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Ghost Tour in One of the Most Haunted Bars in America

While in Milwaukee for a conference, I took a friend’s recommendation to stop in Shaker’s Cigar Bar for a drink….and a ghost tour. As I left some conference friends, one of them said, ‘don’t bring anything or anyone back with you!” I laughed but that started my nervousness of what I might encounter that evening.

Walk in the bar and you instantly get a speakeasy vibe. The bar is in Walker’s Point, a cultural and foodie hotspot in a historically diverse neighborhood of historic and industrial buildings. Shaker’s opened in 1986, but the building’s history extends way before then. In 1894 it was built over one of three original cemeteries in the area. It was a Schlitz Brewery cooperage in the late 1800s and early 1900s and was a speakeasy and brothel owned by the Capone brothers during Prohibition. Shaker’s is known for three things: cigars, spirits, and encounters with those who never left. The cognac dates back to 1879, but I opted for a light French 75 cocktail while dining on the calamari special. Both were fabulous by the way. My nervous chatter was quite obvious I’m sure as I chatted with Bob Weiss, the owner of Shaker’s, and one of his long-time buddies. I got the backstory on the building and some of its patrons, including serial killer Jeffrey Dahmer was an occasional patron in 1991 from January to July, when he was arrested. Well, that threw a whole different level of bizarreness to my spirited evening.

Before the tour, I went to the women’s restaurant, hoping to encounter my first ghost. Apparently there is a little girl who haunts the space. Her name is Elizabeth and her death pre-dates the building. When it was most likely a cemetery, the 8-9 year old girl climbed up an apple tree in 1835, fell and broke her neck. She’s often heard laughing, moving things or pulling tricks in the bathroom area. A friendly prankster is my kind of ghost! I went into the bathroom, said her name, looked around for anything unusual and went into the stall. When I unlocked the stall door and tried to leave, it would budge. Took me three pushes for it to finally open. Stuck hinge? Elizabeth the prankster ghost? I chose to believe the later. I returned to the table nervously laughing, down a second French 75 and hoped that would be my only encounter on the tour.

My Shaker’s Ghost Tour guide was Melanie. She was a delight – very engaging, funny and full of ghostly tales. We started the tour in the alley to enter through the Prohibition entrance. From 1922 to 1946 Al and Frank Capone owned the building operating a soda bottling area in the front, speakeasy in the back and brothel upstairs. While standing in the speakeasy area (now back dining room area), Melanie pointed out the archway dividing the two large rooms on the first floor. The front was where they bottled soda during Prohibition and the back where we were standing was where men induldged in drinks and smokes while being tantalized by sexual engagements with ladies. From the Juliette balcony on the back wall, above where were entered, ladies would “advertise.” The long bar in the back is original and so are the arches and metal tin ceiling.

Melanie went on to tell the story of Elizabeth to the rest of the tour group made up of a birthday party group and a couple. Then we went into the basement. I was the last one to head down, or so I thought. I closed the door and stood at the top of the stairs to take pictures and video. As I was about to walk down, something caught my eye. General Manager Brianna scared me half to death by accident. She had silently entered behind me while I was filming. Yes, I screamed then laughed. In the basement Melanie elaborated on the story of the land. It was one of three non-indigenous cemeteries. Sometimes folks see shadow people and even a shadow cat. As Melanie said, “You’re never alone down here.” In the eerie darkness I felt extremely uneasy to the point of really creeped out feeling like I was being watched in the stifled air of the basement. In a small nook off the hallway, there’s a cistern. I looked at it and kept on moving as cisterns are sometime considered portals to evil. In that hallway there’s also a large railroad safe. It’s lead and has never been opened, even after multiple tries. Melanie’s reason for why the safe can’t be open was, “I think there’s nothing in there but bad vibes.” If that’s the case – keep it closed! In the back room you can’t help but notice two skeletons laying on the floor. On a close inspection, you’ll notice a rectangular section of cement is slightly different. Melanie said investigators determined there were two bodies in the cement from the Capone ownership time. It’s likely two politicians from Chicago. She also told us the story of O’Connor, a confederate soldier who was from Milwaukee. The Irishman has a thing for redheads and blondes and can get touchy feely. The last thing we saw in the basement was a staircase to nowhere. It goes into a brick wall.

I think the whole tour group was ready was to get out of the dark basement when we headed up to the second floor. We made a detour for a bathroom and cocktail break. I took more pictures and videos on the main floor, only to realize later those mysteriously weren’t on my phone, even though I checked right after I took them. Melanie told me that sometimes happens. Chalk it up to ghost interference I guess. During its brothel days during Prohibition this floor was the “B” floor. The lobby was also known as the “fluffer” room where patrons were prepped for their rendezvous. The third floor was the “A” floor where Capone’s best money makers performed their services for the high rolling clients. Most the of girls in the brothel were girls between 14-18 years old. There were 6-8 girls on the “B” floor. Once they aged out, they typically went on to a nunnery or to the streets. There was a doctor’s office on the “B” floor. One the “A” floor there was typicall 1-3 girls. Those girls typically had sponsors. A favorite “A” girl was 16-year-old Molly Brennan involved in a tragic love scuffle. As Melanie told the story, it went something like this. Molly was involved with Patrick, a wealthy gentleman. On the way up to the brothel, he passed Sam, the bouncer. Upstairs Patrick found Molly with her sponsor, Harvey, who was Patrick’s dad. There was a struggle and allegedly Patrick strangled Molly. Sam and Patrick were also found dead, but who killed who is muttled. In 2001 while the bar was undergoing some renovations, bones were found under some floorboards in the penthouse. A medical examiner determined some were animal bones and some were human bones at least 70 years old, which would date them back to around the 1920s and could be those of Molly Brennan. The penthouse is now an Airbnb. Most people don’t make it through the night.

We had a little extra time on our tour and headed to the rooftop for a great view of city including stained glass water tower. It was about 10pm when we walked back down to the main floor and I decided even with liquid courage from Shaker’s Cigar Bar spirits, there’s no way I’m spending the night with prostitute ghost! But, I’d happily return to Shaker’s for drinks, food and more ghost stories.

Jennifer Broome went to Shaker’s while in Milwaukee for the first time. Check out blog on the Saint Kate as a Hot Spots to Stay and Canary Coffee for a Travel Taste read.