Victor Ayad, an Austin investment banker who was a schoolmate of both Pickens boys, attributes some of Mike’s acting out to the remote physical and social environment of the Texas Panhandle. “There’s something about growing up out there in the flatland that keeps you content in the desolation of a cultural void or cultivates a creative side that can sometimes go crazy,” he says. “Rich kids I knew in Houston and Dallas still conducted themselves with a certain amount of decorum in front of their parents even as they were messing up behind the scenes. The rich kids I knew in Amarillo went out of their way to be social misfits.”

Pickens finally shipped Mike off to the Schreiner Institute, a relatively permissive boarding school in central Texas. Around this time, Mike got interested in flying airplanes and started studying for his pilot’s license. He was a natural at flying, just as he was at golf and hunting.

Mike also displayed flashes of his father’s financial genius early on: He could keep track of 10 different positions in 10 different stocks without the aid of a calculator or computer program. But he had little interest in formal education. He attended four different colleges without earning a degree. According to John O’Brien, his great uncle, he also left a trail of unpaid bills. Eventually, he got a job at a Dallas brokerage firm, where he traded stock for Mesa and other accounts.

Meanwhile, Boone had embarked on a new life with a new wife and extended family. In April 1972, he married Beatrice Carr Stuart, an Oklahoma City socialite who had four children from her prior marriage. Pickens became especially fond of the youngest girl, Liz, and formally adopted her a few years later.

But Pickens’ daughters by Lynn remained distant from their father, and their youngest brother became ever more bitterly estranged. In fact, Tom had to work his way through Southern Methodist University, doing odd jobs such as driving a forklift. He started a small computer hardware firm and sold it for a tidy profit. After graduation, he showed his acumen as a financier by turning around a small closed-end fund and a savings and loan. At age 30, he arranged financing for Catalyst Energy Corp. The opening of its Louisiana plant was a gala affair presided over by then Louisiana senator Russell Long.

Tom felt as though his father managed to turn what should have been moments of joy into embarrassments. When Tom got married, friends say, Pickens wouldn’t attend the reception because Bea didn’t feel like she was seated properly. When Tom’s son was christened, Pickens was late.

Tom subsequently moved to Charleston, South Carolina, to renovate a historic-district home and start an independent capital fund, hoping he and his wife, Jennifer, could raise their children outside his father’s shadow. Unfortunately, one of the 26 investors in his fund was Dana Giacchetto, a money manager recommended by Merrill Lynch. In the course of defrauding a roster of Hollywood clients, Giacchetto allegedly invested some of their money in Tom’s fund but defaulted on repayments. Giacchetto later went to jail, and Tom returned to Texas to specialize in salvaging embattled companies.

The consensus among several longtime Pickens family friends was that Tom was unfairly victimized in the Giacchetto affair. Tom Treadwell, a former Holdenville, Oklahoma, banker who has known three generations of Pickens men, affectionately refers to Tom as “Triple.” “Tom is a fine young man,” Treadwell insists. “But Mike is a goddamn outlaw.”

For a time, Mike showed signs of cleaning up his act. Following his father’s remarriage, he got married and began to gravitate to the Boone-Bea-Liz family circle. He even posed for a photograph with Boone, his grandfather, and his newborn son, Michael Jr.

But within a few years, Mike divorced and resumed a precipitous downward spiral fueled by alcohol and drugs. After moving to the town of Nocona, Texas, on the Oklahoma border, he married again and fathered another child. Then he promoted a series of dubious financial schemes that drew the scrutiny of the I.R.S. In 1991, Boone barred Mike from managing Boone’s personal and corporate stock accounts. Evidently feeling that his son had taken advantage of him, Boone reportedly deposited a treasury check made out to Mike.