In art dealer David Leonardis’s eyes, the difference between New York and Chicago is that you get to take your asking price and “add a zero.” So in January, after ten years in business, Leonardis decided to close his Wicker Park space and head east. In February he put a Going Out of Business sign in his window and had a clearance sale–100 pieces priced at $100. Then he made sales 30 days in a row, and a new sign went up: “Staying in Business! Thanks for your support Chicago. Come on in and buy some art!”

Leonardis opened his namesake gallery in April 1992, after a year and a half selling various articles out of his apartment and from a booth on Belmont near Racine. The gallery was originally at 1352 N. Paulina, but in July 2000 he bought the two-story building at 1346 N. Paulina and moved it to the first floor and his residence to the second. That year turned out to be his best ever for sales, but it closed on a sour note with his worst-ever November and December–traditionally his most profitable time. He points the finger at the Bush-Gore election debacle. “If you think people are worried about spending their money during times of war, forget about it when they don’t know who’s going to be in control of the country.”

Then came September 11. He saw the event with two sets of eyes. “I started freaking out is what I started doing. Because, believe me, that wasn’t good for the art business. It’s certainly not good for all the people that died.” After the attacks he headed to New York, where he’d been visiting for years. “I just felt safer there, and I really wanted to be a part of what was going on. So I rented out my apartment and moved.”

Back in Chicago there was talk that he was looking to unload his building. “He had told me in September that he was interested in selling it and that he didn’t know how much longer he was going to be around,” says Olga Stefan, executive director of Around the Coyote. Then last November Leonardis got a six-month “foot-in-the-door deal” on a gallery space in New York.

Leonardis has featured quite a few Chicago artists in his time, but he also scouts for talent elsewhere. A good portion of the work he shows tends to be of the outsider and self-taught variety–paintings of superheroes, colored-pencil sketches of pictures in magazines–and starts at the $100 mark. But ever the salesman, Leonardis says if “you bring the big checkbook we have a few $10,000 items for you.” One artist he peddles hard is the late Reverend Howard Finster. Leonardis first approached Finster more than a decade ago. “I told him I was a fan and that I wanted to make T-shirts. We agreed on an image, and then when I made my first run he traded me art for T-shirts. He told me that if anyone got saved because of one of my T-shirts, I would get extra-credit points in heaven.”

Besides the T-shirts, Leonardis sold a lot of signed prints of Finster’s work over the years. “At one point Finster was getting a little too old to sign them,” says painter Kristen Thiele, who was making the prints for Leonardis. “So we stopped.” Leonardis was visiting the ailing artist down in Georgia on the day he died last October. “He told me, ‘Well, I’m not feeling so good,'” says Leonardis. “‘But you go get some food out of the icebox.’ He was always just such a nice–I mean, I had a relationship with Howard for 11 years. He made me, as they say. I published his work and I sold his work and his job was to save your soul and my job was to sell you valuable contemporary folk art.”

Leonardis’s New York gallery lease ended a few weeks ago, and he moved his pieces to a storage locker. He’s looking at new venues, but “every one of them takes money.” He’s keeping his apartment there, having recruited two of his artists to run the Chicago gallery while he commutes back and forth.

One of the reasons he likes New York is the big names. In the bathroom of his Chicago gallery hangs a photo of him with Bill Clinton. He’s recently met Joe Frazier and Ron Silver and shaken hands with Queen Noor of Jordan. “She was the most elegant woman you could imagine. However, I didn’t have the nerve to ask her for a photo. Next time for sure.” What’s missing in Chicago, he says, is the energy and excitement that a star’s presence can bestow. “Them shutting down the ‘Inc.’ column in the Tribune–that’s bullshit. That’s why people are leaving the Chicago art scene. People love the hype, so let’s give it to them.”

Thiele, who recently moved to Florida but still sells her paintings through Leonardis, was worried when he told her he was going to close up shop in Chicago. “I thought there was a possibility that he would end up with nothing. Because he would alienate everyone in Chicago by leaving and he would maybe not make it in New York. So I wasn’t sure. And I still think he’s kind of unsure himself. Because I don’t know if circumstances have jelled there in New York.”

Indeed, despite the “incredible show of support” he received in February, Leonardis sounds slightly ambivalent about his space here. “It’s like I put up my ‘Yeah-I’m-staying-in-business-sale’ sign, and I am staying in business. But we’ll see how it goes.”

On the other hand, “I’ve sold a lot of art in Chicago. I’m continuing to sell art in Chicago. I think that my little [going out of business] sign really kicked people in the ass a little bit and made them realize: you know, you’ve got to buy art.”

Art accompanying story in printed newspaper (not available in this archive): photos/Nathan Mandell.