Tavern Owner Plans Northwest Side Location
New bar and restaurant, Boss's, would replace Douglas Inn.
6180 N. 64th St. Photo taken Jan. 7, 2026 by Mary Bolich.
A new bar and restaurant, Boss’s, is slated to open later this winter at 6180 N. 64th St. Justin Jackson recently filed a license application for the location, which is currently home to the Douglas Inn.
Jackson, who also owns Champs Trucking, LLC and the nearby New Entertainers bar, purchased the 3,424-square-foot tavern building in November 2025 and plans to take over the business “as soon as possible,” according to the application.
Under Jackson’s leadership, the neighborhood bar would continue as a destination for alcoholic beverages and entertainment, also expanding to include a casual food program.
A proposed menu features pub fare like pizza, chicken, tacos, burgers and sandwiches, plus heartier entrees such as steak and pork chops. Shareable appetizers and sides could include mozzarella sticks, onion rings, fries and bacon.
Daily specials like Taco Tuesday, 50-cent Wing Wednesday and Ladies Night Thursday are also listed, along with recurring deals like free hookah on Mondays and a $25 “drink all night” wristband promotion.
The menu warns customers of a zero-tolerance policy for attitude and violence, and advises: “We don’t rush for those who aren’t tipping.”
A floor plan submitted with the application includes wraparound bar seating and more than a dozen booths and tables throughout the tavern space. A back corner is designated as a gaming area, with plans for a dart board and three amusement machines, pending city approval.
Jackson has also requested permission to host DJs and offer hookah service, but said he doesn’t plan to use promoters or sound amplification.
The northwest-side building neighbors Imperial Flavors Beverage Co. and The Hangar, headquarters for Wauwatosa-Milwaukee Little League. The nearest residential property is located approximately one block away.
A license application for Boss’s is pending before the Milwaukee Common Council. If approved, the business’s proposed hours of operation are Monday through Thursday from noon to 2 a.m., Friday and Saturday from noon to 2:30 a.m. and Sunday from 2 p.m. to 2 a.m.
Jackson did not respond to a request for comment by the time of publication.
His other business, New Entertainers, is facing a 30-day suspension from the City of Milwaukee following a Jan. 6 Licenses Committee hearing. The tavern, also known as Regal Begal, was last disciplined in 2024, and was required to close for more than two weeks.
Council members are set to vote on the latest suspension on Jan. 20.
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