Mark Siffin: Times Square in Miami
Courtesy of Miami City Center
Artist's rendering of Mark Siffin's proposed City Square.

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.

"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.

Mark Siffin, in his Dilido Island home, says construction could begin in two years on City Square.
Michael McElroy
Mark Siffin, in his Dilido Island home, says construction could begin in two years on City Square.
Outdoor advertisers have given thousands to commission Chairman Marc Sarnoff, City Square's biggest backer.
File Photo
Outdoor advertisers have given thousands to commission Chairman Marc Sarnoff, City Square's biggest backer.
Artist's rendering of Mark Siffin's proposed City Square.
Courtesy of Miami City Square
Artist's rendering of Mark Siffin's proposed City Square.

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.

Warmbier said he usually ended a job with $30,000 or $40,000 in his pocket. Siffin's take: $120,000 to $160,000, he claimed.

The exchange between Warmbier and Hodge has never before been reported in detail. It's recorded in sworn documents made public in a 1978 Nevada murder case that the state's supreme court reopened in 2000.

Siffin denies Warmbier's allegations, and his lawyer, Russell Hayman, points out that no charges were filed against the developer in connection with that case. "It was my mistake to befriend him. The moment I met him, I should have never had any association with him," Siffin says of Warmbier. "But I couldn't imagine that years and years after I knew him, this subject would keep coming up."

True or false, the tale of drugs and swashbuckling oddly fits with Siffin's colorful past, which includes a globetrotting childhood with a brilliant father and a devout Catholic mom, a more-than-passing flirtation with drugs including heroin, and a long stretch of studying art and trading gems outside the United States.

He was born in 1950 in Bloomington, Indiana, to William and Catherine Fox Siffin. His father, who went by Bill, was a native Hoosier. Bill earned an undergraduate degree at Indiana University and then obtained a master's at the University of Minnesota. He eventually found a job with the Tennessee Valley Authority; then he won a fellowship to help pay his way to Harvard and married Mark's mother, Catherine.

There he earned a double PhD in political economy and government. Then the young couple moved back to Indiana, where Bill launched a groundbreaking think tank focused on aiding developing nations. Mark was their first child.

Like his son, Bill Siffin was a complex individual. He was both brilliant and mysterious, says Philip Morgan, a political science professor who spent decades working with him at IU. "Bill was generous and intimate yet still always distant," he says.

Mark Siffin's childhood was unconventional. The family frequently traveled on far-flung research trips and lived for several years in Bangkok. One long-lasting memory formed when he was 5 years old, while sitting at an outdoor café in Hong Kong. As he ate, Mark says, he noticed a pack of Chinese kids with bloated bellies picking in a sawdust pile, and he laughed: "Look at those fat kids!"

Bill Siffin grabbed his son by the arm and dragged him over to the starving children. "You're white, you're middle class, you have a good mind, and you have an obligation to conduct yourself in a manner reflective of your good fortune," he almost shouted at the boy.

The family moved to Hawaii when Mark was a teen, and he enrolled at a Catholic-run high school for military brats where he "endured a dreaded one-two punch" of nuns and Army officers, he told the Indianapolis Business Journal.

After high school, he took art courses at IU and in Philadelphia and tried to make a living as a painter. Then he moved to Paris, where he led a starving-artist lifestyle. "I had zero aspirations toward being a businessman," he says.

He spent several years in France, never finding much success. "My father sent my sister to try to convince me to stop living in $2-a-night hotel rooms, to come back to America to join the real world," he says.

Upon return, he took gemology courses, but then he left again — for Burma, where he stayed with missionaries and swapped gems.


Just more than a decade ago, Siffin proposed a project in Los Angeles much like the one he wants to build near the Arsht Center in Miami. That experience provides prescient clues about the fate of the large mall, garage, and billboards he plans to erect just off Biscayne Boulevard. First he lined up a partner — Apollo Real Estate — and then finalized a deal for a block on the Sunset Strip including the historic Playboy Building. He proposed a $250 million, 200,000-square-foot shopping center and later announced a partnership with Clear Channel to add huge LED billboards.

That, of course, alarmed residents, so Siffin launched a charm offensive. He met with condo boards, associations, and activists. The doors to a mansion he had purchased on Blue Jay Way in West Hollywood, a hilly enclave just above the Strip, were always open, he says.

Siffin cut a laid-back, philosophical figure, showing up to business meetings wearing pastel shirts and chatting easily about fine art. "He was one of the most unflappable guys I've ever met," says Steve Martin, a lawyer and former West Hollywood mayor. "Even when people started rabidly attacking him, he never showed any signs that it affected him."

One spring day, he even won over a civic activist by saving her life. Jeanne Dobrin, a gadfly and organizer who was then 81 years old, had come to Siffin's home. They talked for a while before she tried to back her car out of his driveway. "Something went wrong with my brakes, and I rolled over a curb, down a three-foot drop, and then slid all the way down a hill," Dobrin recalls. "I ended up slamming into a house."

Siffin leaped a fence, dashed down the hill, and pulled Dobrin to safety before firefighters arrived. She ended up a vocal supporter. "We have a lot of greedy developers here, but he was a very smart man, a very good man," she says.

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.

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 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. (He was never convicted of any crimes, however.) 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 Maestrales 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 his passengers were caught with cocaine-packed suitcases. He again cooperated with customs officials.

That night, Maestrales ferried Siffin and several associates from Indiana to Fort Lauderdale. In South Florida, another team of agents watched Siffin place a suitcase in a waiting car and then use binoculars to scan nearby parking lots for several minutes before ordering the car to leave. The agents apparently let the vehicle depart unmolested, and Siffin headed back to Indiana.

The same pattern was repeated multiple times over the next two months. Sometimes, Maestrales left with a "money bag" packed full of bills after flying Siffin around. By August, after filing a half-dozen reports, the feds dropped the surveillance.

Why? Warmbier offered a theory during that interview in the hospital room: Bill Siffin's government connections.

There's no evidence that Mark's father worked for the CIA, other than Warmbier and Hodge's claims in the court documents. (The agency does not respond to public requests for information about agents, even deceased ones.) But Morgan, his old colleague, says Bill Siffin certainly moved in intelligence circles thanks to his think tank. The center worked closely in international hot spots with USAID — an agency noted at the time for providing cover to spies.

Either way, on December 21, 1978, about three months after the surveillance of Mark Siffin ended, a small-time drug dealer — and the son of a local judge in Reno — named Richard Minor Jr. ended up dead after being stabbed 15 times in his living room.

Minor, Nevada police learned, was best friends with Douglas Warmbier, who police believed was in Reno the night of the murder. That's when they found surveillance records of the "suspected traffickers" Siffin and Warmbier.

Investigators noted that Siffin had started a California company called Mae Inc. They feared he was "funneling large amounts of money" through the company in order to "reinvest the funds in legitimate business areas," records show. Could the pair have whacked Minor in a drug dispute?

Agents searched for Siffin. But he had disappeared. Several weeks of attempts to find him led nowhere.

Police soon arrested another suspect, who was eventually charged with the crime and later convicted. The Siffin angle was forgotten — and never even provided to defense attorneys for the convicted man, John Mazzan. It would languish undiscovered for 20 years.

In the early '80s, Siffin re-emerged in Bloomington, where he'd married his girlfriend, Ellen, and had his first child, daughter Mae. They bought a farm stocked with corn. But he might not have shed his less savory connections.

In 1982, a federal grand jury in Illinois indicted Siffin, along with 11 others, on drug and money-laundering charges. The indictment said Siffin and the others had been using Danville, Illinois, as a distribution point in a five-state, multimillion-dollar marijuana-smuggling ring since 1976. The dealers allegedly traveled to Florida to pick up the drugs and then sold them throughout the Midwest. It was "probably the largest drug ring operating" in the region, a DEA official told Danville's Commercial-News.

The charges against Siffin were soon dropped, however.

Three years later, he was indicted again in Indiana after accusations of illegally owning firearms, his lawyer told the Herald. Again, prosecutors declined to press charges. His lawyer says authorities realized a key witness had in the past tried to extort money from Siffin.

Siffin soon gave up farming, and his marriage fell apart. After briefly flirting with derivatives trading and living a few years in Italy, he moved back to Bloomington and used his capital to found another company. Maefield Development, named for his daughter, was born in 1993. The firm started with small strip malls in the college town and then moved on to riskier ventures in Indianapolis.

"He was an eccentric character even back then," says Alec Petros, Siffin's first investor and a friend. "But you could tell he had a vision."

By 1997, Siffin had made a splash in local papers by optioning a hotly contested 41 acres in a developing suburb, rezoning it for commercial use — against a loud outcry from residents who wanted to preserve the quiet landscape — and flipping the land for $20 million.

At last, he had found his niche.


Barbara Bisno is wedged into a packed conference room inside the Arsht Center's opera house. It's this past May 6, and the gray-haired ex-federal prosecutor and former Venetian Causeway Neighborhood Association president is craning her neck to get a view of Mark Siffin. He's standing before hundreds of residents, waving his arms dramatically at a video screen like a maestro conducting a symphony. A slick artist's rendering shows digital billboards stretching 40 stories over downtown.

Bisno's jaw drops. "I had no idea this was coming," she says.

Most of the others packed into the meeting had no clue either. That is, except for the large cheering section Siffin has brought. This is his soft launch of an idea he has been cultivating for more than 15 years. And, as with his other projects, it begins and ends with money: Cold cash that bought the best lobbyists in South Florida might have also helped sway city commission Chairman Marc Sarnoff and purchased the support of condo boards and residents along Biscayne Bay.

"That shopping center is aesthetically a monster," Bisno says. "I don't know how anyone could argue otherwise."

Siffin first came to Miami in 2004, when a bank flew him to town to check out some properties. He loves the place, he says in the charmingly off-center way that has won over so many potential opponents. "I've lived in the South of France, in New Mexico, in California, and there's something extraordinary about the light here," he says. "To me, light is life. Without light, you have no colors. You can't really experience life without light."

In January 2005, he bought his Dilido Island mansion and set his sights on remaking the Magic City. First he spearheaded the face-lift at the Strand Hotel at 10th Street and Ocean Drive in South Beach. Then he joined a bid by megadeveloper Pedro Martin to buy the land from McClatchy for three new condo towers.

After the real estate bubble exploded in 2008, Martin's plans fell apart and Siffin moved to the forefront as the sole developer interested in McClatchy's land. He saw the potential for digital advertising on the site.

In 2006, he put über-lobbyist Ron Book on the payroll to persuade state officials to change billboard restrictions. Siffin then hired a mighty triumvirate to argue his case in Miami: former city Commissioner Rosario Kennedy and heavy-hitting property attorneys Jeffrey Bercow and Ben Fernandez.

Siffin hasn't given much money to political candidates, aside from a small donation to a committee backing Miami Beach Mayor Matti Herrera Bower. But outdoor advertising companies have. They are the same firms that stand to profit from the planned giant billboards. For example, Commissioner Sarnoff, who represents the neighborhood where the signs and mall are proposed, has received nearly $5,000 from donors listed explicitly as "outdoor advertising" interests, including execs from Van Wagner Aerial Media and Worldwide Rush.

In Miami, Siffin has orchestrated the same hearts-and-minds campaign he set up in West Hollywood. Neighborhood leaders and condo boards were invited to his home. "Mark is one of the most creative guys I've ever met," says Murray Dubbin, a retired Miami Beach city attorney who now heads the condo board at the 801 N. Venetian Dr. building. "He's extremely bright and seems detail-oriented. You feel he's going to get done what he says he'll do."

But Siffin has also shown his mastery of talking without saying much. "You sit with Siffin, and he's smooth and smart and engaging," says Parker Thomson, a veteran lawyer and member of the Arsht Center board of directors who says he still has not made up his mind about the project. "But when you're finished, you shake your head and say, 'What in the world did I just hear?'"

That goes double for Siffin's grand Arsht Center speech in May. The garage? "Automotive storage" in Siffin-speak. The billboards? "Media towers." Their purpose? "Entertainment" and "information."

Bisno and others left baffled. Then their fears were confirmed. On June 30, just a month after the meeting, the Omni Community Redevelopment Association (CRA) issued an expert report on the impact of Siffin's signs. It was blunt: They would blast the equivalent of "four full moons" on nearby residences, according to Main Street Engineering's analysis. "It is [also] important to note that the signs will be emitting a constant color-changing scheme which will result in additional offensive glare," the engineers wrote.

Here's the strangest part: Just two weeks after the damaging report came out, the longtime head of the Omni CRA, Jim Villacorta, was fired. His replacement: a Sarnoff subordinate named Pieter Bockweg, who has spent the past two years crafting a new sign code for the city.

Again, the echoes of West Hollywood were unmistakable. To one of the largest condo associations nearby, Plaza Venetia, Siffin gifted $300,000. To the city, he pledged $2.2 million in annual "fees" and a "voluntary" $800,000 yearly toward the city's Museum Park project.

On July 22, the city commission voted 5-0 for Siffin's plan. Just seven days later — after fudging the requirement to advertise a second vote in two weeks — the commission took up the plan again. During a limited public comment section, the only real opposition came from a former Herald reporter and Miami-Dade County lobbyist named Eston "Dusty" Melton. He pointed to ordinances in the city code, the county code, and federal legislation that all seem to bar Siffin's signs.

"The history of this commission is to empower and approve behavior by sign companies and developers... who brandish city approval that runs counter to the law in exchange for giant wads of cash," Melton said from the podium. "Some of us fear that's what we're seeing here again today."

The commission voted 4-1 to finalize the deal. Frank Carollo was the only dissenting vote. "What is the rush?" he asked.


"Hang on!" Mark Siffin says with a crooked grin and momentarily leaves the room.

It's a humid summer afternoon at his Dilido Island home, and the bay windows are cracked open as usual. Workers hum around, refinishing woodwork and trimming hedges. Donalee, smiling, comes in and offers iced tea.

Almost a month has passed since the commission gave Siffin the go-ahead to proceed with City Square.

He returns with a glossy coffee-table volume of impressionist art and opens to a page of pastel Monets.

"This book is all about the initial reactions of Parisians to the impressionists. They were like, 'Oh, my God, it's so garish!'" Siffin says, leafing through the artwork. "Some of the words I've read about my media towers are so similar to what Parisians said about what is now considered some of the finest art in the world."

He suddenly looks worried about the comparison. "My only real point in that regard is that shifts in societal forms of expression often generate an upheaval, like this thing," he says, hoisting his BlackBerry. "It is who we are, and it defines how we interact... These towers will have built-in text features that will allow you to interact with them and receive apps from them."

This is how Siffin talks about his project — in terms of "societal shifts" and classical painters, not the millions of dollars he stands to make.

The project still faces hurdles. Melton is right that county, state, and federal codes prohibit the signs. And Siffin is already being sued. Cooper Carry, an Atlanta architecture firm, put liens on the property last November, claiming Siffin and McClatchy stiffed it out of $400,000 for designing City Square's initial plans.

But Siffin's lawyers are working county commissioners and state regulators. Bercow, his Miami attorney, says the project is on track to begin construction in less than two years.

Plus there's a key difference between City Square and the disastrous effort in West Hollywood: No real opposition has materialized in Miami.

Bisno, the former federal prosecutor, believes Siffin violated the city's rules by ramming City Square through the commission so quickly and with so little public input. Former Mayor Manny Diaz helped pass the Miami 21 plan largely to prevent such fast changes. "There's a very well-defined process the community has become familiar with: public hearings, review by the planning department, and the urban review board," Bisno says. "He ignored all that."

But she concedes that her neighbors haven't mobilized, in part because Siffin cannily finalized the plan over the summer, when a huge number of snowbirds were far from Miami. "A lot of those people have still heard nothing about this whole deal," she says.

As for Siffin, City Square seems the closest he has ever come to fusing his many complex instincts: to create lasting urban change, to contribute to society's evolution, to make a boatload of money.

As obtuse as this onetime gem trader, oft-accused drug dealer, oil painter, millionaire, and son of a brilliant academic can be, he also sounds deadly sincere: "When I'm no longer here, the key thing is that whatever I did continues to reverberate," he says, chewing on his diction, his eyes squeezed shut. "My only job is to do whatever I do as well as I can."

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