From the disco he would move to the sauna, the only one ever known to have been built on board an aircraft, and then to his private bedroom. Perchance to dream of his rise from metal shaper in a Detroit car factory, as the grandson of Slovenian and Italian immigrants, to one of the world's wealthiest men at 35.
Mr Vesco is now 60, and he has traded his favoured red velvet smoking jackets for a grey prison uniform in the Cuban state security prison, Villa Marista, in Havana. Awaiting verdict and sentencing on charges of economic fraud against the Castro regime, he could be in jail until he is 80, but at least, say diplomats, he is too old and ailing to be sent to one of the Caribbean island's notorious forced labour camps. In those, able-bodied prisoners are forced to cut sugar cane, barefoot, for 12 hours a day in blistering sun, according to human rights groups. A panel of five judges will decide whether Mr Vesco abused the Cuban state pharmaceutical industry by developing a would-be "miracle drug" - supposed to cure cancer, Aids and herpes and add years, perhaps decades, to a person's life by boosting the immune system - behind the government's back. He told the court the Cuban authorities were involved in the research for the drug, known as TX or Trioxidal.
According to Donald "Don-Don" Nixon, nephew of the late president and a long-time friend of Mr Vesco who was detained with him in Havana in May last year but later released, even relatives of Cuba's president, Fidel Castro, were involved in the research and test production at the state-run Labiofam lab in Havana. Mr Nixon described the drug as "the biggest breakthrough in the history of man, worth one billion dollars a month net" and said it had cured his own wife's cancer.
Once nicknamed "Swifty" or "Rapid Robert" by business associates because of the speed with which he could multiply his assets as well as the fast life he led, Mr Vesco has spent the last quarter century fleeing American justice. He was the "White Knight" who in 1970 "rescued" the late Bernie Cornfeld's Geneva-based Investors' Overseas Services, which asked: "Do You Sincerely Want to be Rich?" and promised: "I'll make you a millionaire."
Tempting small investors, IOS had become one of the world's biggest financial groups in the 1960s, but by 1970 it seemed on the brink of collapse, despite still controlling $400m (now pounds 258m) in funds. For $5m, "Swifty" took control of a financial hall of mirrors that was to push him into Fortune magazine's list of the world's wealthiest men, but would ultimately force him to live on the run.
While Mr Vesco was buying the plane and the $1.3m yacht, investors began noticing their returns were rapidly diminishing. Their concern deepened when they could not discover where their money was invested. The Securities and Exchange Commission found in 1972 that at least $224m of investors' money had vanished, presumably into Mr Vesco's own accounts. It charged him with fraud, and he became a fugitive. The custom-fitted Boeing 707, described as more luxurious than the US President's Air Force One, was impounded and eventually bought by Imelda Marcos, who was reported to have outbid Elvis Presley and Mick Jagger.
Mr Vesco flitted between the Bahamas, Costa Rica and Nicaragua until settling in Cuba in 1982, where President Castro accepted him "for humanitarian reasons". Calling himself Tom Adams, and living in Havana, close to Mr Castro's own mansion, he was known to neighbours as Tom el Americano.
His security appeared second only to that of el Jefe Maximo himself, with two carloads of heavily armed men following him everywhere and half a dozen extra "caddies" on the golf course. Whether the state-paid heavies meant he was friendly with President Castro was never clear, but in court last week Mr Vesco said he had never met the Cuban leader.
Diplomats at the US Interests Section in Havana said last week that Washington was still "interested" in having Mr Vesco extradited. Since the IOS money has probably evaporated, the most important charge would be one by the state of Florida that he helped to organise a "bridge" in Cuba for cocaine flights by the Medellin cartel from Colombia to the United States.
Carlos Lehder, a former Medellin cartel chief now in jail in the US, testified that Mr Vesco had acted as a middleman for cocaine shipments. Lehder's pilot, Carlos Fernando Arenas, also in jail, testified that Mr Castro's brother Raul, Cuban defence minister, met him and Mr Vesco to discuss the arrangement. Other sources said that Cuba used the returning cocaine planes to fly weapons to guerrillas of the pro-Cuba M-19 group in Colombia.
When the financier was arrested at his home last year, the Cuban authorities said he would face charges of being a "provocateur" and "an agent of foreign powers". By the time the court case started last week - it ended after three days - those charges had been dropped, and Mr Vesco was accused only of economic fraud centring on the "miracle drug". His second wife, Lidia Alfonso, a Cuban, faced similar charges.
Many diplomats in Havana believe the fraud charges may have been a smokescreen by Mr Castro to keep Mr Vesco behind bars, where he cannot talk. Some believe "Swifty" had planned to flee Cuba, perhaps to reveal what he knew of alleged Cuban involvement in drug trafficking. Others believe the trial is a battle for control of the drug TX in case its "miracle" properties prove to be true.
If Mr Vesco is convicted, his four children from his first marriage believe he will die in jail. In court, the 6ft 1in former owner of Silver Phyllis appeared to weigh around nine stone, almost six stone less than in his 1970s heyday. "We are worried about his health," his son Danny said. "We hope the Cubans will be compassionate with him."