The City of London boasts a history dating back more than 2,000 years. Legend has it that Brutus of Troy defeated a pair of giants to establish “New Troy” on the banks of the Thames, and an Iron Age tribe called the Trinovantes  settled the area before 500 BCE.
The first evidence of permanent habitation, however, are the ruins of Londinium , a civilian town created by conquering Romans around 50 AD. No doubt there was gambling even then, as Roman legions were renowned for playing a dice and board game called “Duodecim Scriptorum”  (“twelve writer”), that would later evolve into “Tabula” (“tables”) and eventually Backgammon.
To ancient Romans, gambling was a metaphor for Life. In the 1st century, Pliny the Elder opined, “We are so much at the mercy of chance that Chance is our god.” Such was their proclivity for betting that long after the Roman Empire collapsed, wagering on games of chance and sports were manifest everywhere the Romans had been, and especially in London.
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From Middle Ages to Maturity
Not much is known of London’s gambling activities in the early Middle Ages. The area’s Anglo-Saxon heritage began in the 6th century with traders from Middlesex creating an outpost adjacent to the Roman enclave. Viking attacks dominated the 9th century. When Alfred the Great (849-899) refortified the old Roman walls, the city became known as Lundenburgh, which was later shortened to London.
Under the rule of William the Conqueror (1066-1087), betting on the outcome of jousting events gained a following in London and the surrounding countryside. By the 12th century, the tournaments had become so popular that King Henry II (1154-1189) banned the sport, not to stop the wagering but because so many of his highly trained knights were unnecessarily injured.
During the 13th century, soldiers returning from the Crusades brought new forms of recreational gambling home to London. One of them was a dice game called “Hazard,” perhaps named after the castle town of Hazarth or a derivation of the Arabic words for “the dice”—al zar. Hazard became wildly popular among Londoners and spread far and wide. In the centuries that followed, it would travel to France and then America, where it became the prototype for “craps.”
In the 14th and 15th centuries, London residents developed a penchant for wagering on just about anything, from archery contests to the weather. One common form of late medieval wagering was a coin flipping game called “cross and pile,”  a forerunner of “heads or tails.” Another was a ring-toss game called “quoits.” And it was during this period that card games became popular. Despite bans and attempts to limit it, gambling continued to grow.
By the time Henry VIII (1509-47) came to power, the betting craze was rampant, driven in part by the new London rage, a three-card game called “Bragg,”  a precursor of poker. Board games were consuming people’s time and money, too, including Queek (a checkers-type game) and Fox & Geese (a pursuit game).
To bring the army in line, the king banned his men from gambling, while hypocritically allowing it at court. Nonetheless, London bet-takers continued to offer intriguing wagers. When one of Henry’s wives, Anne Boleyn, was put on trial with her brother for treason and incest, odds of 10-to-1 were offered on an acquittal.
Henry’s successor, Edward VI (1547–1553), restored the legality of “dice and gambling games,” while issuing an injunction against participation by the clergy. But London gaming was shut down once more in 1649 under Oliver Cromwell, who banned the horse racing, cockfights and gambling dens that had become common sights everywhere. Only when Charles II (1660-1685) took the throne did gambling experience its Renaissance in London.
Charles assigned his personal croupier, Sir Thomas Neale, to oversee gambling throughout the city. He was charged with issuing licenses to legal entities and shutting down any noncompliant gambling dens. So well did Neale manage his work that in 1870 London’s King Street was renamed Neal Street in his honor, as was a part of Covent Garden—Neal’s Yard.
During the 18th and 19th centuries, a new betting fad called “pedestrianism”  swept London. Wagers were made on how much time was required to walk, run or hop a given distance. As bets became larger, distances became greater, such as a £20,000 bet on walking to Constantinople in less than a year or traveling to Lapland and returning with a pair of women and two reindeer. In 1872, author Jules Verne based a novel upon this craze, entitled “Around the World in 80 Days.”
Horseracing also captured local interest. The Jockey Club first convened in the Star & Garter Pub at Pall Mall, London in 1750 before moving to its permanent home in Newmarket. In 1875, the city got its own first-class racecourse, Sandown Park, followed three years later by Kempton Park. And bookmakers began popping up soon after, such as Ladbrokes, which began as a commission agent for horses in the 1880s and would grow to encompass more than 2,700 betting shops.
Wagering on team sports gained in popularity, too, as the Football Association was formed in 1863, followed by the Rugby Football Union in 1871, test cricket in 1877 and Rugby League in 1895. And then there were casinos, starting with Crockfords, opened on Curzon Street with the backing of the Duke of Wellington in 1828 and followed by the Victoria Sporting Club on Wellington Street. Today, London has no fewer than 28 casinos, many operated by huge corporations like Coral, Genting UK and Caesars Entertainment.