On one trip out, around 3 a.m., he noticed that the flood had dislodged the stakes holding the plane, and it had begun to shimmy. So Tiller stood on his tiptoes and draped his 160-pound, five-foot-seven body over the end of the left wing, offering himself as a human paperweight to the mercy of the sky.
The horizontal torrent drilled into the back of his skull, splattering his light brown hair into his face. He spread a towel over his head. The rain still felt like razor blades. Eventually, fortuitously, his waders filled with water. Even as his toes were shriveling into jaundiced prunes, the ballast in his trousers held the plane in place. Four-and-a-half hours he half-stood, half-hung, muttering to himself, "God, I don't know what the hell I done to deserve this, but if you stop that raining, I'd sure appreciate it."
The weather slowed enough that Tiller could let go a couple of hours after sunup. He staggered to his friend Howard Lamb's house, where he crashed spread-eagle on the wet floor. Then they heard the wind come up again; the metal porch popped off the front of the house and flew across the street. By the time the storm abated, pinched nerves piped pain to Tiller's neck and right shoulder.
Weeks later, still relying on Motrin for mobility, he tramped from the plane across the grass to a neighbor's trailer near his plane. The home's sides were dented, broken, peeled, and agape. It looked like it had been kicked up a concrete staircase. "I tell you, that was the scaredest I've ever been in my life," Tiller said in describing that night. "And I've been in some scary stuff."
Battered, broken, living in obscurity, this quasi-hermit was once a linchpin in the fortunes of one of Florida's biggest businesses: the Seminole Indians' gambling operations. From 1982 to 1996 or so, he was close enough to then-tribal Chairman James Billie to secure some small deals with the tribe -- selling a few discount Chinese Jeeps, for instance -- while facilitating some truly mammoth gaming contracts. "I think, truly, down in my heart," Billie says now, "that without Robb, a lot of the things the tribe has today may not have come."
For almost two years, at least, Tiller was making upward of 30 grand a month. Then contract disputes arose with investors whom he had introduced to the tribe. But his hoped-for, much larger cut of the big action never came, even after his uncanny blend of imagination, connections, and bullshit artistry helped nurture Seminole gambling from the modest bingo-parlor days of the early '80s to the six-gaming-hall, $400-million-annual-revenue empire of today. His experience with Billie and the tribe provides a rare glimpse into the early days of America's first Native American gambling venture and illustrates just how far even a small-timer can fall when he tangles with billion-dollar forces.
Tiller's a friendly guy, articulate, quick with a joke. But get him talking about his ruin and he speaks louder, faster. His pleasant Southern inflection, which is usually just a glaze, becomes ham-hock gravy. "Bubba, do you understand how bad I am?" he says, sarcastically. "I'm the guy who fucked the Indians. I'm a guy who's a hanger-on. I'm the guy that murdered people. I'm the guy that stole bulletproof vests. I'm the guy that sold them Chinese Jeeps that didn't run. I'm a bad-ass motherfucker, Bubba. Ask around. They'll tell you. 'Oh, that goddamned Tiller's ruthless. Married a communist. We think he's laundering money for James Billie. '"
Then he returns to reality: "They've fucked me so goddamned bad, man. I've never gotten unemployment. Never gotten Social Security. Never gotten a check from the Marine Corps. Never got a check from the Indians. Come on, man. It's been a mother fucker."
He's a peculiar cracker bogeyman, this Tiller. He has friends around Palm Beach and Broward counties who love him. "He's funnier than a monkey," laughs one, Flavy Todd, a real estate agent in Pahokee, a no-McDonald's burg on Lake Okeechobee. Various other associates view him as the ghost of business deals past, a big talker, a fast mover, a doer, a thinker, a name-dropper who will help out anyone in need, especially the poor or disabled, but whose imagination handily outpaces his deeds. Just the mention of Tiller's name draws skepticism from Barry Hornbein, a Tallahassee lobbyist who has represented the Seminole for 28 years. "Tiller was one of those guys who brought a lot of deals in, and I don't think he was looked at very favorably by many members of the tribe," he says. "Whenever you saw James, Tiller was always with him. I think a lot of what he says is just stories. I'd watch what I print."
It's next to impossible to check Tiller's description of his early life. He says he was born in Baltimore and lived in orphanages as far back as he can remember. "Whenever a Cadillac or Buick would come through, I'd comb my hair and say 'Yes, ma'am' and 'No, ma'am,'" he recalls. "Whenever a Chevy or a Ford come through, I'd pick my nose, scratch myself. I didn't want to go with them people. They weren't gonna buy me nothing, man."
A family by the name of Brown adopted him, he says. The father, Oliver Brown, died when Tiller was a toddler. Then Sidney London came calling (driving a Buick convertible), but "I couldn't stand him," Tiller says. London died. Finally, Reginald Tiller adopted Robb, but the boy ran away at age 13 and for a spell lived in a '47 Chevy behind a gas station in Virginia.
Tiller didn't finish high school because, he claims, he ran like hell when it was discovered he was boffing a 21-year-old teacher. He forged parental signatures in order to join the Marines and quickly took to the institution, shining his shoes, pressing his dress blues. He expected an easy time until he was sent, petrified, to serve aboard two ships that were among those that blockaded Cuba during the eponymous missile crisis in October 1961.
A stint working consulate security for the State Department followed in 1962, he recalls, though the department's personnel files don't go back far enough to verify this. He was revved when an instructor promised him an assignment on the world's largest beach but disappointed when it turned out to be in Dhahran, Saudi Arabia, where, he says, he was greeted by a camel pissing on an airport building. During that time, he developed a knack for smuggling sugar into rafters to concoct whiskey. "God damn, I can make some sadiki juice, Bubba," he says proudly. "Everybody in the embassy was drunk, and there was no liquor allowed."
Next, Tiller contends, came an assignment in Katmandu, Nepal, where he damned near froze his nuts off as he marked time, leading a scout troop and learning tennis to provide an opponent for the ambassador, Henry Stebbins.
After he received an honorable discharge from the Marines in 1965 (release papers verify this), he foundered. He returned to the states and ran a gas station in Virginia, then a North Carolina hobby shop. The beach romp flick Where the Boys Are convinced him Fort Lauderdale was where the girls would be, and starting in 1977, state records pick up Tiller's trail with the businesses he began around Fort Lauderdale: a yacht club, a rickshaw company, a firm that put fancy steering wheels in cars.
In 1982, he was schmoozing sugar-cane money in Pahokee when he took it upon himself to gather hoopla for the town's 60th anniversary celebration. Carmen Salvatore, who was the town's police chief at the time, says Tiller "wasn't in charge" of the festivities, but Tiller contends he was responsible for appearances by five military branches and a hot air balloon race. Upon learning that pahokee is a Seminole word, Tiller says, he phoned the tribe to invite them to perform a mock raid. Tiller describes the parade that followed like the product of Vegas spawning with Fort Bragg, but a videotape of the event shows hot air balloons and a M.A.S.H. -like helicopter amid a small-time mix of school marching bands and floats from which people threw heads of lettuce to the crowd.
In any case, the Seminole didn't disappoint. "They had these rough fuckin' ponies, and when they did the raiding party, they looked like a raiding party," Tiller says. "They had war paint on, the whole thing. Tell you the truth, I thought they were actually raiding. I forgot I put this thing on, and I go, 'Holy fuck, the Indians are coming. '" Leading the raiding party was the tribe's chairman of three years, James Billie. Tiller and Billie talked, joked, laughed. Billie mentioned this bingo thing he was working. Tiller thought it was a grade-school waste of time until he saw that the Hollywood parlor was issuing five-figure jackpots.
Billie today is a robust 60-year-old with a white crew cut and an ample paunch. After a 2001 ouster as the tribe's chairman, he began earning a living as a chickee-hut builder. "Robb is a sweetheart," Billie says in a Wilton Manors backyard as two of his crewmen replace a chickee's palm fronds. "Love that guy, but there are certain things he does that irk the crap out of me. Trouble with his bullshit is that it's for real, half the time. Most of the time, he's telling the damned truth."
It's the afternoon of September 29 in the Seminole Tribal headquarters, and five council members line an imposing dais, clad variously in plaid and cowboy hats and, in the case of Roger Smith and David Cypress, Texas-hold-'em black sunglasses. Behind them in auditorium-style government chambers is a massive tribal seal; before them sit hundreds of Seminole, many dressed in jeans and athletic jerseys. At issue is a resolution that would raise the amount each of the 3,500 or so tribal members receives from gambling and other profits. Today, each person receives $3,500 a month. Under the proposal, that would rise to $4,500.
About 15 minutes into the meeting, Carl Baxley, a heavyset former councilman, approaches the microphone. "In the last meeting, we found out from Roger that you guys are getting paid $4,000 a week," Baxley says in his kettle-drum baritone. "Then I found out, that's take-home pay." Someone in the crowd whistles in astonishment. "My question is, how in the hell do you justify paying yourselves those kind of salaries?" The assembled tribal members cheer and clap as the councilmen maintain their poker faces.
The rancor indicates how quickly the tribe has had to come to terms with its financial juggernaut. When you see the Seminole tribe's garish, recently opened Hard Rock gambling temples in Hollywood or Tampa, it's hard to imagine that 25 years ago, the tribe was running nothing more than jury-rigged bingo operations in Hollywood that then-Chairman Howard Tommie began in 1971.
Back in the early 1980s, then-Broward County Sheriff Bob Butterworth tried to shut down the bingo operations, alleging that their existence violated state antigambling laws. The Seminole sued, saying they were a sovereign nation, and in 1981, the Fifth Circuit Court of Appeal upheld the tribe's claim. Ever since, gaming has filled the war chest.
But income was modest in the early years, and the Seminole needed investors, so Tiller volunteered. The first project for which Tiller hunted money was a 25,000-square-foot bingo hall in Auburn, Washington, that the Seminole tribe helped start for the Muckleshoot tribe. It opened in 1987 and survives today, still offering a $2 senior discount four nights a week.
Keeping up with James Billie brought its perils. When it appeared that Congress might impinge on Indian gaming in 1983, Tiller and Billie lugged a gator to Washington, D.C., where they played the poor-Indian card for legislators. The tribal chairman burst into a Senate gathering wearing a loincloth and tackled the gator while Tiller made overtures to every politician he met about what a damned shame it was that the Indians had to rassle alligators to make a living -- even as the Protestants, Catholics, and Jews played bingo. The pair got into real trouble later when Tiller suggested that a Holiday Inn maid get something from their bathroom... while the beast was loose on the tile. They had to talk their way out of charges that they transported a protected species across state lines.
Billie generally confirms the story -- then adds that Tiller spun a lot of tales about him. "By the time he got through with me, women would be drooling. I thought, what the fuck are they looking at? My dick's only two inches, not eight feet long. God damn."
The two men grew to be chums, running buddies. Tiller dubbed Billie "Paw Paw," as one might call a grandfather. Billie dubbed Tiller "Chief Walking Eagle," because he was too full of shit to fly. This is what passed for affection.
"You have to realize, James Billie is a lot like Robb Tiller," says Jim Kincade, a Phoenix businessman who has worked on and off with Tiller for 30 years. "I sat back and watched them butt heads. It was a handful -- and energy, they both had so much energy."
The take-no-shit tales are multitudinous, but Billie disputes a Tiller assertion that the chairman shot down a plane full of cocaine. "I never did that," he says. Rather, a plane landed on a stretch of reservation road, prompting Billie to call the cops, who in trying to cripple the craft blew apart the pilot's head. "I saw it," Billie says. "Cheese all over the damned place." Still, the wider picture that emerged during the heady, fast-growing days was that normal rules of engagement didn't apply to the Seminole, least of all to Billie, who confiscated the plane and flew it around the country. "If I followed all the rules," he says, "they would never have let me do bingo."
In late 1983, Billie slew a panther on the Big Cypress reservation with Tiller and a couple of other friends along. The following morning, Billie recalls, wildlife officials came to question witnesses. While others slinked out, Tiller raked the yard and played dumb. "Nobody ever questioned Robb Tiller, and he was right there," Billie says. It was a feat to avoid the shitstorm that followed. Billie fought what turned into a protracted legal battle that became a nationwide cause célèbre for Native Americans concerned about their tribal sovereignty. Time, the Economist, and the New York Times all covered the case before a jury in 1987 acquitted Billie, saying the state never proved that the dead big cat was definitely a panther.
"I guess we were kind of bizarre," Tiller muses. "Me holding the flashlight while he killed the panther ain't normal. OK, it ain't normal. Landing on the street in an airplane and having the police block traffic, it ain't normal. Taking an alligator to the United States Senate floor, it ain't normal."
In 1985, Tiller set about gathering investors for bingo halls in Red Rock, Oklahoma, for the Otoe-Missouri tribe and in Colusa, California, for the Wintun tribe. He also began looking for folks to put money into a South Florida Seminole bingo hall. The night it opened, in 1987, Big Cypress Million Dollar Bingo gave away $900,000, according to an Associated Press account. "If it hadn't been for Robb, those bingo halls never would have happened," Kincade says. Tiller's role generally was to get the people in place and get out of the way, but Kincade remembers that he also had a flair for gonzo promotions. One night, Tiller promised a freezer full of beef to a bingo winner, and then, when the game was over, led a live cow into the hall.
Billie recalls a commercial flight when an attendant approached and asked him if he'd like to come to the cabin. There, the pilot greeted Billie and handed him a phone receiver. To this day, the former chairman doesn't know how Tiller talked his way onto the other end of the line: Hey, Bubba!
"There is no way in hell an average citizen can do that," Billie says, marveling. "Robb's the kind of guy that could have God and the devil or Jesus and the devil arm-wrestling and laughing their asses off.
"He often told me, if he died, would I bury him? I said, 'Hell, yeah,' I'd bury him. That part I've often wondered about, if he was serious. If he died, where's he going to be buried? Who's going to claim him?"
Though Tiller and Billie were close, their friendship was tenuous; consider this episode around the end of 1985: Billie, Tiller, and Damon Smith -- a Tallahassee lobbyist and confidant of then-Florida Gov. Lawton Chiles -- rented a skiff to go snorkeling off Paradise Island in the Bahamas. Billie and Smith hopped into the drink with their snorkels in the midafternoon. Then, Tiller took the boat back to the island.
Tiller says Billie sent him away to see whether Smith, who was just breaking in with the Seminole tribe, could swim back. "That was just James," Tiller says. "He played jokes like that on people all the time. He wanted to see how tough and macho they were."
Billie says Tiller had forgotten his snorkeling equipment. Smith, like any sensible person caught in the middle of a family feud, declined comment.
One thing's clear. Tiller didn't return. Billie and Smith swam half a mile toward land before hailing a boat that took them ashore. They found Tiller in the hotel room where the men were staying. "If he could do that to us on simple shit, what else is going to happen on the real shit?" the former chairman says. "After that, I didn't have that trust with him anymore."
They still worked together, though. The pair joined forces in a lobster-trapping business that never made a dime -- and remained on solid terms until Tiller's Waterloo: soliciting capitalists Gary Fears and George Straub to finance a bingo hall in Coconut Creek.
Between January 1994 and October 1995, court documents show, the Fears-backed Gaming Management International paid Tiller $30,000 a month for "consulting services," which Tiller says was just another term for putting the deal together. An employment contract dated March 13, 1995, and signed by GMI president Harold Gray offered Tiller $600,000 a year, life insurance, four weeks of vacation, health benefits, and a leased car.
Then Straub entered the picture, and Tiller was out. A memo from Fears to Straub, dated October 25, 1995, described a seven-year contract between Fears' company and the Seminole to run the Coconut Creek casino and included the line, "Our cooperation will reduce Tiller's role, if not eliminate it." There was significant money involved. Straub offered Tiller $3 million at one point just to get lost, according to Billie, Tiller, and depositions. Billie says he was shocked when Tiller turned down the buyout. "He says, 'I want more than that,'" Billie says of his old associate. "He has fucked himself out of at least 20 deals that I know of."
The first week of November 1995, Tiller sued Fears and Straub. They sued him right back -- not for money but for a judgment affirming that Tiller was indeed a bum. The countersuit was served to Tiller at his houseboat, Horsin' Around, which was docked west of Interstate 95 in Fort Lauderdale.
Tiller claimed that Fears' company squeezed him out. Fears' Gaming Management argued that the documents Tiller produced weren't legally binding contracts and cited fraud on Tiller's part. He convinced William Scherer, one of Broward County's most prominent lawyers and a Republican heavyweight, to take the case -- on contingency, Tiller says. Scherer did not return phone messages seeking comment.
A month or so after he filed the suit, Tiller, embattled in court and in possession of a monster speed boat that Las Vegas gambling maven William Bennett had loaned him, invited Billie to set a world record: fastest round trip from South Florida to Cuba. The plan was to motor from Fort Lauderdale across the Atlantic waters, handily outrace the planes that patrol Cuba's coast, have Billie dash onto shore to plant a Seminole Tribe of Florida flag in Cuba -- à la Columbus discovering America -- and haul ass back to the continent.
Tiller was so giddy that he painted his and Billie's names on the side of the boat and told everyone he knew about the trip. Billie, however, got cold feet. He told Tiller then, and acknowledges today, that he didn't want to take the risk. Tiller scoffed, then argued, then pleaded. Billie nevertheless declined. "Cuba, he can do that," the ex-chairman says. "I can't do that because I'm in a different type of political situation."
Tiller says he was not in the mood to lose any more face, so he set sail at the end of 1995. He describes the following trip, the particulars of which can't be confirmed: He varnished Billie's name off the boat, loaded up a box load of Victoria's Secret bras and panties for later purposes of seduction, duct-taped a bulletproof vest onto his yellow Labrador, and set out across rough seas. Halfway there, patrol planes told him over the radio to slow his aircraft (the boat was moving so fast), but Tiller zipped into Havana, where he says he kept one hand in the air until he was satisfied he wouldn't be shot. His dog's paws were bloody from skidding around the boat, he was petrified, and unmentionables were scattered around the deck as he pulled past gawkers into the harbor. "God damn," he recalls, "they thought I was from another planet." As a show of goodwill, he passed out panties and "Re-elect James Billie" T-shirts to the agents at the harbor.
"They said, 'What do you want?'" Tiller says. "I said, 'Cigars, pussy, and rum.' They said, 'Welcome to Havana. '"
Tiller declines to say exactly how long he stayed in Cuba but acknowledges it was a matter of months -- enough time to fall in love with and marry a pretty brunet less than half his age, Isbet, who lives with him still. Upon returning stateside, he went to the Keys to visit Billie, who, to Tiller's deep chagrin, was hanging out with George Straub. "James couldn't even look me in the face," Tiller says.
The court battle continued and was as acidic as it was glib. A typical exchange from a 1996 deposition:
Tiller: Straub has a brother; the brother has a secretary. The secretary has been talking to a friend of mine telling me the discussions regarding Straub's businesses. One of those discussions was how he was going to screw Tiller.
Attorney Joseph Coates: OK. When were these discussions?
Tiller: Prior to him screwing Tiller.
Billie's deposition in the case makes clear that he didn't appreciate questions about his personal life and Seminole business. Further poisoning Tiller's relations with tribal members was a protracted and ultimately misguided St. Petersburg Times investigation into Billie and the Seminole tribe's businesses. A September 1997 Seminole Tribune series fingers Tiller as "the 'main source' for all the damaging information -- both from the flamboyant lawsuit he had filed and from interviews with reporters [Jeff] Testerman and [Brad] Goldstein."
Pete Gallagher, a freelance writer living in Tampa, wrote the Tribune stories and says today that it wasn't an act of treason when Tiller talked to Testerman. "He is an exhibitionist," Gallagher says. "He wants attention. He was making all kinds of money bringing people to Jim Billie. And the people he was bringing to Jim Billie could have just walked up and knocked on his door. There was no scheme that was too big. If Tiller heard Disneyland was for sale, he'd be trying to bring the Seminoles in to get part of it."
Tiller, who blames Straub for sparking the investigation, earned a few paragraphs' mention in the subsequent Times series, for selling the tribe $2,500 non-road-legal but functional Chinese Jeeps that wound up as tour vehicles at Billie Swamp Safari in Clewiston. He also took flak for purchasing 60 bulletproof jackets, allegedly on the Tribe's behalf, that he wound up donating to police departments. (The Palm Beach force, for one, confirms receipt.) Billie's printed quote on Tiller: "We have a saying. He's the kind of guy who could fall in a barrel full of tits and come out sucking his thumb."
"What really hurt the worst," Tiller says, "is when James said I was nothing, I just kind of hung around, like beggin' for scrap food. And here all that time, I thought I was his best friend. I brought them investors. And then he turned on me and started all those rumors and all that bad stuff -- for what? I'm nobody."
The action had evaporated. Tax records illustrate how hard up he was: the feds hit him with a $15,705 lien in February of 1998. Four months later, Scherer dropped Tiller's case. Chief Walking Eagle was broke and relied on friends for places to stay. But he remained confident about winning the lawsuit. Then in 2001, Tiller was helping a friend move aviation equipment atop a tractor-trailer in Fort Myers when a tarp he was pulling ripped and he fell to the ground. "I couldn't walk for quite a long time there," he says. "My poor wife went through hell. We bummed from everybody on the planet Earth for therapy, for medicine, for help." He finally got some physical therapy and massive amounts of ibuprofen at the Bay Pines Veterans Affairs Medical Center, north of Tampa. His legal situation, meanwhile, did not improve. In 2002, a judge dismissed his suit; another judge upheld Straub's claim that Tiller was in breach of contract; Tiller's appeal was denied.
Dennis Wells, who represented Tiller on contingency for the last two years of his suits, acknowledges he took on an uphill project. "We were claiming he was supposed to get a percentage of casino revenues," the Orlando attorney says. "It could have been lots of money."
Tiller was plumb busted. Today, his files, photographs, and documents are packed into beat-up trucks and trailers outside his RV. The past for him is a recurring fever dream that he never expected to lead to this future. "I'm just a simple, plain, poor white boy who was trying to borrow money to get a piece of the action," he says of his days near the tribe. "And plus, I really liked the Indian people a lot, I really started liking them, because I felt they liked me. But I guess like [Billie] says, I was nothing but a camp robin hanging on.
"People remember, and then they go, 'God, what happened to you? You was a real guy. You were the brains of this operation. Robb, you've got to be a billionaire.' Shit. We couldn't even get financing on a car, man. On a car. On a car."
Last month, Tiller was back on the world's largest beach, this time in Qatar, on an errand to sell bottled water. "The people are nowhere near what you read about, what you hear about," he says. "You picture people with their ears cut off and fights and all the rest." The country sits on some of the world's largest proven natural gas reserves, which Tiller would like to help sell. To that end, he displays glossy literature on Qatar's horses and refineries. He claims that he talked his way into meetings with the Qatar royal family, whom he met through contacts from a camel race that he attended. When New Times seeks verification, he says he does not want to provide contact information for the people in Qatar he's dealing with. The whole yarn sounds grossly implausible until you recall the words of James Billie: "If I wanted to meet somebody today and I didn't know how to meet him, I wouldn't hesitate to call Robb. Somehow, he would get them."
Anyway, long story short, Tiller believes he could soon become a natural gas magnate. This scenario assumes he can reverse his decade-long skein of business meltdowns. Tiller's friend Flavy Todd, in Pahokee, describes an aborted venture in which Tiller approached a capitalist about starting an airline. "The next thing you know, he cut Robb off," Todd says. "Robb had put the whole thing together. I was with him through the whole thing. This is the way big business deals work, I guess. I try to urge him in these deals to get good attorneys."
Billie describes Tiller's proclivity for getting steamrolled ("He would land deals. Good deals. And fuck 'em up."), but as he ponders his own attempted comeback, he imagines a reunion with his old associate. "I'm pretty sure he and I, by his thinking and my bullshit, we'd probably be millionaires again by next year," Billie says. "I'll call Robb Tiller again. Tell him we need to make some money before he kicks out on me. And he still needs somebody to bury him."
