Jerry Kleiner’s highs and lows

Can the restaurateur bounce back after so many closings and lawsuits?

Jerry Kleiner

Jerry Kleiner Illustration: Kira Shaimanova

When I meet Jerry Kleiner at Carnivale, the Nuevo Latino restaurant he opened in 2005 in the West Loop, I find him alone at a table busily sketching new lampshades to replace the giant hot-pink fixtures hanging in the bar area. “They’ll be a little bit bigger,” he says, straining to be heard above the boisterous lunchtime crowd gabbing over a salsa soundtrack. “They’ll have multicolored stripes and a rosette on the bottom.”

More impact. More color. A near OCD-level attention to detail. It’s a mantra the restaurateur liberally applies to his restaurant designs—and to his person. Dressed in a bold purple Izod tucked into blindingly white shorts cinched with a gleaming white patent-leather belt and a pair of white leather sneakers that have never seen a scuff, Kleiner appears at least a decade younger than his 55 years. After nearly 30 roller-coaster years in the restaurant and nightclub business, that’s saying something.

From the late ’90s to the mid-2000s, Kleiner was on top of Chicago’s entertainment world, at one point co-owning eight restaurants and nightclubs, and lending his signature more-is-more design to all of them. Each opening seemed bigger, brasher and more riotously colorful than the one before, and each location, from Randolph Street to the South Loop, blazed a trail other restaurateurs raced to follow. But the tail end of the aughties were not so kind to Kleiner. As the faltering economy ransacked his revenues (and that of plenty of other restaurateurs), his once-hot spots started shuttering. Red Light, Marché and Opera all closed in the nine months between June 2010 and March of this year. In May, 33 Club closed. Kleiner, a designer and restaurateur once so prolific in his ribbon-cutting that he was becoming the Starbucks of Chicago’s restaurant and nightlife scenes, hasn’t opened anything since 2009.

The economy’s disastrous effects on Kleiner’s empire also played out in the Cook County Circuit Court. Since 2009, Kleiner has been named in 11 lawsuits. Vendors such as produce suppliers complain of bills unpaid, a management company alleges rent payments long overdue for Marché and his former company’s offices, and a bank is suing for a nearly $400,000 loan in default. The biggest lawsuit yet, however, came just one month ago. Anthony Tomaska, a former partner at 33 Club, alleges Kleiner and another partner, Sam Madonia, committed fraud when they entered into an agreement to put up cash for the restaurant, and siphoned away investor money for Kleiner’s personal use. Tomaska is asking for $1.8 million from Kleiner and $1.1 million from Madonia.

How did Kleiner get into this mess? Critics and friends I spoke to, all of whom say he’s as charming as he is talented, offer varying theories: His artistic temperament isn’t suited for making sound business decisions; he’s picked questionable business partners and entrusted them with his restaurants’ finances; he’s a slick character who thinks he can get away with not paying his debts. But the bigger question is: With his reputation so tarnished, can Kleiner claw his way back to the top?

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