Back to Notorious Chicago
The center of the gambling industry, which was illegal but well protected through heavy payments to the police, was on Randolph and Clark Streets, which contained palatial “skinning houses” for trimming the suckers. Naturally, with fortunes won and lost so easily, shootings and killings were common and probably far more frequent than could be found in any town of the Wild West. In fact, Randolph Street between Clark and State was commonly referred to as Hairtrigger Block because of the many shootings that took place there. A local newspaper wrote that this area had “become so contaminated by these execrable vagabonds that respectable persons avoid them as they would a cesspool.”
Intersection of Clark and Randolph Streets
Some of the shootings were between professional gamblers themselves over matters such as possession of a “mark” or out of just plain nastiness. The most famous feud on Hairtrigger Block was between two big gamblers, George Trussell, the dandy of Gambler’s Row, and Cap Hyman, described as “an insufferable egotist, an excitable, emotional jack-in-the-box.” They could barely tolerate each other when sober, but when drunk they would immediately start shooting at each other; each probably shot at and was shot at by the other at least 50 times. Both, especially when intoxicated, were incredibly bad marksmen, and the usual damage was to windows, bar mirrors and street signs. So long as the shooting was confined to Hairtrigger Block, the police did not intervene; unfortunately, the two gamblers often staggered off to other areas in search of each other and continued their shooting sprees, leading the Chicago Tribune to declare that “the practice is becoming altogether too prevalent in this city.” Hyman was frequently arrested and fined for his forays, and after paying the penalty, he would meticulously deduct the amount from his usual police payoffs. Whenever a Trussell-Hyman duel started, the inhabitants and habitués of Hairtrigger Block immediately wagered on which one would be killed.
As it turned out, neither of the two ever prevailed over the other. Trussell was shot to death by his mistress in 1866, and Hyman went insane and died in 1876.
Cap Hyman ran his own card house at 81 W. Randolph. Hyman’s mistress was “Gentle” Annie Stafford, who had recently removed from The Sands, a lowlife resort which was located where the Tribune building now stands on N. Michigan Ave., but had recently been forced to open a new establishment at 155 N. Wells. On September 23, 1866, Gentle Annie, armed with a rawhide whip, stormed into Hyman’s gambling den, dragged him out, knocked him downstairs, and chased him up Wells street. A few weeks later, Cap and Annie were legally married at a wedding attended by the cream of the underworld crop, not only from Chicago, but from St. Louis, Cincinnati, New Orleans, and Louisville.
Clark and Belmont
In late 1866, Hyman and his wife, Annie Stafford, had opened to the public their Sunnyside Resort in Lake View, a roadside inn on Clark Street near Montrose.
The grand opening was on a Wednesday evening in December, 1866, and reporters from the major Chicago papers were brought to the gala affair in a huge four-horse sleigh. Hyman declared to all, “I would like you gentlemen of the press to understand that this affair will be straight to the wink of an eyelash. All the ladies are here on their honor, and Mrs. Hyman will see to it that nothing unseemly takes place.”
Nevertheless, opening night was portentous. Hyman and Stafford intended the Resort to cater primarily to the well-to-do country traveler, and to stand as their entree into Chicago’s upper crust society. But all of the couple’s friends were from a distinctly different social class. A newspaper article at the time described the opening night guest list: “the list was select, embracing chiefly the women keepers of some of the more fashionable brothels, and those who contribute most liberally to their support.”
Everything went swimmingly until around midnight, when a fight broke out among three rival cyprians at the party, which turned into an all-out wrestling match. In a drunken fit, Hyman shot out the lights, and several of the harlots began “entertaining” clients upstairs. By dawn, the evening’s tired and mangled party guests departed, and the bad publicity associated with the evening’s melee doomed the business; it shut down to the public within six months.
Gentle Annie continued running a South-side brothel until 1880.