Chief Walking Eagle

Robb Tiller went from rags to riches and right back after 15 years spinning deals around the Seminole

Robb Tiller spent the night of Hurricane Jeanne doing what he has done for most of his 62 years -- trying not to lose his ass. Every hour, as 130-mph gusts raked the grassy shore of Lake Okeechobee where his three-decade-old, amphibious Lake LA-4 airplane was staked to the ground, the once-and-aspiring somebody trudged outside in his rubber waders and military poncho. Sometimes, the gale was so strong that he had to tie a rope around his waist and secure it tree to tree as he half-crawled, half-staggered to the plane, which was parked about 100 feet from the cluttered diesel Mountain Air RV that he calls home.

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."

"Trouble with his bullshit is that it's for real, half the time. Most of the time, he's telling the damned truth."
W. Kelley Lucas
"Trouble with his bullshit is that it's for real, half the time. Most of the time, he's telling the damned truth."
As the Seminole chairman, James Billie (pictured) long trusted Robb Tiller as a friend and as an informal business partner.
As the Seminole chairman, James Billie (pictured) long trusted Robb Tiller as a friend and as an informal business partner.

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."

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