Mark Siffin: Times Square in Miami

Mark Siffin stares dolefully at the canvas. He just can't get it right. The seven-by-ten-foot painting leans against a wall inside his $2.6 million waterfront Dilido Island mansion. In the image, a naked, large-breasted, drop-dead beautiful blonde cracks a slight smile while leaning back provocatively. She's rendered in flamingo pinks and Florida-sunset oranges, contrasted by cool azure flowers.

Michael McElroy

Mark Siffin, in his Dilido Island home, says construction could begin in two years on City Square.

File Photo

Outdoor advertisers have given thousands to commission Chairman Marc Sarnoff, City Square's biggest backer.

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"I was up at 3:30 in the morning working on this," says Siffin, who has cropped gray hair, intense gray eyes, and wears a striped green shirt with a tightly knotted tie. "It's been driving me nuts."

Just then, his wife, Donalee — a former television reporter in Portland and Los Angeles — strolls into the spacious living room. With her long hair, sculpted body, and bright smile, she's no doubt the subject of the painting.

Siffin isn't embarrassed. He's a man who has it all, and he's poised to have much more. In just the past year, he has seemingly come from nowhere to control the future of downtown Miami.

In the next month or so, he'll ink a staggering $190 million deal with McClatchy, the Miami Herald's parent company, to buy a ten-acre plot of land opposite the Adrienne Arsht Center for the Performing Arts. His plan: Build a boutique shopping center and garage topped with two gargantuan, 40-story digital billboards that will forever change the Magic City's skyline.

In Siffin's view, City Square is the final turn of the "Rubik's cube" of a revitalized downtown ­— a place for people to park, to party, and to hang out after concerts and plays. "It delivers a critical piece of the urban landscape," he says. "It creates life in an area around the arts center."

But the oil painter's neon-colored vision has drawn a loud chorus of criticism, especially because the city commission seems to have skirted the law in order to approve it this past July 29. There was only a week of review and virtually no public input. Some detractors fear the signs' Times Square tackiness will ruin neighborhoods along Biscayne Bay. Others say the billboards are illegal. And then there are the questions about Siffin's character.

Among the findings of New Times' investigation of Siffin: He's been convicted of heroin possession with intent to sell; a drug dealer claimed Siffin pulled in six figures in marijuana shipments; and the developer has been tied to a South Florida pilot who ferried millions of dollars' worth of drugs. What's more, he promised to develop neighborhoods in Los Angeles and San Francisco but left behind a vacant, blighted lot and a historic building riddled with problems. In Miami, Siffin paid hundreds of thousands of dollars in hush money to condo boards and lobbyists in order to engineer the backroom deal for his mammoth project.

There's no question Siffin is brilliant, alluringly eccentric, and unusually open. In Miami's long and wild history of developer-barons — from Henry Flagler to Tibor Hollo — there's never been anyone quite like him. But while city leaders have welcomed and praised his project, the questions raised by his past are troubling.

"Everyone should worry that somebody like Mark has total control over something with such a major impact on this city," says Barbara Bisno, a former assistant U.S. attorney and opponent of the project. "He's ultimately going to develop a project that benefits Mark Siffin, not Miami."

Doug Warmbier, a construction worker with a history of drug convictions, lay in a hospital bed, mostly paralyzed below his neck. A month earlier, he'd swerved to miss a deer on a highway outside Indianapolis and rocketed off the pavement. His dog, perched next to him, died instantly. Doctors expected Warmbier to walk again but told him it would take time and rehab.

Just before noon April 26, 1997, a criminal investigator from Nevada named Michael Hodge showed up in Warmbier's room. He seemed like a nice guy and talked about his own son, a quadriplegic. Then he began asking about Mark Siffin.

"Siffin," Warmbier's eyes narrowed as he talked about his old friend from Bloomington, Indiana. His eyes teared up. "He's fucking scum," Warmbier said. "I will do whatever it takes to burn him."

Had Siffin ever been caught moving drugs? Hodge wanted to know.

"One time in Morocco," Warmbier told him. "His dad got him out of trouble." Everyone knew, Warmbier added, that Siffin's father was a high-ranking CIA official. Hodge nodded and scribbled in his notebook. He'd heard that too.

Hodge asked if Mark could've killed a man.

Warmbier answered, "It would not be beneath Mark to have killed." But, he added hastily, he didn't think Mark actually had knocked off anyone.

They talked for a few hours, Warmbier in his bed, Hodge sitting in a stiff chair while taking notes. Warmbier, who spent two years in prison on a cocaine-dealing conviction in the early '80s, described their operation: He had worked under Siffin in a gang, he said, "nothing like the Colombians, but it made a lot of money for its size." The organization moved drugs — mostly pot and Thai stick — around the United States, including Hawaii.