Is This Courtroom Banter Funny? You Be the Judge

NEW YORK—The trial of Rajat Gupta has all the serious elements of a high-profile white-collar case, with the former Goldman Sachs Group Inc. director facing potentially significant prison time.

It also has featured Rodney Dangerfield-type jokes. Lots of them.

When a juror had difficulty scheduling dental surgery, Mr. Gupta's lawyer, Gary Naftalis, recounted in court how a lawyer once questioned a dentist on the witness stand. "He started his cross-examination by saying, 'I want you to sit back in that witness chair and relax. My questions aren't going to hurt a bit.' "

Retorted U.S. District Judge Jed Rakoff: "Most judges…definitely feel the need for Novocain," adding: "You all know the drill."

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Rajat Gupta and Lawyer Gary Naftalis in June.

The justice system has been a form of theater since Ancient Greece. "When you get tense situations or it gets incredibly dull and boring…a little humor can lighten things up," said Lance Ito, the Los Angeles Superior Court judge who sometimes joshed with lawyers during the O.J. Simpson case.

In one trial, Henry "Pete" Putzel III remarked to a witness who had already been questioned by multiple lawyers, "I feel like Elizabeth Taylor's eighth husband on [their] wedding night," adding: "I know what I'm being asked to do and I know how to do it. I'm just at a total loss as to how to make it new and exciting."

In a 1970s organized-crime trial, the late Norman Ostrow cross-examined Jimmy "The Weasel" Frattiano, a government cooperator who had admitted to a number of grisly murders. As Mr. Ostrow prepared to conclude, Mr. Frattiano confirmed that under his deal with the government, he was about to be set free.

"You don't know who I am, do you?" the lawyer asked.

"No," Mr. Frattiano replied.

"Good, let's keep it that way," Mr. Ostrow quipped, and walked away.

The trial ended in a hung jury.

The minor league stand-up comedy routine during Mr. Gupta's insider-trading trial has featured Judge Rakoff and Mr. Naftalis, who have been friends for decades. The two prosecutors have served as straight men since the first day. Assistant U.S. Attorney Reed Brodsky sought assurance Mr. Naftalis wouldn't be able to mention many of the charitable endeavors of Mr. Gupta, who has pleaded not guilty to insider trading.

"Your Honor, just to be clear, he won't mention AIDS, malaria or tuberculosis," Mr. Brodsky said.

"Or bubonic plague," replied Judge Rakoff.

"Or even scurvy," Mr. Naftalis chimed in.

Messrs. Naftalis, Gupta and Brodsky declined to comment. Judge Rakoff also declined to comment.

At one point in the trial, when Judge Rakoff explained to a confused witness that 1786 was the page number in a transcript, and not a year, Mr. Naftalis said, "Even I wasn't born in 1786."

"So you allege," the judge shot back, to laughter.

For Judge Rakoff, a 68-year-old musical theater buff, the bench is often a stage where he tells stories and unleashes punch lines with a throaty laugh.

Mr. Naftalis, 70, is a veteran of the white-collar bar. During one exchange between himself, the judge and a prosecutor, Mr. Naftalis muttered about an "Olsen and Johnson routine," alluding to rowdy comedians famous from the vaudeville era until the 1950s.

After Mr. Naftalis complained that prosecutors had certain evidence delivered to them before the defense received it, Judge Rakoff responded: "You mean to say you don't have FBI agents who can run errands for you?"

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Gary Naftalis

"At one time when I was a youth, or a 'yute,' as someone said in the movies once," said Mr. Naftalis, a Newark, N.J., native, who was a prosecutor in his younger days. The reference was to a courtroom scene in "My Cousin Vinny," in which Joe Pesci's character pronounced "youth" with a heavy New York accent.

Most of the proceedings have been hard-fought arguments over the case, in which Mr. Gupta, the former leader of consulting firm McKinsey & Co., is charged with leaking tips about Goldman and Procter & Gamble Co., where he was also on the board, to former hedge fund manager Raj Rajaratnam.

But levity has come nearly every day, with jurors present and without them. At one point, Mr. Brodsky spelled out the last name of a witness: "M-A-H-A-D-E-V-A."

"The usual!" Judge Rakoff said. "The usual spelling," Mr. Brodsky said.

They have chuckled at some of the big names in the case, including Warren Buffett, whose $5 billion investment in Goldman was the subject of an alleged tip. Mr. Naftalis objected to the description by a witness of Mr. Buffett as the world's most respected investor—the "Babe Ruth" or "Joe DiMaggio" of Wall Street, as the defense lawyer put it.

"I know that your broker disagrees strongly," said the judge. A spokesman for Mr. Buffett didn't respond to a request for comment.

As Mr. Naftalis sought to finish questioning a P&G executive, the lawyer discussed with the judge what questions he could pose to the witness regarding concerns that during the economic downturn consumers would buy generic brand products, such as detergent, instead of the company's brand name Tide, for instance.

Judge Rakoff urged Mr. Naftalis to stay on schedule with his questioning—but not without joking: "Keep in mind that you said a half hour…and time and Tide wait for no man."

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