For the ninth straight year, October is Dining Month on OnMilwaukee, presented by the restaurants of Potawatomi Hotel & Casino. All month, we're stuffed with restaurant reviews, dining guides, delectable features, chef profiles and unique articles on everything food, as well as voting for your "Best of Dining 2015."

The dining scene is tough and sometimes even smart owners with a strong concept can’t make a restaurant work. However, some spaces seem more challenging than others and change hands more frequently.

Here are 10 of these tricky spots – a few of which finally found the right tenant.

2321 N. Murray Ave.

The Winchester opened in this locale in September 2014, after former tenant, Two Bucks, suddenly shuttered earlier in the year. Prior, this spot was briefly home to The Dog’s Bollocks and before that, the French eatery Elliott’s Bistro. This high-traffic space is within walking distance of theaters, bars, cafes, music venues and other restaurants, but it often struggles to find its niche. The space is also large and can sometimes feel cold. The Winchester, however, is off to a strong start and will hopefully revitalize the spot.

1815 E. Kenilworth Pl.

In the past decade, Cans Bar & Cantina and Southport Bar & Grill have occupied the space that is currently School Yard Bar & Grill. Anyone remember when it was a Rocky Rococo’s in the 1980s?

221 N. Water St.

Lucky Ginger seems to be off to a good start, but Cynthia’s Restaurant wasn't the right fit for this space which was formerly Soup’s On and, before that, Pier 221.

770 N. Jefferson St.

Neither Señor Frogs nor Howl at the Moon could make this space work. It was also home to Fresche Pizza, Sun Toy’s and more. Breaking up this large, lower-level space and focusing on the lunchtime crowd was a good idea – Chic Cafe and Shah Jee's are popular with Downtown workers and loungers.

728 E. Brady St.

Casablanca is clearly here to stay. A few years ago, the Middle Eastern bar, restaurant and hookah lounge underwent a massive renovation that included the addition of an opulent second story. However, this spot was tricky for other businesses that didn’t make it, like Club 728, Rudy Valentino’s, DiSalvo and Brennan’s, and Tarantino’s By the Sea.

500 N. Water St.

Joey Buona’s has been in this space for almost a decade, but before the Italian eatery moved in it was Brett Favre’s Steak House, Nitro, Park Avenue and The Madhatter. The building is set to be converted into a hotel. 

202 W. Wisconsin Ave.

Kiku Japanese Restaurant had made this location work for the past six years, but the owner filed bankruptcy last week. Before Kiku moved in, the corner space was vacant for a few years after Aladdin closed, preceded by Salad Maker and Charhouse Grill and Taco Bell.

1014 N. Farwell Ave.

After housing restaurants for decades, including La Casita, Sol Fire, Pepe’s Rockin’ Tacos and The Eatery On Farwell, this locale is now home to a flower shop, Belle Fiori. It’s too bad the high-profile patio isn’t available for dining anymore, but maybe buds are a better biz for this formerly unstable site.

1100 S. 1st St.



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Before the thriving Circa 1880 moved into this space, it was Marchese’s Olive Pit, Lava Java and 1100 Club.

2213 N. King Dr.

In the early 2000s, Karl Kopp owned this building and allegedly had plans to open an upscale lounge, which never happened. In 2006, Soche opened after a $1 million renovation project, but closed in early 2010. It reopened, briefly, as Paje in 2012, which also closed. It opened as SkyBox Sports Bar last year.