast of fashionable racetracks in the Bronx, at Coney Island, and at Prospect Park, as well as in Long Island, in Paterson and Hoboken, and at the Jersey Shore. (Saratoga Springs, with its first summer meeting in 1863, was already established.) But the roots of the word handicap are older, originally linked to a bartering game called hand-in-cap. The word comes up in Samuel Pepys’ diary of September 1660 (“some of us fell to handycapp, a sport that I never knew before, which was very good”) and mention of the game extends back to the fourteenth-century narrative Piers Plowman.
Hand-in-cap involved players staking various items—say, a pocket watch and a cow—and forfeiting money on the outcome of the game. A third party, acting like an auctioneer, announced what he imagined the values of each item to be and how much one party would owe the other if they were traded. Both players then put coins in caps, put their hands in the caps, and pulled out a coin to signal whether they agreed with the umpire’s judgment. If they both pulled out coins, the trade went through and the umpire kept the forfeiting money; if neither did, the trade was voided but the umpire still kept the ante. But if only one player held a coin, the trade was canceled and the player who did pull a coin won the kitty. The game combined the possibility of a small reward for taking a larger risk by agreeing to trade an expensive item, but it also drew on the umpire’s talent for correctly assessing the difference in value between two things.
The idea of a handicap—a way of equalizing the chances of horses with different abilities—came to have sweeping applications in racing and transformed the sport. After all, a horse owner might otherwise have little incentive to send a lesser animal up against a world-beater, and the solution arrived by asking the faster horse to carry some amount of extra weight—the handicap. The Oxford English Dictionary gives examples from as early as 1787 of races described as handicaps, where horses were assigned weights based on their ability. By the first part of the 1800s, the word handicapper had already come to designate the racing official or organizer responsible for determining those weights based on a horse’s chances of winning, which both attracted owners to enter their pokier steeds and enticed gamblers to wager on them, legally or otherwise. A vast chunk of the major races in England, the United States, and Australia incorporated the principle of the handicap in the nineteenth century as an ingenious way to level the playing field. Incidentally, handicapped in the sense of physically or mentally challenged didn’t emerge until significantly later, in the late 1800s. By that time the word had also further migrated to the other side of the racetrack to describe what bookmakers and bettors did when they sized up the horses in a race and assigned their own set of odds on their likelihood of winning.
The leveling principle of the handicap worked well when translated to other sports like golf and tennis but perhaps nowhere as spectacularly as horse racing. More than two centuries after it was introduced, handicaps are still an important ingredient of racing, with weight allowances based on a number of factors, including the horse’s age, total winnings, and types of races won, applied to the field.
When American racing burst onto the scene, handicappers represented a new breed of gambler, a perfect parallel to the Gilded Age captains of industry who built the postwar palaces of racing, as Jackson Lears noted in his celebrated history of luck in America, Something for Nothing. Legendary plungers had always been drawn to horseflesh, but the handicapper signified something different from the likes of such easy come, easy go speculators as John Warne Gates, whose large wager on an English race gained him the nickname “Bet a Million” Gates. The handicapper was by contrast a stealthy and enterprising contrarian bestowed with hard-won knowledge, patience, and an eye for opportunity. In a sport and culture rife with con artists and touts, he made his money fair and square, which is what linked him in the imagination with the self-possessed business tycoon. Both shared the gospel that hard work, not luck, was what separated winners and losers.
One of the most enduring how-to-win-at-the-track testimonials—a kind of founding document in a robust publishing subgenre that mixes self-help and racing wisdom—is nothing short of a paean to the joys of perseverance and calculation. Racing Maxims & Methods of Pittsburg Phil (1908) offers the posthumous pointers of George E. Smith, a turn-of-the-century horseplayer known as Pittsburg Phil, who parlayed an eagle eye and an actuary’s taste for precision into a $2 million estate before his death in 1905 at just over forty. In the book Phil relates the mind-set it took to beat the game.
Now what do…successful handicappers know about horses? Well, I might say, incidentally, that they know the capabilities of every good horse in training, and have an accurate idea of what he will do under all circumstances. They know his habits, and his disposition as well, and perhaps better than you know your own brother. They know when he is at his best and when otherwise. They know what weather suits him, what track he likes best, what distance he likes to go, what weight he likes to carry, and what kind of a jockey he likes to have on his back. They know what the jockeys can do and what they cannot do, and in addition to that, they are close observers in the betting ring. If there is anything wrong, it generally shows in the market. Does not that mean some study? Can a man who regards racing as easy, who spends only an hour or so looking up the “dope,” figuring upon horses as they would on a piece of machinery by time and weight, know as much as they do? It takes them years of constant close, coolheaded observation to acquire this knowledge, and at that the returns are often meager.
Pittsburg Phil was only the best known of a number of handicappers whose success made them minor celebrities, their every coup covered in the nascent sports sections of newspapers around the country. In his , Phil gives advice from the grave about handicapping concerns ranging from the role of jockeys to the proper way to train a Thoroughbred to the paramount tip of keeping detailed records on a horse’s entire career. But like most of the horse-racing literature to follow, his book is largely mum when it comes to luck. However much racing has changed since Phil’s time, once you begin to believe in luck rather than the odd combination of skills, apprenticeship, and gumption that can lead you to think you can beat the races, you’ve abandoned the handicapper’s creed.
But what a strange skill to have, and how long the apprenticeship! I have been at it as a handicapper with varying levels of seriousness and success for most of my adult life. It was more than twenty-five years ago that I first started going to the track and began to think that there was some rational way to order the raft of digitized information that every horseplayer grapples with in any track program or the pages of the Daily Racing Form, and I still happily devote an inordinately large amount of my time to following and betting the horses. There’s nothing particularly original about my autobiography: I’ve had some terrific scores, and I’ve had long fallow periods where nothing worked. I’m not a really large bettor, and I’ve had both exceptionally good days and alarmingly awful ones. I’ve hit bets that paid in the very low five figures; I also once blew through a $5,000 bankroll in a couple of weekends betting at small racetracks in Iowa and Oklahoma, figuring wrongly that I was a sharper player than the rubes and rustics who followed those races. But one of the remarkable things about gambling on horses is that losing leads more to humility than to disillusionment.
The Farmer’s Wife and the Raven, by George Stubbs, 1783. © Philip Mould Ltd, London / Bridgeman Images.
I was introduced to handicapping through the Racing Times, the short-lived competitor to the Daily Racing Form started by the British tycoon Robert Maxwell. The Racing Times’ run was about as brief as my Iowa bankroll, but it was an eye-opener for a fledgling handicapper. It was edited by the former New York Times turf writer Steven Crist, who cut his teeth on dog racing at the Wonderland course near Boston. Where the Form had gotten dreary and stained your hands with its cheap ink, the Racing Times was a spanking new tabloid, elegantly laid out on oversize, almost glossy sheets. Most important, it published Andrew Beyer’s gift to handicapping, a rating system called the Beyer Speed Figures, which helped solve a conundrum that had long plagued handicappers: how to convert a horse’s performance on a given day into an objective and reliable number.
For horseplayers, Beyer’s ratings were nothing short of a Copernican revolution. Because horses race at a range of distances and the surfaces (and inherent speed) of racetracks vary greatly—what counts as a good winning time over the sunbaked dirt in Southern California will be much faster than a race at the same distance in New York—it was difficult to quantify a horse’s level of talent. Beyer’s figures provided an accurate sense of how fast a horse had run on a given day—a real boon when horses were shipped from one racetrack to another or went from competing in cheaper races to classier affairs. When Crist made the jump from editor of the Racing Times to publisher of the Daily Racing Form six years after the former closed shop, the Beyer numbers had already made the migration, bringing the revolution to the masses.
Most handicapping today in one way or another revolves around speed figures. They so thoroughly changed how most people go about the business of handicapping that it’s hard to recall the old methods that reigned before Beyer—so much so that they became much less profitable as a handicapping tool as their popularity increased. Novelty runs out fast in horse racing. There’s not much of an edge provided if the information is available to anybody who buys a copy of the Form. Beyer’s numbers quickly became an industry standard. Yet there were even more sophisticated and more precise speed figures out there, and the theory of how they worked was as convincing in action as it was exotic in appearance.
The figures that the Ragozin Sheets published were older in provenance than Beyer’s numbers, originating in the 1950s with a businessman named Harry Ragozin and perfected by his son Len, whose fledgling career as a journalist at Newsweek had been derailed in the McCarthy era by his lefty politics. Their innovation was not just a better way to quantify speed—the Rag number incorporated everything under the sun that could affect a horse’s performance, from whether a horse raced close to the rail to the weight the horse carried to the effect of wind speed—but a better way of presenting the information. When you read the Racing Form, you see row after row of sentence-like strings of numbers, each representing a race that the horse has run. The Sheets, by contrast, turn the visualization of information on its head. They plot a horse’s lifetime of performances on a graph, which makes it possible not just to compare horses against one another but in essence to compare a horse against its own past performances.
Each Sheet—a single piece of unbound paper for each horse in a race—narrates a kind of encapsulated and encrypted equine biography, most of them filled with performance peaks and valleys as dramatic as the booms and busts of Gilded Age stocks. At a glance you can picture how a horse’s ability unfolds over time, watch its improvement, see its decline. Performance cycles, as horses approach their best races, didn’t show up in the Form but were often obvious on the Sheets, none so famously as the phenomenon of the bounce—the supposition that a horse that runs an inexplicable and eye-popping effort can be expected to regress, often severely, in its next race. Len Ragozin liked to credit his appreciation for dialectical materialism in describing the bounce, raising contrarianism to new handicapping heights.
Luck is believing you’re lucky.—William Carlos Williams, 1947
The Sheets were esoteric and required a whole new approach to handicapping, a basic unlearning of what I’d spent a decade trying to crack. But what conversion, religious or otherwise, doesn’t require that devotees see the world in a new light? It wasn’t enough to use the Sheets—you had to learn to read them, to spot the hints of equine improvement or the sometimes nebulous long-term cycles where a horse might be returning to its best form. They weren’t easy to purchase (in New York, before the download era, if you weren’t at the racetrack, they were available only at the company’s dingy office on a side street near the Strand bookstore or at a forlorn newspaper stand in Midtown) and, at $35 per racetrack a day, they weren’t cheap. But their inaccessibility and costliness had their own kind of mesmerizing appeal.
To Sheets percipients, there simply isn’t a more precise approach to handicapping. More than that: the Sheets are the closest you can get to the objective translation of how a horse performs converted into pure points of data. To others, they look like tea leaves. Even those who subscribe to a rival set of speed figures from Thoro-graph—a company started by a onetime Ragozin employee—call orthodox Sheets players Kool-Aid drinkers for the rigidity of their faith.
For a long time I used to invite people who didn’t know anything about racing to go to the track, and I’d attempt to explain to them why I thought the Sheets worked and how I used them—which by now is for the most part synonymous with how I handicap, so it might be better to say that I tried to teach them how to handicap. It usually sounded so sophistic that I’d revert to teaching them how to read the Form, which at least carried a romantic whiff of the old days of horse racing, when you’d actually see people flipping through its pages on the subway or buying it at a newsstand. (Just try finding a copy now.) I realized pretty quickly that to a novice, my words sound like nothing so much as a kind of investment in magical thinking.
Anarchy (Hour of the Wolf), by Andres Serrano, 2011. Cibachrome print, silicone, acrylic, 50 x 60 inches. © Andres Serrano, courtesy the artist and Edward Tyler Nahem Fine Art, New York City.
A defense of handicapping would likely hinge on how much it’s unlike pure games of chance. But the real-time demonstration often doesn’t look like anything more than a spin of the roulette wheel, and all the handicapping talk can sound like the stuff of sortilege. I used to try to disabuse others of the idea. Now I am more likely to fall back on the old language of luck and let friends enjoy the track for what it is—a not unhappy mix of betting and the sight of breathtaking horses. I always wish my companions luck when they go off to the betting window, hoping they hit a long shot I’d never consider, which everybody knows happens all the time.