HOUSTON -- They grew up in Illinois with high-achieving older brothers, went to college in the Deep South on academic scholarships, and then moved on to Harvard.
Both have worked practically nonstop over the past two years preparing for the battle of wits unfolding as the Enron Corp. criminal trial reaches a pivotal point.
With one of the best young prosecutors at the Justice Department facing off against the former chief executive of Enron, the stakes hardly could be higher.
Sean M. Berkowitz, the 38-year-old head of the Enron Task Force, must succeed in undermining Jeffrey K. Skilling's carefully crafted testimony, or the government crackdown on white-collar crime stands to lose its biggest case. Skilling, Enron's 52-year-old former chief executive, must fend off his relentless fellow Harvard alum or face the prospect of more than a decade in prison. Neither man is accustomed to losing.
It will be a cross-examination for the books, predicted John C. Coffee Jr., a Columbia Law School professor who has tracked the case. "I think it will be long and extensive and it will make all the difference," he said. "You won't see a flash of lightning. It will be like a slow drip of water."
The outcome could well influence whether U.S. attorneys across the country continue to file complex cases targeting fraud at the nation's most powerful companies, Coffee said.
Berkowitz has said he intends to take no longer in the cross-examination, which began yesterday, than Skilling took in his direct testimony, which lasted 20-plus hours over four days.
Skilling drew on his experience as a consultant and high-flying businessman in a step-by-step rebuttal of the government's case to a generally attentive jury.
Skilling faces 28 counts of fraud, conspiracy, insider trading and lying to auditors in connection with Enron's collapse, while co-defendant Kenneth L. Lay, the company's former chairman, faces six counts of fraud and conspiracy. Lay has indicated he will testify in his own defense as well.
While Skilling was poring over thousands of documents to prepare for his performance on the witness stand, so was Berkowitz.
The trim, balding prosecutor joined the government's Enron Task Force in December 2003 from the U.S. attorney's office in Chicago, not long after securing fraud charges against the officers of Anicom Corp. - a case some have called a "baby Enron."
He took over leadership of the task force in July, and since then has supervised the eight attorneys and 10 FBI agents working with him on the trial, which opened Jan. 30.
Even so, he may be outmanned. Skilling is said to have spent more than $40 million so far on his legal defense, and Lay has contributed millions more.
And despite the prevailing view of Enron as a hotbed of fraud, the case is no slam-dunk for the youthful government legal team. It rests heavily on the testimony of executives who cut deals to shorten their likely prison time.
While the prosecution's case has gone smoothly under Berkowitz over the course of two months, it never produced a smoking gun.
"He will be a genuine superstar among lawyers if things go well, but the luster could come off pretty quickly," said veteran Chicago attorney Warren Lupel, Berkowitz's uncle and a mentor who encouraged him to pursue the law. "This is a case the government could lose."
Berkowitz usually wins. He won national debate tournaments at Glenbrook North High School, and finished first in his undergraduate class at Tulane University before attending Harvard Law School.
While still a teen, he assisted his uncle as Lupel fought on behalf of Gary Dotson, who was convicted of rape in 1979 but later was exonerated by DNA testing and by his accuser's admitting she made up the rape.
Skilling, who grew up in Aurora, Ill., also went South for college, graduating from Southern Methodist University in Dallas, before going to Harvard Business School. Skilling's older brother is chief meteorologist for the Tribune Co.'s WGN-TV in Chicago.
Like Skilling, who famously took his Enron pals on motorcycle racing trips across remote dirt roads, Berkowitz is competitive. He rides a motorcycle as well when he is not running marathons. His brother Lyle L. Berkowitz, a Chicago physician, recalls tennis matches stretching three or four hours on the hottest summer days. "Neither of us would give up," he said.
Calm and controlled inside the courtroom, Berkowitz hangs loose outside it, displaying a ready smile and twinkle in the eye. He is part-owner of Chicago's Double Door nightclub and has staunch admirers at Katten Muchin Rosenman LLP, the Chicago law firm where he worked before joining the government.
Enron has put his life on hold. He hasn't seen much of his beloved niece and nephew, his five-bedroom Chicago house or his collie-samoyed mix, Scout.
Greg Burns writes for the Chicago Tribune.