Day 236: The Ghosts Of Omaha’s Dark Past

originally published August 23, 2012

When I was a young, struggling writer, someone told me to write what I know. It turned out I knew almost nothing about anything, and my writing aptly reflected that. Now that I have matured into an old, struggling writer, I prefer the approach of writing whatever the hell interests me.

I have never been to Omaha. In fact, I’ve never been to Nebraska, nor do I see that happening in my future. Even if I needed to drive to Kansas for some reason, I’d probably swoop through Colorado instead; they have about 2000 breweries in that state, and I’ve got to follow the attractions that interest me.

Omaha in the 1800s is an intriguing subject, because the town was ripe with corruption, crime, gambling, whoring, and relative lawlessness. If you’re looking to relocate to a place where every day is an adventure, I strongly recommend moving to Omaha in the 1800s. Also, real estate would be cheap.

A town like Omaha, one which runs on vitriol and the foul stench of greed, is inevitably populated by a colorful slather of interesting people. One such fellow was noted gambler Dan Allen.

Dan wasn’t known for any particular skill, nor was he seen as a degenerate cheat, though Omaha’s complicit embrace of gambling and prostitution invited a score of dishonest bloodsuckers to take advantage of the rubes within the city limits. Dan was an honest gambler. He ran a gambling hall in the area known as the Sporting District. He also ran a pawn shop.

Specifically, Dan ran his gambling hall one floor up from his pawn shop. It was an early demonstration of business synergy. When a client upstairs ran afoul of Lady Luck and found himself with nothing more than lint in his pockets, he could step over the dumbwaiter in the wall, lower his watch, rings, or gold-plated walking sticks down to the pawn shop, where a helpful attendant would receive the goods and send the money back up.

It was a perfect system.

One man who never sought to match Dan in the scruples department was Canada Bill Jones.

“It’s immoral to let a sucker keep his money.” That’s a quote from Canada Bill, and it neatly sums up his approach to his trade. Bill’s game was three-card-monte. Three-card-monte is not a game a gambler opts to perfect in order to out-perform competitors from behind a dark pair of sunglasses in a quiet room, surrounded by a studio audience and inexplicably broadcast on ESPN. Three-card-monte is a game you learn for the sole purpose of scamming other humans.

Canada Bill was quite good at this. Along with his partner, Dutch Charlie (and never a better gambler’s name have I heard), Canada Bill wandered into Omaha after the Civil War. His turf was the Union Pacific train between Omaha and Kansas City, where a fresh crop of dopes could always be counted upon to evict their money from their pockets into Canada Bill’s eager hands. When the management at Union-Pacific respectfully insisted that Bill and Charlie take their game elsewhere, Canada Bill sent a note to the superintendent, offering a cut of $10,000 per year if they could stay on the trains. That didn’t happen.

Like Dan Allen, Bill was an entrepreneur. He had a fleet of three-card-monte sharks working for him in Omaha. It was an easy score – Omaha’s police department in the post-Civil War years was little more than a joke. The twelve (yes, twelve) police officers employed by the city could often be counted upon to ditch their beat at midnight to attend dances at the Old Bohemian Hall. When a group of lawmen smaller than the cast of Hill Street Blues is assigned to police a city the size of Omaha (roughly 16,000 citizens), corners will have to be cut.

Canada Bill’s shtick involved some intense thespian work. He’d pretend to be a farmer, a merchant, maybe a lawyer. He’d present himself as someone out of their element, trying to make some money through a trade he hadn’t quite mastered yet. Then he’d bleed his mark dry with a swift gust of “luck”. Residents finally decided they’d had enough of Canada Bill, and he moved on to his next market crop of rubes in 1876.

Elsewhere in the city, illicit business continued to boom. Savvy guests at local hotels often found themselves escorted into secret tunnels under the hotel grounds. Those tunnels would lead them into Omaha’s most prized underworld: the brothels.

Omaha madams had a reputation as some of the city’s most esteemed citizens. Mae Hogan picked up the tab for the indigents at St. Joseph hospital. She cared for orphaned street urchins. Of course the history books don’t dwell on the fact that the vaginas belonging to those urchins probably made their way into Mae Hogan’s employ. That’s okay, let’s focus on the positive.

One bestn’t speak of debauchery in Omaha without paying tribute to the Queen of the Underworld, Anna Wilson.

Wilson ran Omaha’s most successful brothel for about 40 years. She also had a reputation for generosity, standing in as a parent and picking up the tab whenever one of her girls got married. Her long-time romantic companion was none other than Dan Allen, proprietor of the one-stop hock-n-play pawn shop/gambling hall down the road. When Dan passed away in 1884, Anna Wilson spent a fortune ensuring his grave would be perpetually covered in fresh flowers for the remainder of her days.

After Dan’s departure, Anna built the 25-room mansion pictured above. Inside its walls she ran the most impressive brothel Omaha had ever seen. She also made several real estate investments, and at the time of her death it was reported that she was worth more than a million dollars.

Anna had no family though, so her fortune was willed to the city. In 1910, she donated her mansion to a more ‘legit’ purpose; it became the Omaha Emergency Hospital. The facility operated until the 1940s when it was torn down and paved into a parking lot.

Again, no photo of Anna exists (at least not online, and nothing exists unless it’s online nowadays). All we have is this:

Both Dan Allen and Anna Wilson are buried in this grave in Prospect Hill Cemetery. Anna had insisted upon nine feet of concrete between the bodies and the grass, just in case any society women decided to exact revenge on Wilson’s unchristian life by defiling her corpse. Technology has come a long way since then though, and renting equipment to ramble through nine feet of concrete is as easy as a trip to your local Home Depot. So have at it, Christian ladies!

The Prospect Hill Preservation Society celebrates Anna Wilson every Memorial Day with a concert of Dixieland music and a tribute to her life. I like that. Las Vegas was built by criminals, New York’s mafia history is the stuff of legend, but you don’t often hear about a city that honors the non-law-abiding citizens who helped to shape its personality. Kudos, Omaha. You sound like a cool place.

Too bad I probably won’t ever visit.

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