"Cap" Hyman's Sunnyside Resort

Captain "Cap" Hyman was one of Chicago's most infamous characters before the Great Fire. An inveterate gambler, he was one of the kings of "Hairtrigger Block", a gambling mecca on Randolph St., west of State.

Hairtrigger is a word that also describes Hyman's personal character. In an inebriated state, he was well-known in the city for wandering into public places and brandishing his pistol. In 1862, he did just that in the Tremont House hotel.

On the evening of August 2, 1868, around midnight, Cap Hyman found himself at the New York Sample Room, a low saloon in Clark Street. The following day's Tribune detailed what happened next:

[Hyman] entered the saloon about midnight, meeting at the entrance a friend named James McKenna, barkeeper at the Sherman House. He invited him to drink and the two, accompanied by others, stepped up to the bar. A dispute arose between them as to who should "treat," when McKenna spiritedly accused his companion of owing a bill for liquor, etc., at the Sherman House. Hyman stepped from the barroom, which is in the rear portio of the place, to the front compartment, and, drawing a revolver, discharged it at McKenna. The contents, probably a blank cartridge, failed to do any injury. He fired again, the ball entering the groin of M. Kasprowicz, inflicting a serious but not very dangerous wound. At latest accounts the victim was doing well.

Kasprowicz, also a noted gambler, was also the son of the saloon's proprietor. The article referred to both Hyman and Kasprowicz as "[g]amblers of the worst kind and very dangerous members of society." A police search for Hyman the next day failed to find him, but eventually he turned himself in, and after lengthy legal maneuvering, he was released back into the city to create more mayhem.

During his time on the lam for the Kasprowicz shooting, Hyman laid low at his place in suburban Lake View, which was in the 1860s farmland not incorporated into Chicago. Two years earlier, in 1866, Hyman and his wife, the fat brothel-keeper and former Sands resident, Annie Stafford, had opened to the public their Sunnyside Resort in Lake View, a roadside inn on the old Evanston Road (now Broadway) near the intersection with eponymous street, Sunnyside Ave. (pictured above).

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: "[t]he 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.

Hyman and Stafford continued to make trouble in Chicago for a few more years before they separated, with the Captain heading to New York in 1868. Rumor had it that the old gambler's mental health was not good, perhaps the result of too many evenings spent in brothels like Annie Stafford's. In possibly the most sarcastic editorial ever published in the Tribune, the paper wrote of news of Hyman's decline:

Report has just reached Chicago of the fall of a great man. As a gambler he stood at the head of his profession, in braggadocio he had not his equal, and as a shooter at defenceless cripples and women he stood without a rival. Of course, this means the Adonis, Captain Hyman. How his diamonds used to flash in the sunlight of our streets! With what elegance of deportment he used to pick his teeth on the steps of our hotels! How immaculate was wont to be his toilet! But, alas! he left Chicago about a year ago, and with it has come his fall. Detective Ellis, just returned from New York, met him in the great metropolis, and at first mistook him for a peddler of "hot corn." The change seemed incredible. Not even a brass band ornamented his nimble digits, and he looked as if he had not enjoyed a square meal for a week. In other words, the whilom proprietor of sumptuous Sunnyside and the hero of innumerable bouts is broke clear out of his boots. Wonder if he will ever "come up smiling" again?"

Suffice it to say Cap Hyman was not a popular figure in Chicago, and his demise in the mid-1870s was welcomed by all. Annie Stafford continued to run brothels on Federal St. (then Fourth Ave.) and Wells Street until about 1880.

Accounts published in the 1860s put the location of the Sunnyside Resort on the Evanston Road (Broadway) "about two or three miles from the city limit", at what is now Sunnyside Ave. Based on educated guesses from other sources, I believe the Southeast corner of Broadway and Sunnyside would have been the most likely location for the Resort. This is pictured above.

A later account in 1941 by an old-timer describes a place called the Sunnyside Tavern, where Chicagoans of the 1880s used to go out sledding in the wintertime on Clark Street at Sunnyside. Since Clark is just west of Broadway at this point, it's possible this is the same establishment (perhaps under the control of a later owner), but I cannot corroborate that. Also, in Gem of the Prairie, published in 1940, Herbert Asbury also puts the location of Hyman's Resort on Clark St., possibly based on the same source. Nevertheless, I have chosen to rely on the contemporaneous accounts.

In any case, the Resort was gone by the turn of the century, and the southeast corner of Broadway and Sunnyside became the site of a dull gray three-story building, which was razed in 1929 and rebuilt as an equally dull gray three-story building (pictured above), inhabited by administrative offices of the Illinois Bell company. In the 1950s, Illinois Bell quit the building, which then became the offices of the city's Department of Urban Renewal. By the 1970s, the building was under the control of the Salvation Army, which ran it as a soup kitchen and shelter through the 1980s and 1990s. It appears to be closed now, possibly slated for destruction along with the buildings across from it on Broadway, which have already fallen, to be replaced by a Target.