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.