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The Toughest Gambling City Of Them All

Chicago history - like its name, which means "river of the onion" - reeks. Political corruption, gambling, and crime were always an unholy trinity in the Windy City, as politicians countenanced gambling that led to crime.

With the westward drive Chicago became a Mecca for small businessmen, land speculators, prostitutes, gamblers, and the camp followers of expansion. Adventurers came in ,from the crowded lake boats where they had passed their time card playing. As a professional gambler described the scene in 1836: "Everybody on board the boat seemed to have taken as much pains to have a pack of cards as to have a second shirt. The passengers were all loaded to the bulwarks with the coin of the realm, many of them being rich speculators and adventurers. Quiet little games were going on fore and aft, everybody from the captain to the roustabouts taking a hand."

Between 1825 and 1837 Chicago popped from a village of 75 to a town of 4100 who were already speculating frenziedly in land when the Illinois Legislature -ranted a city charter. The panic and crash of 1837 put a stop to land speculation but not to the wild growth of the city. Immig:-ants poured in by steamer, wagon, on saddle, and on foot. The Erie Canal was its link to the world till the railroad reached it in 1852. By 1854 Chicago had 60,000 citizens.

By then, like most American cities, it was given to saloons, Sabbath breaking, and crooked gambling dens, and one of the first misdemeanors to meet with legal punishment was the use of "seconds," cards in a pack with edges trimmed and notched so infinitesimally that only a slick dealer could find and produce them at will.

The official history of gambling in Chicago really begins on August 10, 1833, five days after Chicago was incorporated as a town with a board of trustees given authority to abolish gambling. They promptly closed two dens and sent the proprietors to enjoy a short stay in the local lockup. Within a few months and for a quarter of a century thereafter gambling was wide open, and no efforts of reformers to stamp it out had any lasting effect.

"Skin" gamblers were drawn to Chicago like flies to molasses from the first, dealing the usual banking card games plus chucka-luck and roulette in rooms rented for a fee with the gamblers supplying their own paraphernalia. Here verdant players took chances against slick card artists, dice hustlers, and wheel operators, the most noted of whom were H. Smith, Bill McGraw, Dan Oaks, "Dutch" House, and "Little Dan" Brown. McGraw, House, and Brown were the pioneers at bookmaking in the town. When their careers ended in drink and the poorhouse, other rogues replaced them. By 1842 when Chicago numbered 18,000 John Quinn listed George C. Rhodes, the Smith Brothers George, Charles, and Montague Walt Winchester, Blangy Curtis, John Sears, Cole Martin, and "King Cole" Conant as the most prominent professionals running their own dens. Customers favored poker, brag, seven-up, cribbage, and even whist, chess, checkers, and backgammon with the house cutting itself in for 10 per cent of the stakes. In addition the men who operated these early gambling houses frequently sat in on games.

Nature endowed John Sears, the only thoroughly honest bigtime professional gambler of his day in Chicago, with the best possible traits and one weakness, gambling. Sears, part French, was tall, dark, and distinguished, beautifully dressed and unfailingly courteous. He had never been known to raise his voice in anger and he was the soul of generosity. When he was not gambling, this educated fellow was likely to have his nose in a book of poetry. While his fellow gamblers found pleasure in whisky and women, Sears's greatest loves after gambling were Robert Burns and Shakespeare. Between his weakness for gambling and his simon-pure honesty, Sears died poor and profoundly mourned.

Cole Martin and "King Cole" Conant pulled out of Chicago for St. Paul, where faro was admired, suckers plentiful, and competition nonexistent. They dissipated their profits in loose living and headed back to recoup their fortunes in Chicago. It was too late and both died poor, Conant a mental and physical wreck. One-lung Smith lasted longer than most, operating his gambling houses for forty years. Early in the 1880s he sold his handsome establishment opposite the Palmer House and headed for New York, where he seesawed from rich to poor and died gambling with borrowed money.

Though the advent of the Illinois Central killed off the lake boats and their gambling, the railroad brought Chicago hoards that would mount to over 100,000 by 1860.

Crooked gamblers, thieves, bawds, and their pimps battened on visitors on sprees to fancy gambling houses and brothels in the city and the vile joints and hovels of the Sands. The Sands, on the North Shore, was a notorious hideout and hangout of criminals, a beehive of brothels housing the most degraded prostitutes, and a network of dens run by crooked gamblers. Strangers, enticed by ropers and pimps, were frequently robbed and killed while the police dared not venture into this criminal stronghold. Then in 1857 John Wentworth tried to cut the ulcer of the Sands from the flesh of Chicago.

As the land where the Sands stood was in litigation, no legal measures could be taken to oust its inhabitants till the court ruled or the disputants settled the question of ownership themselves. When a settlement was reached the inmates of the Sands refused to move. John W. Wentworth was the biggest mayor Chicago ever had, six feet six inches in stocking feet, and he weighed three hundred pounds. He loved a fight but he did not want to jeopardize his police, so he had the city placarded with notices of a dogfight for high stakes at the western edge of town on April 20, 1857. As he expected, practically every male citizen of the Sands turned out. Then Long John, a deputy sheriff armed with writs of eviction, a large police force, and a posse of determined citizens marched into the Sands. The madames and scarlet sisters of the nine most disreputable houses were given a few minutes to move their possessions and clear out for good. As they went Long John's men began pulling the houses down with books and chains.

The Sands recognized the handwriting on the wall and later that day occupants of shanties, saloons, and dens set fire to their buildings. The Sands was no more, but its human scum was spread through the city. The big mayor next turned his sights and leveled his guns on professional gamblers. Through his newspaper, The Democrat, he gave notice that no gambling house would stay open as long as there was an anti-gambling statute on the books and as long as he was mayor. A Chicago policeman reported the first skirmish: "On Thursday evening, July 17, 1857, one of the largest gaming houses in the city on Randolph between Clark and Dearborn Streets was raided, and 18 arrests made . . . the gamblers were one and all discharged afterward and the police became discouraged."

Despite this setback Wentworth followed up with a daytime raid. On a summer afternoon two agile policemen let themselves down from a neighboring roof into the rear windows of Dave Burrough's place, a notorious den. The windows were open and the room empty. The place was deserted except for one houseman, whom the cops took into custody along with the cash on hand. The patrons and other housemen had fled down the stairs and right into the waiting arms of a long line of police and John Wentworth. The haul was better than the mayor had dared dream: the Smith brothers themselves were captured.

Wentworth led his cohorts and their prey to the city jail in the basement of the courthouse, where he roared in a voice that carried clear to the crowds on the sidewalk that he "intended to teach them a lesson that they would remember." He saw to it that everyone caught in the raid was booked and put behind bars and declared that if anybody licensed by the city to carry on a trade or commercial enterprise showed up with bail, their licenses would be instantly voided.

The prisoners were given stiff fines before being released. They returned to Randolph Street to find that in their absence Wentworth and his police had stripped their rooms of furniture and gambling paraphernalia. Even the sporting pictures on the walls and the carpets had been confiscated. The proprietors rushed right back to the courthouse, where, before they could recover their property, they were forced to plead guilty to running gambling houses and were fined again.

Convinced that John Wentworth meant business, the gamblers closed up and gambling became almost nonexistent during his administration. Even the few small operators who opened undercover poker rooms were smoked out, arrested, fined, and forced to shut down.

When John C. Haines - whose speculations in copper were so well known his police were referred to as "coppers" - succeeded Wentworth in 1858, gamblers began to emerge from their enforced retirement. Bold men like Walter Winchester, Avery, Daniels, and John Sears took a chance on opening gambling rooms, and when they were not raided other gamblers were emboldened to follow suit.

Wentworth was re-elected in 1860, but the times were different. Chicago, as the scene of the Republican convention that nominated Lincoln and of stormy meetings about secession, was seething with sectionalism. Wentworth was kept busy seeing that rallies and parades were as peaceful as possible in these tense hours and spent much of his time conducting and speaking at pro-government meetings.

It was no year for any crusader to suppress vice in Chicago. The public was indifferent and with the Civil War lush years came to the city and the gamblers. Their establishments multiplied, as did their contempt for the law. The pattern of fleecing paymasters and bounty jumpers was repeated here on a grand scale. The '60s were a decade of skin houses and brace games. To the regular practitioners were added the Mississippi sharpers, driven off their route by the war. They generally located their hells on Randolph Street between State and Clark and along Clark to Monroe Street, and since practically every building in the district had at least one floor of rooms set up as dens of chance it was called "Gambler's Row."

The Senate, Frank Connelly's place, was the most popular resort in the Row and keno the most popular game at the Senate. Connelly believed in catering to everybody who had a dollar to risk, and keno seemed the most expeditious way to take in everybody's dollars at the same time. Eager would-be players nightly blocked the street out front, waiting to get to the tablcs. On the floor above, former riverboat gamblers dealt fancier games at fancier stakes with no shoestring players encouraged to join in. The first of the comparatively rare visits paid by the police to these elite quarters, said veteran policeman John J. Flinn, "resulted in the capture of several well-known business men, who, when arrested, were transported to the armory in carriages at Frank's expense. He afterwards paid the fines of the entire party, and immediately opened his house as though nothing had occurred to disturb the serenity of the situation."

Such few raids as were held up to 1871, when Joseph Medill came in as mayor, were ridiculed by gamblers, one of whom said that they "appeared to be conducted not so much with a view of suppressing vice or injuring the business of the houses raided, as for the purpose of raising a sort of indirect tax, or levying an illegal assessment. No one ever thought of destroying personal property found in the resorts, and the fines imposed were usually very light. In fact, so little attention was paid to them that the proprietors were wont to admit the officers with the utmost cheerfulness; and when a `hell' was pulled hacks were at once called into requisition and the dealers and players rode together to the office of the nearest police magistrate, where bail was at once accepted, and the party again entering their carriages, returned to the rooms and resumed play."

To Theodore Cameron's gambling house at the northeast corner of Clark and Madison streets, lib steerers brought well heeled victims to play against men like Fred White, one of the cleverest card manipulators of the day. White so swelled the house profits that Cameron was able to open a posh gambling hell at 68 Randolph Street. Aside from the usual luxuries there were comfortable rooms where customers, exhausted by strenuous hours of play, could retire till they were rested enough to get back to the tables.

The gambling fraternity called this a "bird house" and the wise ones stayed away. Number 68 was for the suckers and it was crooked all the way. But to ease the suckers' pain, Cameron's partner, "Dr." Ladd, made it his business to see that the sideboard was never empty. It was a costly business, but the "fat" suckers paid so high that Cameron became the prince of spenders in Chicago's demimonde.

He was not the only royalty in Chicago. Mike McDonald had already become "King" Mike by 1875, when he opened the Store on Clark Street. McDonald was only twenty-two when the Civil War broke out, but he had three years as a professional gambler behind him in the dens of Gambler's Row. The future boss politician's name was prominent among signers of a call for the formation of Mulligan's Civil War Brigade, to be composed of loyal Irish volunteers living in Chicago. NIcDonald assumed the rank of colonel but never actually joined the brigade or left Gambler's Row during the conflict, by the end of which he was rich and well known as a gambler.

Pickings were excellent, but still there was competition. Ropers would station themselves in hallways of rival establishments and at the sound of an approaching sucker turn off the gaslight and maintain regretfully that the house was closed for the night. From here on it was easy to get the chump to their own den, where they invariably braced him out of his money.

Pickings, indeed, were so excellent that "Chicago was soon filled with a set of sharpers drawn from all quarters of the United States," John Quinn noted, "comprising as motley, disreputable and dishonest a class as ever cursed any city under the face of Heaven. Wealthy `suckers' were found in abundance, and `brace' dealers, `bunko' men and rogues of every description carried off money in bundles."

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