Downtown Milwaukee in 1857, when gamblers and city fathers were one in the same. (Wikicommons)
Just as with prostitution, murder, and complaints about the weather, games of chance have been a part of Milwaukee as far back as the city has existed. While reformers cried for local officials to chase illicit gambling from Milwaukee in the 1890s, the decades prior saw little official objection to the practice. Indeed, many of the city’s wealthiest and most prominent men were known patrons of Milwaukee’s numerous gambling halls. Other men were so known on the scene that their gaming exploits earned them their own kind of local celebrity.
While no Milwaukee gambling hall matched this unidentified Monte Carlo gaming parlor, the city’s highest-stakes halls were patronized by some of early Milwaukee’s most prominent men.
Illicit gaming among the Europeans first appeared in the area during Milwaukee’s pioneer days. Men working in the southern Wisconsin lead mining trade migrated to the city with money to burn. Among these was a man named Ninian Whitesides, who saw the way his fellow miners blew through their cash on whiskey, women, and card games. Whitesides set himself up in a downtown gambling hall and became one of the city’s most popular hosts of the French card game “faro,” a favorite of the miners. Whitesides’ “dealing” skills seemed to carry over into the political realm as well. In 1846, he helped to write the state constitution and later served in the state territorial council. In 1848, he was elected to the very first Wisconsin State Assembly and served as the state’s first-ever Speaker of the House. After he left Wisconsin to join the California Gold Rush, he was also elected to the California State Assembly and eventually became its Speaker of the House. He had two brothers who were also practiced in gambling and politics, but lacked Ninian’s lucky streak. One brother, Buck, died in California after being bitten by a diseased sheep. Another brother, Wash, shot a man over a game of poker during a session of the Illinois legislature.
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If the mix of illegal gambling and civic service seems odd today, it raised little ire back in the days of the Whitesides brothers. “Men whose names have since become as inseparably connected with the history of Milwaukee and Wisconsin as those of the Pilgrim fathers with the founding of Massachusetts,” the Milwaukee Journal wrote in 1895, “were [known gamblers] then and they apparently lost none of the esteem of the community on that account.” The difference between the pioneer man who could indulge without censure of his peers and the man who was seen a degenerate gambler, the paper noted, was only in the former’s knowing when to walk away from the table. To be a gambler was nothing to be ashamed of. To be an addict to the game was an entirely different matter.
Thomas Wickes, who ran one of early Milwaukee’s highest-stakes card games.
Of course, losing big did not always mean losing everything. A secret cadre of local businessmen – the “wealthiest and most influential in the city” per the Journal – partook in regular card games in the 1880s with a buy-in of $1,000 cash. The gambling den of Thomas Wickes, located just east of the river on what is now Wisconsin Avenue, sometimes extended lines of credit into the several thousand dollars to regular customers who were know to be “good for it.” Wickes himself was a prominent local politician, arriving in Wisconsin in 1855 and opening a low-end gambling hall in Madison. He entered into politics only when a troublesome foe of illicit gaming opened up a crusade against his hall. While he never held office himself, his money and influence, both in Madison and Milwaukee, earned him a long list of elected allies, each of whom were bound to put any talk of running gamblers out of town.
While Wickes built his political empire, Charley Sholes, keeper of a regal downtown gambling hall on Broadway, was born into one. Charley was the son of Christopher Latham Sholes, newspaper publisher, member of both the state senate and assembly, and inventor of the QWERTY typewriter. Charley’s uncle, also named Charles, was also a newspaper publisher and prominent Wisconsin politician. Young Charley also had an appetite for glad-handing and gossip, but preferred to operate on the other side of the law. His place – located above the Marble Hall, just a few doors to the north of the Newhall House hotel – was a regular stop for members of many of the nation’s most prominent families and nearly every Milwaukee man of high standing in business or politics. On Thanksgiving and Christmas, he enticed these men out of the family home with fine turkey dinners and free cigars.
The Marble Hall, where some of Milwaukee’s most respected citizens engaged in after-hours gaming. Wisconsin News, January 19, 1933.
Far rarer than the men of prominence who became known in gambling circles were the men who made their name on gambling alone and managed to play alongside the city’s most respected citizens without having a title or position to boost their reputations. Russell Wheeler was one of the city’s most famous gamblers and was said to be unafraid to play stakes as rich as many city father or bank president. Wheeler was open to less-than-honest means to help secure his often enormous winnings and one evening in 1878 lured a local card shark named Ted Henderer into a crooked card game and took him for thousands. Henderer suspected he had been duped and carried a grudge against Wheeler for months until the two ran into each other one night in a downtown barroom. After a brief quarrel, Wheeler shot Henderer through the heart, killing him instantly. He was charged with manslaughter but, being regarded favorably by most citizens, was acquitted.
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Also profiting from shady card-handling was “Old Ed” Simpson, Milwaukee’s most devious host of three card monte and the hidden ball “shell game.” Per the Journal, Old Ed was “one of the sharpest men that ever disappointed a deluded rustic who imaged that the trick of picking the ace in a three card game was easy.” He worked out of Milwaukee, but traveled the backroads in the summertime, hitting country fairs and small town picnics where the local rubes wasted no time in passing over their coins. He was said to be able to earn $1,500 in a single town without even needing to rent a room. But the old adage that the house always wins somehow never stuck with Old Ed. He burned through his money as fast as he earned it, enjoying a place among the high stakes men of the city, but lacking their skill at card-playing almost entirely.
The era of Milwaukee’s wide-open gambling scene came to an end in the mid 1890s as a group of local Reverends began to press the police for action against the “sinful” practice. By then, many of the big name old-timers had mostly all either died or gotten out of the game, and the new stringent attitude forced by the Reverends made the city’s new wave of gambling big shots much more anonymous than they had been in generations before. Of course, men of means still did as they pleased, but now the police were required to at least pretend to care.
