By Francisco Alvarado
By Trevor Bach
By Chris Joseph
By Michael E. Miller
By Allie Conti
By Keegan Hamilton and Francisco Alvarado
By Jake Rossen
By Allie Conti
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.