On paper, Pearlman certainly looked like a successful serial entrepreneur, but his earnings statements contained more hot air than his first venture, a blimp company which made most of its money by suing for insurance claims after accidents. He later branched out into a helicopter commuter service and a transcontinental airline which never owned an operating plane (ads for its service depicted a model plane held in front of JFK Airport), but reaped huge profits by selling a fake retirement plan, a Ponzi scheme smaller than Bernie Madoff's recently revealed scam, but even more shoddily constructed. Pearlman poured that money into his first entertainment venture, the Backstreet Boys; he spent millions launching them in Europe. When they became a hit stateside, they sued Pearlman for unpaid compensation—in their first four years, they each made just $60,000. The members of Pearlman's next group, 'N Sync, followed suit once they topped the charts.
Pearlman's saga is so bizarre that the pedophilia rumors that formed the spine of Vanity Fair's article on his arrest are the least interesting part of the tale. Tyler Gray, who covered Pearlman's foray into downtown development while working for The Orlando Sentinel, carefully sidesteps these claims for lack of evidence, but addresses through extensive, probing interviews how Pearlman managed to perpetuate his schemes for so long. Gray weighs the evidence—including Pearlman's own take, since Gray is the only journalist to speak with him in prison—and builds a fascinating but damning case against a man with Tom Sawyer's penchant for reaping the benefits of others' work, someone so desperate to keep up appearances that he still believes, in spite of his guilty plea, that he'll eventually be vindicated.
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