Jimmy Fitzgerald sits outside the Flat Iron Building in Wicker Park, his hand-painted cane in one hand and a crucifix in the other, and surveys the passing scene. He’s a familiar presence at the southeast corner of North and Milwaukee, where he sets up his folding chair twice a day, six days a week, in the early morning hours and again from noon to one. Sundays are reserved for rest and mass, but Monday through Saturday, no matter the weather, Fitzgerald can be found in the same spot, manning his front-row seat at the neighborhood’s eclectic street parade. “It’s like a hobby,” he explains in his slow, rumbling voice.

Most people ignore Fitzgerald–he is, after all, somewhat odd-looking. On this bright September afternoon he wears a trench coat over old, mismatched clothes, a fire officer’s hat, and untied red tennis shoes. His huge round belly protrudes over the edge of his waistband, and his boyish face–he’s 56–is offset by a big double chin and a lazy eye. Some passersby say hello–he mumbles a greeting–and a few mostly local old-timers stop to chat. “People tease me,” he says. “They call me the Mayor of Milwaukee, North, and Damen. The garbagemen say, ‘When are we gonna get our raises this year?’ I say, ‘I’m trying.'” He roars with laughter.

But it’s not garbage trucks Fitzgerald watches for on his daily vigils–it’s roofing trucks. Fitzgerald’s been captivated by roofers since he was 17. “I just seen them working on a building where I used to live with my parents on Milwaukee,” he says. “I just got fascinated by how they were working. Ever since then, I’ve been interested in roofing.”

When he spots the trucks rolling through the intersection he takes a notepad out of his shirt pocket and carefully writes down the company name. He’s done it twice already today. He can’t read or write very well, and calls himself “handicapped.” “But I can copy what I see–that’s the only way I know how to write,” he explains. “I copy the name on the truck, and that’s what I write down.”

Then he goes up to his room and draws their pictures. In the six years he’s lived in the Flat Iron Building he says he’s amassed 2,099 drawings of home repair and roofing trucks and thrown out perhaps thousands more. The ones he’s kept are numbered and dated. “It’s my private collection,” he says. “I do it for my own pleasure. They’re not for sale.”

While Fitzgerald’s truck drawings are off-limits, he’s quite willing to part with his other, more “commercial” works–bright acrylic paintings of subjects ranging from nature (flowers, fish) to city life (high-rises along the lake, Saint Mary of the Angels Church). During the recent Around the Coyote arts festival, Fitzgerald sold eight paintings, pocketing enough cash to cover over half of his $350 rent.

“Jimmy sells more artwork than anybody in the building,” says Roberto Lopez, the longtime Flat Iron denizen and gallery owner who took Fitzgerald under his wing in 1995. “He’s, what do you call it, a naive artist, painting things he likes in his own style. He’s the kind of person that can see angels. His mind is like the state of a child’s. There’s a lot of innocence in Jimmy.”

Even when he’s not sitting outside, the Mayor’s not hard to find. He rarely strays from the building’s confines unless he’s shopping at the Aldi up the street, off on an “outing” with his caseworker, or seeing his doctor–he has heart and blood pressure problems. He’s heavy, and it’s hard for him to get around. Though he frequently complains of not feeling well, his third-floor room (or “artsudio,” as it says on a signboard just inside the building’s entrance) is usually open to visitors. He’s a bad speller by his own admission, and a sign on his door says: “James Fitzgerald, Arters.”

About two dozen of Fitzgerald’s paintings hang in the hallway outside his room, many of them with titles or short descriptions painted right in. There are patriotic scenes (Neil Armstrong on the moon, the Blue “Angles”) and movie stars (Chuck Connors, W.C. “Fells”). There’s also a big picture of John Dillinger robbing an Oklahoma bank–in 1936, two years after the outlaw was shot down. The pieces cost from $10 to $45; some have sale prices like $10.65, $26.55, and $35.75. They’re all signed “JF.”

How does Fitzgerald decide what to paint? “I lay down in the afternoon and take a nap and it just comes to me,” he says. “Then I get up and start drawing it, whenever I have the inspiration for an idea.” It takes him about two days to make a painting; Lopez and other friends help set the prices, which are written on scraps of paper taped to the wall next to the paintings. Fitzgerald’s not worried about anybody stealing them. “Nobody touches them,” he says.

Fitzgerald is a big country and western music fan, and his closet-sized room is a shrine to Nashville. Covering the wall behind his bed are more than 100 pictures of country music stars that he’s cut out of magazines and newspapers, many of them framed, plus several handwritten lists of “all the names of every legendary country and western singer that ever lived,” as Fitzgerald says. He also has lots of albums and tapes. He took to country music at an early age–he can recall his parents listening to the Grand Ole Opry and the WLS National Barn Dance in the late 1940s, when he was just a kid.

“All of a sudden I heard this sound coming from the radio,” he says, and starts yodeling. “I was jumping up and down on my mattress having a good time–it was a happy kind of music. I asked my mama, I said, ‘Mama, mama, mama, what’s that music, that sound? What is that, mommy?’

She said, ‘That’s country western, that’s Jimmie Rodgers, the Mississippi yodeler.’ The second one I heard was Patti Page, ‘Mockingbird Hill.’…I was just jumping up and down, bouncing up and down on the bed to this happy music.”

Fitzgerald, an only child, was born in 1945 and grew up on the northwest side, near Dawson and Kimball. His father, Joseph, was a machinist; his mother, Alma, had a hard time getting around due to a hip condition. The family moved to Wicker Park sometime in the 1950s; Fitzgerald attended Burr Elementary, where by his own account he was deemed slow. “Art was my favorite subject,” he says. “I thought that was the easiest thing to do. Subtracting, adding, figuring, counting–forget it. I don’t know nothing about that, too hard. The easiest thing to do was draw pictures.” Fitzgerald says he was 17 by the time he reached eighth grade. He neither went to high school nor received any kind of special education.

The family lived in an apartment at Milwaukee and Wabansia, and later above a pizza parlor at Damen and Wabansia. In 1972 Fitzgerald’s father suffered a fatal heart attack in front of a hot dog stand on Damen; his mother died a month later. His uncle Herbert, a janitor, took over caring for him, and the two eventually moved into a four-flat at North and Wolcott. But Herbert died of Alzheimer’s in the mid-1980s. Fitzgerald continued living

in the building for another decade, watched over by friends, relatives, and caregivers.

Fitzgerald has never had a job. “I just never knew how to do anything,” he says. “I’m overweight and have health problems and couldn’t work.” He got by on disability checks and his father’s pension. When the building on Wolcott was sold in 1995 and the new owner promptly evicted him, he panicked. He turned to Lopez, whom he’d befriended in about 1985.

“Jimmy came to me and said he’d been kicked out,” recalls Lopez. “He was all freaked-out. He needed a place. I was working for the building then, and I thought, why not help this guy?” At the time, Lopez occupied a large partitioned space on the third floor, which he also used as an exhibition space for his photographs and other artists’ work. He settled Fitzgerald into the smaller room, charging him $300 a month. In the hasty move, Fitzgerald had to get rid of many of his possessions, including his family photographs and the many truck drawings he’d already done. “I wasn’t sure how big of a space I was gonna have. I left a lot of things I wished I would’ve took with me.”

At first, Lopez says, he tried to keep Fitzgerald out of sight, fearing the building’s managers would think he was a squatter and throw him out. “He couldn’t live in this place, because this is a building for artists.” But he knew about Fitzgerald’s artistic leanings, so he hatched a plan. “I taught him to paint,” says Lopez. “I spent three, four months talking to him about the meaning of art. I used to steal supplies from artists and give them to Jimmy–I did it because he was somebody in need. I was pushing and pushing him. I would look at his artwork and criticize it….As a nobody, he could get thrown out of the building. But as an artist, he could be somebody here.”

“Roberto helped me,” recalls Fitzgerald. “He gave me old canvases and paints to practice. He said, ‘Can you draw a little picture of something, some flowers or some other thing to prove you’re an artist? See what you can do, try your best.’ After he’d seen a few pictures, he said, ‘Not too bad.'”

Flat Iron owner Bob Berger and manager John Zimmers found out about Fitz-gerald after paint-ings began appearing in the hallway and his name and newfound occupation went up on the door. According to Lopez, Zimmers wasn’t too pleased, but he softened when Fitzgerald started pay-ing rent to the realty firm instead of to Lopez. Still, Fitzgerald wondered if he’d be able to stay in the building.

One day he got a knock on the door. “There was a tall, bald-headed man with a little beard,” he says. “He said, ‘Hi, how are you? You’re Jimmy Fitzgerald?’ I said yes. ‘I’m the owner, Bob Berger. Pleasure to meet you. I hear you’re an artist. You paint pictures, huh?’ It made me so happy when he had that smiling face. I felt so calm–I was worried. I said, ‘Can I hang my pictures all over the wall?’ He said, ‘Put ’em anywhere you want.'”

Lopez was let go as the Flat Iron caretaker a few years ago, but he stayed in the building, moving into another third-floor space. Fitzgerald stayed in his old room. “He’s part of the neighborhood and we’re glad we could give him a home,” says Berger. “He’s a damn good artist–he has a good sense of color. We liken him to our Henry Darger, our Bill Traylor. And he’s as nice a man as you could know.”

“I don’t like the way they do roofing these days,” says Fitzgerald. “They don’t do it the old-fashioned way. The old way, you always knew when there was a roofer in the neighborhood, that smell of tar. I’d just track it like a dog, follow where the odor’s coming from, the way the wind is blowing. I just followed it till it got stronger and stronger, till I listened for the sound.

“But the last couple years, it ain’t that way no more. The old-timer people all left that used to have it done that way. Now all these new condos and new buildings, they have a supply company put all this stuff up on the roof. You can’t talk to them because there’s nobody to talk to on the ground. They’re all up on the roof. You can’t see or smell anything. You don’t know where they’re working, unless you happen to be walking down the street and you see it in the alley…. I used to have friends in the business, but no more.”

But that hasn’t stopped him from dreaming. There are several toy trucks in his room, including one he’s modified: hooked to the back is a tar-kettle trailer that Fitzgerald built using an old transformer box, pipes, and metal scraps. On the side of the truck he lettered: “Stormshield Roofing Comy. Gutters. Tuckpoing. Siding. Remodling. Free Estimes. Elc Work.”

“I made that name up,” he says. “‘When we fix your roof, you’ll be shielded from the storm’–Stormshield. I even had a nightmare or a dream about it one time. I won the million-dollar lottery. I went into business for myself–I had my own roofing company. I bought a couple of trucks, equipment, and everything. I was sitting like a big shot with my feet up on the desk in my office. My name is on the chair. It said ‘J. Fitzgerald, Stormshield Roofing Company. James Fitzgerald, Owner.'”

He says he keeps his truck drawings in binders, in a cabinet. “I can’t do them forever–I might do it for one more year. Then I’ll have a memory of what I used to do…. When I get too old and I can’t go very far or do anything anymore–when I’m 75, 80 and I can’t do it no more–I’ll look at them and say, ‘I remember when I’d seen this roofer in the neighborhood, in so-and-so month and year…'”

Does he ever let people look at them?

“If they want to, I guess. I don’t know if anybody would ever be interested.”

I tell him I would. Could I see one?

Fitzgerald hands me his notepad, but there are no drawings in it, just the names of companies he’s written down.

But could I see a drawing?

He hesitates. “No, not now.”