Spending a Night in Shaker’s Haunted Penthouse

Oct. 18, 2016
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My life experience with ghosts and the paranormal world is incredibly limited. To say I’m skeptical of the existence of ghosts would be an understatement. But when the opportunity to take the “Ghost Tour” and stay a night in the haunted penthouse at Shaker’s Cigar Bar was presented to me I was intrigued and hopeful of being surprised by a frightening otherworldly experience. 

When I arrived at Shaker’s around 8:30 p.m. for the tour I was calm and composed. I had read some reviews online and heard things from friends, some telling stories of their ghostly encounters and others sharing my skeptical point of view.

To quell the minimal amount of nerves that had started to creep in, I grabbed a drink from the bar. Aside from the ghost stories and cigars, Shaker’s is well known for their extensive whiskey selection and cocktails. 

The tour began outside with the painting of “Molly,” the establishment’s most famous apparition. The guide took us around the exterior of the building and explained that during prohibition the bar was operated by Al Capone and his crime family as a speakeasy and brothel. The guide talked about the history of the neighborhood, along with the inherent danger of Milwaukee in that era.

As we went inside, the guide pointed out the first especially haunted space in the building, the women’s bathroom, which is said to be haunted by the spirit of a young girl who died in the building during the Capone days. Hearing the girl’s story, and the surrounding details of ensuing events such as a photo disappearing multiple times, brought upon a slight touch of anxiety.

After hearing about the young girl, we looked at a few photos, which had supposedly changed over the years, with people growing horns and other’s feet growing to unnatural lengths. Of all of the supernatural activity presented on the tour, I found these photographs to be the most easily dismissed.

The next step on the tour was the basement. I find most basements to be a bit off-putting, even minus the threat of ghosts tugging at your hair and pushing you from behind. They’re dark, unfinished and uninviting. When you add stories of confederate soldiers, who continue to move an extremely heavy safe around, murdered mobsters who can be seen in photos taken where they were buried and “shadow people,” whatever that means, my blood pressure began to rise higher than my skeptical brain had expected.

After walking through and hearing stories of what had happened in the basement, we took a brief intermission for more cocktails or visits to the haunted bathrooms. When the group came back together, we were directed up the stairs, which housed the brothel portion of Capone’s business, and is said to be the most spirit-filled area of the building.

The ambiance on the second floor is intentionally made to be eerie- with dim, colored lights skewing the vision of tour-goers, creepy photos and a hog's head hanging from the wall. The guide pointed out a door that remains locked and inaccessible, and has not been opened in years. Although I’m sure that’s just something they say on the tour, it still adds another layer of mystique to the tour.

As we made it to the top floor- the penthouse in which I would be spending the night- I began to question what I was getting myself into. From a logical perspective, I was still completely unconvinced that spirits were around to interact with the living, but the grim setting and unsettling ghost stories were beginning to diminish my rational resolve. 

As we continued through the ominous upstairs lobby, the guide told the story of Molly, who was the “A-girl” (prohibition-era slang for most popular prostitute in the brothel) and lived in the penthouse full-time. He talked about what day-to-day life was like in the brothel, and how someone would have to sponsor Molly to live there.

What followed was the point in the tour where my resolve was most flinching. He told the story of the brutal murder of Molly, committed by not only a regular of the brother, but a trusted childhood friend named Patrick, who was then murdered by someone likely affiliated with the Capone gang.

These brutal crimes have led to both of their spirits making the penthouse their permanent home, though Molly is much more interactive with visitors than Patrick is. The phenomenon was demonstrated, much to my dismay, through the use of dowsing rods, which are metal rods supposedly used to connect with the dead. At this point, I was considering going home after the tour and never coming back.

The tour ended around 9:30 p.m. and the rest of the group headed home to their safe un-haunted houses, while I awaited my night in the penthouse. I was told I wouldn’t be able to access the my room until midnight, which meant I could continue to explore the list of whiskeys and smoke a cigar to quell my anxieties for a couple of hours before meeting Molly. The bartender recommended to me a drink made with absinthe, champagne and bitters, which was phenomenal.

I spent some time acquainting myself with the staff, which was all charismatic and knowledgeable. They told me their own stories of spirit interactions, which involved such things as hair pulling, hearing doors slam when there was no one else around.

One staff member told a specifically troubling story of a mother fearfully telling her daughter to leave the red room she was in (Molly’s bedroom), even though she had no prior knowledge of her daughter being on the tour. It was interesting to hear the perspectives of a group of people who have chosen to work in a place they believe, or at least convincingly pretend to believe, is inhabited with dark spirits.

Was I skeptical that these were all stories made up to scare me? Of course, but nonetheless I was at the same time entertained and anxious. 

When midnight came I was ready to go to bed. My anxieties about the experience had grown incrementally throughout the night, but I had accepted that nothing bad could possibly happen. 

While I did truly believe this, I was still nervous as I walked up the steps and entered the apartment. Though I was tired, I didn’t want to just fall asleep right away so I walked around and took in whatever the room had to offer.

After, about 45 minutes of walking through the apartment, taking photos and thinking about all of the things that have (or may have) happened in these rooms over the years, I was ready to climb into bed and drift off to sleep.

Thankfully, I awoke in the morning, with everything in the same place as I had left it (I was told Molly likes to move shoes into the sink in the middle of the night).

Having lived to tell the tale of the tour, I don’t personally believe that Shaker’s is actually haunted. Psychologically, I believe that if you have the temperament or inclination, it’s possible to convince yourself of anything, and that is how people experience paranormal encounters. Even if Shaker’s isn’t filled with spirits trying to put my shoes in the sink, it is filled with the fascinatingly sordid history of prohibition-era Milwaukee, and knowledgeable people who are able to retell the story of the Walker’s Point that existed long before it become filled with your favorite restaurants and bars.

Who knows, you may just be one of the “lucky” ones who has a real ghost experience. 

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