During the Revolution, George Washington, spotting a group of Connecticut cavalry officers on fine gray horses, inquired with one Captain Lindsey about a set of Arabian horses sired by a stud named Ranger. As it turned out, the sultan of Morocco had gifted Ranger to a British captain who had left the horse on American soil as a breeder. Washington, who had an eye for fine horses, bought the horse, which he subsequently crossed with another famous Arabian offspring, the mare Othello. The mare sired Magnolio, a chestnut stallion, who raced and lost at the Alexandria, Virginia track against a horse belonging to George’s friend and sometimes rival Thomas Jefferson. Cutting his losses, George sold Magnolio to his friend Henry “Light Horse Harry” Lee for several thousand acres of land in Kentucky.

In many ways, gambling on horses in the 18th century was easier than it is today. Most of the “gentlemen” who bet on horses knew each other; they knew their horses, including the bloodlines of the opposing horses. The riders were often servants or slaves, and while the races were an often brutal sport for the riders, for the gentry, they allowed for stylish displays, including exhibitions by ladies sporting new dresses and parasols. Race days, which often coincided with court days, legitimized aristocratic values, including wealth, competition, and independence. The scene also allowed men to let off steam and to settle financial scores in a peaceful, even genteel manner.

Our Founding Fathers—particularly those of a Southern persuasion—gambled not only on horses but pretty much everything else. Virginia, known as the Old Dominion, spawned a gambling tradition grounded in age-old British traditions. Gambling houses in London in the 17 th and 18 th centuries became playgrounds for the rich and famous—maybe not unlike a gilded Trump Casino on a fine day. Virginia’s wealthy but cash-strapped planters—like Jefferson and Washington—moderated their gambling in ways that the British aristocrats often did not need to. Nevertheless, a northern visitor to Williamsburg, the capital of the Old Dominion, commented that Virginians were “much addicted to gambling, drinking, swearing, horse-racing, cock-fighting, and most Kinds of Dissipation.”

Indeed, Washington and Jefferson’s fellow Virginians generally insisted on having as much fun as their English cousins. They bet on everything from jumping frogs, cocks, dogs, rats, and dogs killing rats as well as bears killing men—they even bet on the precise day and hour of an expected child’s birth. Little wonder that in New England, gambling was often frowned on by Puritan patriarchs, who called it a dishonor to the Maker and dealt out firm lashes for lascivious gamesters.

Scholars, who have considered the precarious existence of Colonial Americans, contend, however, that gambling offered some men a framework for skilled decision-making in a rough and tumble life that was a gamble unto itself. In other words, gambling often imitated real life.

For George Washington, who grew up across the river from bustling Fredericksburg, small-time gambling fast became a way of life. He made his first wager at a young age. In 1748, at 16, he noted in his accounts that he won two shillings and three pence from his sister-in-law at whist and five shillings at loo from his brother. Loo, also spelled “lu,” was a card game that had arrived in England about 1660, when the Roundheads ceded power back to the Crown. The writer Alexander Pope used the game as an analogy in his famous mock epic “The Rape of the Lock,” opining, “Even mighty Pam, that Kings and Queens o’erthrew, And mow’d down armies in the fight of Lu.” In that sense, it might be considered somewhat of an aristocratic game.

Not so for another of Washington’s major amusements growing up in cobblestone streets named after English kings, queens, and princesses. Here he also acquired a taste for one very special and ancient blood sport: cockfighting, a pastime he would continue to enjoy throughout his youth. Depicted in the unearthed mosaics of Pompeii, cockfighting was a sport with a long history, and anthropologists have spent many hours and chapters analyzing the significance of the sport, including as it relates—or not—to male virility.

A simple description of an 18th century fight makes clear the wild popularity of cockfighting in Washington’s day. A traveler to a nearby Virginia town described a “cockpit; surrounded by many genteel people; promiscuously mingled with the vulgar and the debased. Exceedingly beautiful cocks were produced, armed with long, sharp, steel-pointed gaffs, which were firmly attached to their natural spurs. The moment the birds were dropped, bets ran high. The little heroes appeared trained to the business, and not the least bit disconcerted by the crowd or shouting…”

The imported English sport was popular in Williamsburg as well, and the president of the College of William & Mary would eventually ban students from taking part in cockfights in 1752, when Washington was only 20.

George’s own love of competitive sports and gambling did not dissipate much through the years, but during the Revolution he grew frustrated with the amount of wanton gambling in the ranks of the Continental Army. He felt it might ruin morale. In 1776, an order issued from his headquarters sternly warned that, “All officers, non-commissioned officers and soldiers are positively forbidden to play cards, or games of chance,” adding, “At this time of public distress, men may find enough to do in the service of their God and country, without abandoning themselves to vice and immorality.” Such orders did little to dissuade soldiers, including those starved into gambling for acorns to eat at Valley Forge.

Throughout his life, Washington carefully considered the right times to hold his cards and when to fold them. He wrote to his nephew, Bushrod, in 1783 that he should “avoid gaming,” but acknowledging that, “To all those who enter the list, it is equally fascinating; the successful gamester pushes his good fortune till it is overtaken by the reverse,” and thereby cuts his losses. And so it was that Benjamin Franklin, with a tip of the hat from an admiring Thomas Jefferson, financed the Continental Army’s vast cannon industry through a lottery and George, as its commander, took immeasurable risks on the battlefield. As he prepared to cross the Delaware, General Washington is believed to have scribbled “Victory or Death!” on a scrap of paper.

While admonishing his stepson and nephews not to dawdle in gambling dens, later in life George happily took on the role of “master of ceremonies” at jockeys’ clubs in Fredericksburg and Alexandria. From his diary entries, it is apparent Washington was an avid horse breeder and an even more passionate racing fan. His affection no doubt stemmed from a childhood in which race days were a veritable carnival of delight in Fredericksburg. Yet, from his account books, it is also apparent that George preferred mostly small bets on horses. He appears to have relished the competition and cordial sportsmanship more than the prospect of financial gain.

Philip G. Smucker, author of Riding With George: Sportsmanship and Chivalry in the Making of America’s First President, to be published by Chicago Review Press on July 1, is a journalist, professor, research fellow at the National Library for the Study of George Washington at Mount Vernon, and the author of My Brother, My Enemy and Al Qaeda’s Great Escape. He lives in Virginia.