It all started when Matthews reportedly purloined an alleged $5 million from his then-fiancée, the daughter of the inventor of Rollerblades. Matthews parlayed his ill-gotten gains into a real estate empire that would ultimately enrich him while causing financial and personal disaster to those around him. Style and a flair for the dramatic were Matthews’ stock and trade, and he would leave those who were not wise to his ways often breathless and in awe.

As a young real estate developer, he once rented a helicopter and landed on the lawn of the city hall in Waterbury, Connecticut, to meet the mayor and discuss ways in which he could help revitalize the small town. Mayor Joseph Santopietro would ultimately be imprisoned on corruption charges, a fate other politicians met after their dealings with Matthews. With his firm handshake, hand-tailored suits and Tony Robbins-like energy, Matthews had a personality that could fill a room and mesmerize a crowd. Having worked his way up from a small-town mayor to the governor of Connecticut, Matthews became a major landlord to the state with sweetheart deals that defied economic reason. His newly found wealth put him in large homes but also put the Connecticut governor in the “big house” in which he served time in federal prison for his questionable dealings with Matthews. But Matthews’ impact on the lives of those who became entangled in his world would only worsen.

In an audacious and spectacular attempt to score big, Matthews bought a stolen copy of the Bill of Rights for $200,000 and then tried to flip it for a $5 million profit. After being hounded by the FBI, Matthews had to give up his dream of converting the document into fast cash, but according to those in the know, he ended up causing the heart attack death of his partner and well-known Nantucket art dealer, Wayne Pratt. The details surrounding Matthews’ purchase and ultimate sale of the document to a Washington museum read like a John le Carré novel and painted a picture of a person whose fearless brashness knew no limits.

After surviving his near brush with death, he once brought a group of Tibetan monks to his home, so he might seek some type of cosmic redemption. The monks performed their ritual sand mandala, whereby they create magnificent designs out of sand, and proceeded to take the finished work of art and empty it into the sea in a statement that life is about the experience and not the material. Having totally missed their message, Matthews took out a wad of cash from his pocket and begged the monks to have their creation sealed in polyurethane instead so he could permanently hang it on the wall. The juxtaposition of the spiritual monks sitting in Matthews’ lavish living room was striking, and one could only wonder what went through their minds as they pulled away from his highly leveraged home.

One of Matthews’ most spectacular acts of deception on Nantucket was his $40 million loan from Deutsche Bank to develop his Point Breeze Hotel and Club, which was to feature internationally known singing artists to entertain his members as they would dine on lobster tails and oysters. Having sold memberships in the hotel by telling prospects he had secured commitments from major players on the island, Matthews began to believe in his own dreams. The hotel was never finished, and the $40 million bank investment largely vanished into a $2.8 million foreclosure sale to the owners of the new Nantucket Hotel.

The Point Breeze collapse did not stop Matthews but instead seemed to motivate him to show the world that he was unaffected by the financial loss associated with his latest questionable venture. He decided to throw a fiftieth birthday party for himself at his Palm Beach home, Casa Bendita, with the theme of “Arabian Nights.” Arriving at the door of his 20,000 square-foot oceanfront villa, guests were greeted by belly dancers sitting atop live camels flanked on either side of a six-foot-wide, hand carved mahogany door. Entering the resplendent home, guests were ushered to the backyard and into a 5,000 square-foot maroon tent replete with oriental rugs, velvet sofas, hookah bars and exotic food stations. Entertainer Jim Belushi performed on stage in front of 350 of Matthews’ closest friends. The only people who were disgruntled over the spectacular $500,000 event were the caterers, bartenders and animal handlers, who according to reports in the Palm Beach Post, sued Matthews for nonpayment.

On a glorious sunny Palm Beach day, federal authorities converged on Casa Bendita and arrested Matthews, who might soon be exchanging his fine-tailored clothing for an orange jumpsuit and an ankle bracelet. The 151-foot yacht he allegedly purchased courtesy of the Chinese investors and the collection of Rolls-Royces in his garage became instantly irrelevant.

On April 25th, Matthews pleaded guilty to conspiracy, money laundering and tax evasion. He was charged with twenty-one counts in an indictment that also brought charges against his wife and his business partners. In part, Matthews was charged with defrauding at least sixty foreign investors from China and Iran by way of the Federal EB-5 Visa program that he promised would provide them with a path to a Green Card. Additional details about the elaborate fraud emerged in the press, revealing that the investors were told that Donald Trump and Bill Clinton were advisors on the project, though that too was a lie. Ironically, those who invested in Matthews in search of economic freedom may have been the final straw in Matthews losing his.

There are those who have followed Matthews’ career who are convinced that he will once again escape prosecution in his Houdini-like tradition and yet again perform his special magic on federal authorities. But this time, he may have indeed pulled the last rabbit out of his hat, the final act in one of the most colorful white-collar criminal careers Nantucket has ever seen