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There was a time when Jim’s Time Out, 746 N. James Lovell St., was a place I visited frequently. It was a nice, quiet neighborhood bar, hidden right in the heart of Westown.
About seven years ago, under new ownership, the bar got a makeover and, later, a name change. Since then, it’s been called Stella’s: A Cocktail Dive Bar, in honor of a long-serving bartender, now retired.
Occupying a 19th century former residence that was extended out toward the sidewalk to create a retail, restaurant and then tavern space, Stella’s has managed to change and yet feel as if it has, more or less, stayed the same.
After serving as a restaurant in the 1940s – a classified ad in ‘48 described it as such – a 1949 real estate ad offered it for sale as a tavern.
By the mid-1950s, it was home to the Ding Dong Bar (which may or may not have been related to the Ding Dong that was at 1566 S. Muskego Ave. in 1939 or the 1941 Ding Dong Bar location at 436 W. Kilbourn), operated by Mrs. Susan Bakos.
By 1971 it was for sale again, though as late as 1982 it still had the Ding Dong name.
But not long afterward, Jim Pappas was behind the pine and Jim’s Time Out was born.
It was a place where you went for a cheap PBR, Schlitz or High Life, maybe a shot of Jack, and by the time I was frequenting it in the early 1990s, it had the feel of an early ‘80s bar off Times Square in New York City.
You might find a couple lawyers who’d stopped in for a cold one after work at the nearby courthouse, maybe a few Milwaukee Public Museum exhibit builders having a laugh, some down on their luck folks at opposite ends of the bar, and a sparse but steady parade of folks popping in to cadge a cigarette or use the bathrooms.
Jim’s was not fancy. It was a downtown dive bar, but in the best Wisconsin sense of the word. It was friendly enough, quiet (generally), dark, inexpensive.
When the current owners – Steve Gilberston, Jay Stamates and Sam Berman (names you might recognize from their other bars: Sabbatic, The Standard, Tin Widow) – bought it in 2013 they didn’t change anything.
But there was more than tradition behind that decision.
“When we came in it had a clientele,” Stamates recalls. “The problem with doing any sort of facelift or putting any money into it was that it was directly adjacent to a condemned parking garage. We didn't want to put any money into it, because we didn't know if the city was going to call eminent domain and scoop (our building) up for a municipal building or something.
“So we just sat back; it was making a little bit of money. Jim did a great job setting it up for success.”
When that concrete garage out back fell to the wrecking ball and no certified mail arrived from City Hall, the partners decided it was time to make a few changes.
So, in 2017, they remodeled a bit, creating a bit of cocktail lounge vibe, adding a cocktail list and building an outdoor space that’s proved popular, weather permitting.
But they managed to not dramatically change the vibe. Hence the “cocktail” and “dive bar” subtitle.
“So we decided to come in and we essentially put lipstick on the pig,” Stamates says. “All our venues could be described as cozy. That's what we go for. So we put in the booth seating, the fabric, the color, put in the overhang (above the bar). Really creating that kind of hobbit hole comfort.”
At the back of the saloon hangs a portrait of a naked woman and for years the artwork was called “The Stella.”
“We had actually picked out a different name, and I forget what the name was, but it was something very generic, like James Lovell Bar or something like that,” Stamates recalls. “None of the partners were at all excited about it. It was very blase.
“I had come in one time and I was talking to some bartenders, some staff who were hanging out and they had mentioned the picture back there. The butt was gone on that picture, because people throughout the last 40 years have been rubbing their hand on the butt and wiping the paint off.
“So I said, ‘you know what? I'm going to have my artist go ahead and reapply the butt, change the hair color, and then put ‘Stella’ on it, and we’re going to call (the bar) The Stella, because they would actually call the painting ‘the Stella.’ So I'm like, ‘let's just lean into it. We'll call it Stella’s.”
The partners all loved that, but they had one more person that had to clear the name with and that was Stella Ivory, who had been bartending at the place for more than 20 years. (Before that, she was a familiar face at Cafe Melange in the Hotel Wisconsin.)
“We wanted to make sure it was okay with her before we gave it this name,” Stamates says, “because we don't want to upset her. She wasn't exuberant. She was like, ‘okay, sure. I'm fine with it. No big deal’. She's not one to get worked up or overly excited.”
And, thus was Stella’s born.
A few years later, Ivory decided to retire without fanfare during the COVID pandemic. Stamates says he and his partners are still hoping to bring Stella back for a retirement party soon.
In the meantime, the bar is doing well, says Stamates, thanks in large part to another figure who has become a key player.
“A core piece is the general manager, Peaches (Seguin), who was the manager at Una for 17 years,” Stamates says. “When she was looking to do something different, I approached her, and it was really a nine-month sort of courtship to see if she wanted to make the move, because I was even hesitant to really try and take her on because she wasn't just leaving a bar. She was leaving a family after 17 years.
“But when she came on, her attitude, her vibrance, just her character, it really solidified the team around her, and she became sort of the face of the place. I'm just a glorified bookkeeper.”
Seguin is adept at handling a varied clientele that balances on the see-saw that is a cocktail dive bar.
“Our clientele is somewhat eclectic,” says Stamates. “We'll get the attorneys, we'll get people who work in the neighborhood. We'll get Marquette kids who are working on their Masters and their PhD, but older, because obviously you can see just from the aesthetic that we do skew a bit older, more mature than your average haunt for a 21-year-old.
“What really kind of puts us over the top with our success is all the visitors. A lot of these people come into town and they go down to the hotel bar and it’s like, ‘well, we're closing at 10’ and it can be a bit stuffy and corporate. ‘Why don't you go down to the old Jim’s Time Out?’ Those are people that we get and it's always great to meet out of towners, and this becomes sort of their launching pad to experience Milwaukee.”
Born in Brooklyn, N.Y., where he lived until he was 17, Bobby received his BA-Mass Communications from UWM in 1989 and has lived in Walker's Point, Bay View, Enderis Park, South Milwaukee and on the East Side.
He has published three non-fiction books in Italy – including one about an event in Milwaukee history, which was published in the U.S. in autumn 2010. Four more books, all about Milwaukee, have been published by The History Press.
With his most recent band, The Yell Leaders, Bobby released four LPs and had a songs featured in episodes of TV's "Party of Five" and "Dawson's Creek," and films in Japan, South America and the U.S. The Yell Leaders were named the best unsigned band in their region by VH-1 as part of its Rock Across America 1998 Tour. Most recently, the band contributed tracks to a UK vinyl/CD tribute to the Redskins and collaborated on a track with Italian novelist Enrico Remmert.
He's produced three installments of the "OMCD" series of local music compilations for OnMilwaukee.com and in 2007 produced a CD of Italian music and poetry.
In 2005, he was awarded the City of Asti's (Italy) Journalism Prize for his work focusing on that area. He has also won awards from the Milwaukee Press Club.
He has be heard on 88Nine Radio Milwaukee talking about his "Urban Spelunking" series of stories, in that station's most popular podcast.
