Boone Pickens arched his left eyebrow into a silvery horseshoe and waited to hear exactly how much personal income he had earned the previous year. It was two days after Christmas in 2006, and he was dressed down in khaki slacks, a gray sweater, and a pair of loafers, which he had propped up on the desk in his Dallas office.

Pickens turned to check the computer screen behind his desk. Except for his thinning gray hair and the flesh-color hearing aids in his ears, he looked as lean and mean as he had in the 1980s, when his exploits as a corporate raider shook Wall Street and catapulted him onto the covers of Time and Fortune.

Since then, Pickens has endured a two-decade roller-coaster ride. In 1996, slumping natural-gas prices led to his ouster from Mesa Petroleum, once the nation’s largest independent oil company. The following year, he founded the energy hedge fund BP Capital. But even as he launched his financial recovery, his personal life had been shattered by two divorces and a continuing series of crises involving his two sons.

Jay Rosser, Pickens’ veteran public-relations aide, returned from an adjacent office with the 2005 personal-income figure his boss had requested. “You made $1.504 billion last year,” he reported. “That’s adjusted gross income?” Pickens asked.