When Raj Rajaratnam was a hedge fund baron managing billions of dollars and being lionized as one of Wall Streets savviest investors, he was asked what made him so successful. “It is pride, and I want to win,” said Mr. Rajaratnam, the co-founder of the Galleon Group hedge fund, according to the 2001 book “The New Investment Superstars,” by Lois Peltz. “I want to win every time. Taking calculated risks gets my adrenaline pumping.” A decade later, Mr. Rajaratnam is taking the biggest calculated risk of his life. Beginning Tuesday, he will be seated at the defense table in a federal courtroom in Manhattan. In the biggest insider trading trial in a generation, Mr. Rajaratnam, 53, is fighting charges that he made $45 million trading on illegal stock tips. If a jury convicts Mr. Rajaratnam, he faces up to 20 years in prison. - PETER LATTMAN