Alas, not all of his critics required dramatic rescue, so Siffin turned to his pocketbook. He wooed residents of a condo on Alta Loma Road with a $200,000 cash gift. To another association, he promised $120,000 for a new roof. In exchange, they signed a pledge not to criticize his plans "in the news media." And he offered a $5.2 million "fee" and a share of billboard revenue to the city.

When activists realized what was going on, they sued to block the deal. But in early September 2001, the council approved his Sunset Strip plans by a 3-2 vote. The swing ballot was cast by an 81-year-old former Army combat medic named Sal Guarriello, who had at first voiced skepticism. But the day of the vote, Guarriello voted yes without discussion. Why the change of heart?

The L.A. Times offered one possibility: Siffin had quietly donated $21,000 toward Guarriello's dream project, a veterans' memorial in Hollywood, the same day as an initial vote a month earlier.

Mark Siffin plans to top City Square with twin 40-story digital billboards.
Photo courtesy of
Mark Siffin plans to top City Square with twin 40-story digital billboards.
Photo courtesy of

Siffin maintains he did nothing wrong. "These residents deserved to be compensated for the trouble the project would cause them," he says of his payments to condos. "These were not payoffs." As for Guarriello's donation, he chalks up the controversy to bad timing.

But many in Hollywood were outraged, including former supporters such as Martin, the mayor. "It was ridiculous, the timing of that donation," he says. "It brushed anyone who supported the project with a patina of corruption. It was totally unfair, and it made me look like a fucking idiot."

On January 24, 2002, the West Hollywood Council flipped its previous vote and rescinded approval for Siffin's billboards. Four weeks later, his partner, Apollo, kicked him off the project.

It was a devastating turnaround. But Siffin says he has no regrets. "I wish I could have completed the project, but I was very proud of what we accomplished."

So he returned to work, moving ahead with plans to rehabilitate a century-old, seven-story gem in San Francisco's Union Square neighborhood. "It was completely collapsing, and everyone said, 'Oh no, don't go in there, the preservationists will eat you alive,' " Siffin recalls. His firm bought the building out of foreclosure in 2002 and, two years later, sold out its 39 condos at prices ranging from $300,000 to $1 million.

"Now, " he says proudly, "this place is on the cover of a book about successful restorations."

But he doesn't mention he is embroiled in a lawsuit with the building's condo association, which claimed in 2007 that he did a sloppy job. Roofs and walls are crumbling, windows leak, and decks have deteriorated, the plaintiffs claim. The total damage: more than $1 million. That suit is ongoing.

A third, more recent project has also run into roadblocks and controversy. In 2008, Siffin announced plans to turn a lot in L.A.'s blighted Panorama City neighborhood into a 452,000-square-foot mall and a 500-condo development. Also included: huge LED signs on the walls. The package would cost $200 million.

Unlike in West Hollywood, most people in the area supported the idea. "This is a lower-income area, and any big development that would improve lighting is welcome," says Tony Wilkinson, president of the neighborhood advisory group.

The problem: After community meetings were held and a flashy mockup was presented, the project seems to have quietly died. The intersection remains a fenced-off, trash-strewn lot.

Siffin says he still intends to build there, but the recession leveled his plans. "It's part of an area that has experienced incredible difficulties," he says.

Wilkinson has a different take: "He's an unusual guy, but he's a typical developer in one sense: He talks a good game even when he doesn't have the money to pull it off. He seems to be one of these guys who specializes in getting the government to approve a project but not in actually ever getting anything built."

In his 20s, Siffin returned to Indiana and fell in with a rough crowd. He was convicted in New Jersey in 1973 of heroin possession with intent to sell. More detailed records are not available, so it's unclear what precisely happened. He was sentenced to probation. Hayman, his lawyer, told the Miami Herald that the drugs were for "personal use." Siffin declines to discuss in detail his brushes with the law.

Court records show DEA agents tailed the 27-year-old Siffin a few years later, in July 1978. On one typical night, a special agent and two cops tracked him to the Bloomington airport, where Siffin pulled a dark BMW into a private hangar at 6:15, hopped out with a suitcase, and boarded a waiting plane.

The pilot, Gus Maestrales, would eventually carve out his own bizarre history in South Florida. In 1980, two pilots working for Maestrales were caught flying suitcases full of cocaine. Records show that DEA agents believed Maestrales was a "narcotics transporter." In 1985, federal customs agents nabbed the pilot flying two men with almost $6 million in cash bound for El Salvador and accused the trio of smuggling. Charges against the Fort Lauderdale-based pilot were later dropped when the other men pleaded guilty. A couple of years later, two of Maestrales' passengers were caught with cocaine-packed suitcases. He again cooperated with customs officials.

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