Michael M. Thomas, a former investment banker and a novelist of Wall Street manners, said that if he were ever to write a book about his own privileged upbringing, he would title it “Orphans With Parents.” Meaning that despite the private clubs, the best schools and all the many things that money can buy, there has always been for those born into this world a sense of acute loneliness that can strain ties with parents and mark a child forever.

Of course, in the case of the younger Mr. Gilbert, there was much more to it than that. According to people who knew him, he had numerous psychiatric maladies and for years had received various forms of counseling and medication.

Nevertheless, said Mr. Thomas, who did not know the family, even though Tommy was born into a culture that “disdained money,” he soon found himself in a world that, much more so than in his father’s time, had come to worship it.

“That can put you in a weird place,” Mr. Thomas said.

The Gilberts had money, of course. Mr. Gilbert, the father, had a weekend home in East Hampton’s exclusive Georgica Association enclave, and he was the sole owner of his newly established hedge fund, Wainscott Capital Partners, named after another Hamptons neighborhood.

Still, he was no magnate, as the size of his $1.6 million will attests. Beneficiaries include his wife; his 24-year-old daughter, Clare, an aspiring writer who has a book-themed blog; and his son. Whether Mr. Gilbert will be able to collect or not depends on the ultimate resolution of the criminal charges, lawyers say.

About a third of Mr. Gilbert’s estate comprised his hedge fund stake, with the remainder being other investments, property and cash.