COMMENTARY

Peter Burgess

It was a boilerplate, how-I-spent-my-summer-vacation assignment for sixth-grader Jed S. Rakoff.

By the time he turned it in, though, what was supposed to be a five-page report about a family trip to Colonial Williamsburg swelled to 50 pages packed with unsavory stories about the Founding Fathers, such as that Benjamin Franklin cheated on his wife.

IMAGE U.S. District Judge Jed S. Rakoff, shown in his chambers, is known for his provocative opinions. Rob Bennett for The Wall Street Journal

'I was always attracted to taking a novel position,' recalls Mr. Rakoff, now a U.S. district court judge in New York, 'but one grounded in the materials I'd been given, not made up out of whole cloth.'

The 68-year-old Judge Rakoff is known for his unconventional—and often provocative—attempts to get to the bottom of the matters before him.

On Wednesday afternoon, the judge is expected to grill the Securities and Exchange Commission and Citigroup Inc. about why he should approve their proposed $285 million settlement of fraud charges over a mortgage-bond deal. He previously made the agency squirm over a 2009 deal with Bank of America Corp.

'As an institution, I think they have a very distinguished history,' Judge Rakoff says of the SEC, in an interview with The Wall Street Journal. 'That doesn't mean they're right in every case.'

Last month, Judge Rakoff demanded that SEC and Citigroup officials show up in his courtroom with answers to 18 questions about the settlement.

Judge Puts Citi and SEC in Hot Seat 'Why should the court impose a judgment in a case in which the SEC alleges a serious securities fraud, but the defendant neither admits nor denies wrongdoing?' he wrote in the order last month.

The SEC and Citigroup say the deal is fair.

In 15 years on the federal bench, Judge Rakoff has written funny, blunt and occasionally reversed opinions. In addition to pushing back against what he has described as superficial punishment by the SEC for companies accused of fraud, Judge Rakoff has overturned a death-penalty conviction and carped about U.S. sentencing guidelines.

In 2006, he ordered the government to release information about detainees at Guantanamo Bay in Cuba.

'He has always been a feisty person,' says Todd Rakoff, the judge's younger brother, a law professor at Harvard University. 'He's not at all afraid to mix things up, to put it colloquially, but I would say also that I think he really cares about getting it right, and I think he views the law as an instrument of justice.'

While Judge Rakoff has a reputation as a populist, he also rules in favor of big companies, once dismissing a class-action lawsuit against International Business Machines Corp.

In addition, last year the judge ruled that the Financial Industry Regulatory Authority and the Wall Street self-regulator's former top executive, Mary Schapiro, enjoyed immunity in a private lawsuit filed by broker-dealers. Ms. Schapiro now is chairman of the SEC.

'Rakoff supported the further entrenchment of the Wall Street-Washington incest that is crippling our society,' Larry Doyle, a former trader, wrote on his blog last year. In an interview, Mr. Doyle says: 'Up to that point, I was like: 'OK, this is the people's judge.''

The ruling was upheld on appeal. Judge Rakoff says he calls them like he sees them.

'I don't have any respect for judges who arrive at the result first, and then try to figure out some way they can bend the law to reach their particular predilections,' he says.

Married with three daughters, Judge Rakoff nurtures a theatrical flair by writing lyrics for judges performing in the annual 'Courthouse Follies' and has taken up ballroom dancing.

A late riser, he often holds court far into the evening, and can quickly alternate between cracking jokes and shredding a lawyer for slacking off.

'Welcome to my ballpark,' Judge Rakoff, a New York Yankees fan, said at an August hearing in a lawsuit by Irving Picard, the court-appointed trustee recovering money for Bernard Madoff's victims, against the New York Mets owners. The judge said he was glad to read their voluminous filings 'because otherwise I probably would have had to watch a Mets game.'

He is well-known among lawyers for showing little patience with delays and moving cases along rapidly.

In May, Judge Rakoff called a lawyer who didn't show up for a conference, putting him on a speakerphone in court. 'So why should I not dismiss this case?' the judge demanded. The lawyer blamed 'a miscommunication' and was ordered to pay his opponents' legal fees for the day.

Judge Rakoff grew up in the Germantown section of Philadelphia. His father was a gynecologist, and his mother taught English. The opportunities his mother was denied—first as a girl and later when she was a mother—highlighted problems the young Rakoff saw hidden behind a façade of tranquility in the 1950s.

'It was really from my mother that I sensed this dissonance between the sort of comfortable acceptance of a phony reality versus the true reality,' Judge Rakoff says.

In high school, he was captain of the debating team. At Swarthmore College, he was student-council president and editor of the newspaper. He toyed with becoming a reporter before pursuing a law degree at Harvard.

After working as a federal prosecutor and defense lawyer, Judge Rakoff was appointed to the bench in 1996 by President Bill Clinton.

He says he isn't hostile to the SEC and is obliged under federal law to decide if settlements are fair, reasonable and in the public interest. In a recent article in Litigation Magazine, Judge Rakoff said he 'gagged' on the SEC's original settlement with Bank of America. He was especially miffed that shareholders who had allegedly been defrauded were being asked to pay a $33 million fine related to bonuses paid in the 2008 takeover of Merrill Lynch & Co.

Judge Rakoff forced Bank of America and the SEC to come back with a 50-page statement about what happened—and a higher penalty. He reluctantly approved the revised deal, quoting 'the great American philosopher Yogi Berra' in a ruling.

The judge says he feels bad taking lawyers and others to task, but he saw in private practice how delays and gamesmanship made the American legal system too slow and expensive for the average person.

'The price of being a nice guy is too high—much too high—in terms of the system of justice,' Judge Rakoff says.

Write to Michael Rothfeld at michael.rothfeld@wsj.com