World Economic Forum/Michael Wuertenberg

Rajat Gupta, the former chief executive officer of McKinsey & Co., was sentenced to two years imprisonment for insider trading this afternoon during a hearing presided over by Judge Jed Rakoff at the U.S. Southern District courthouse.

Mr. Gupta, who was convicted in May of using his position on the board of directors at Goldman Sachs to pass privileged information to Galleon Group hedge fund manager Raj Rajaratnam, has sought probation in lieu of imprisonment. The government recommended a jail term of eight to 10 years.

“With today’s sentence, Rajat Gupta now must face the grave consequences of his crime," said U.S. Attorney Preet Bharara in an emailed statement. "His conduct has forever tarnished a once-sterling reputation that took years to cultivate. We hope that others who might consider breaking the securities laws will take heed from this sad occasion and choose not to follow in Mr. Gupta’s footsteps.”

In arguing for a lighter sentence, Mr. Gupta's attorney Gary P. Naftalis  reiterated his client's "extraordinary" philanthropic record, reading from letters written on behalf of the former corporate chieftain, and argued that Mr. Gupta's fall from grace was punishment enough for his crimes.

"He had one of the best reputations on the planet," said Mr. Naftalis at today's hearing, which The Observer attended from an upstairs spillover room at the downtown Manhattan courthouse. "His reputation was a lot more important than any amount of money could be."

Judge Rakoff acknowledged Mr. Gupta's humanitarian record, but said that insider trading was "easy to commit, hard to catch," and that the need for deterrent was strong.

The effect of Mr. Gupta's crime, said Judge Rakoff, was "to place in jeopardy the integrity of the marketplace, one of the greatest assets this country possesses."

Mr. Gupta is generally considered to be the most prominent figure to be convicted during the government's ongoing crackdown on insider trading, which has netted more than 70 convictions or guilty pleas over the last three years. Mr. Rajaratnam, the hedge fund manager at the hub of many of the Justice Department's recent insider trading cases, is currently serving an 11-year prison sentence.

Mr. Gupta was also fined $5 million.

The downgrade didn't prevent Spain's Amancio Ortega, founder of retail giant Inditex, from becoming Europe's richest person, according to the Bloomberg Billionaire Index.

“We have no sense that European partners will follow this tactic of blackmail heard from some quarters and stop funding,” Alex Tsipras, leader of Greece's anti-bailout Syriza party told Bloomberg Television. Rather, Mr. Tsipras thinks that Greece can break the terms of the European rescue agreement signed by a previous Greek government without being forced to exit the eurozone.

"If the Greeks do not meet the commitments they have made, do not meet their financial commitments, do not repay loans, Slovakia will demand that Greece leaves the euro zone," Slovakia Prime Minister Robert Fico said at a news conference today.

Credit Agricole's Grexit contingency plans include walking away from Greek assets, The Wall Street Journal reports.

Germany beat the Netherlands 2-1 on goals by Mario Gomez.

Softballs: Jamie Dimon got in and out of Senate Banking Committee hearings without being pressed too hard on JPMorgan's recent trading losses, and Heidi Moore says it comes down to one chief reason: No amount of regulation can prevent banks from making stupid decisions.

Mr. Dimon's recent troubles may have created space for another Wall Street boss to claim the title of America's Least Hated Banker.

Emerging market: Large institutional investors and the Wall Street firms that bank them are talking about creating an electronic marketplace for corporate bonds, The Journal reports. BlackRock and Goldman Sachs are among firms that have begun building their own platforms.

Lawyer's suit: Former Dewey & Labouef partner Henry Bunsow is suing the law firm, which filed for bankruptcy on May 28, charging that the firm encouraged partners to make capital investments in the firm in what amounted to a pyramid scheme. "Defendants used partner capital investments as a form of revenue to enrich themselves and to hide the dire condition of the firm from the public,” read Mr. Bunsow's complaint.

Tear-jerker:Wily defense counsel Gary P. Naftalis drew tears from client Rajat Gupta, the former McKinsey & Co. founder accused of passing corporate secrets to Galleon Group's Raj Rajaratnam, during closing remarks of the insider-trading trial at the U.S. Southern District courthouse in downtown Manhattan. “Whatever you do here will mark whatever future he [Gupta] has left,” Mr. Naftalis said. “To believe the argument of the defense team, you’d have to believe Mr. Gupta is one of the unluckiest men in the world,” prosecutor Reed Brodsky told the jury.

“We have the spent the last day reviewing what we believe we need to present in the defense case,” Mr. Naftalis wrote. “After substantial reflection and consideration, we have determined that Mr. Gupta will not be a witness on his own behalf in the defense case.”

That news marked a change in course, according to The New York Times, which reports that Mr. Naftalis told the court last week it was "highly likely" that the defense would call Mr. Gupta to the stand. On the other hand, it may simply mark Mr. Naftalis' decision to discard an oft-used red herring.

"If you want your adversary to waste time preparing for a cross-examination, you might make them think that you're going to call the defendant," Columbia law professor John Coffee told us about a week ago, during a call to discuss the challenges of prosecuting white collar crimes. "It he took the stand it would be make-or-break, and I don't see a veteran counsel like Mr. Naftalis going through with it."

With Mr. Gupta off the docket, closing arguments could begin as soon as tomorrow.

[World Economic Forum/Michael Wuertenberg]

Deposits in German banks rose 4.4 percent against the year before, as uh, Greeks, Spanish and Irish wised up.

European takeovers are down 23 percent year-to-date, by the way.

Ben speaks: Federal Reserve Chairman Ben Bernanke said the central bank was watching the European situation closely, but gave no indication that further monetary stimulus was imminent.

The Fed will hold all U.S. banks to the regulatory schema known as Basel III, and The Wall Street Journal is shocked that smaller lenders weren't exempted.

Mr. Bernanke also warned Congress not to ignore the so-called fiscal cliff that arrives when Bush tax cuts expire at the end of 2012. “If you all go on vacation, it’s still going to happen,” he said.

Here all week: The New York Times' Peter Lattman reports on Goldman Sachs CEO Lloyd Blankfein's testimony yesterday in U.S. v. Gupta. “You became the No. 1 person at Goldman Sachs,” [defense counsel Gary P.] Naftalis said. Mr. Blankfein corrected him. “Chairman and chief executive is my official title,” Mr. Blankfein said. He then broke into a smile. “No. 1’s not an official title.” Blankfein will testify today, as the trial drags on.

Shareholders spring: Chesapeake Energy holds its annual shareholder meeting today in Oklahoma City. Could be a good one.

So sorry: Nomura Holdings apologized to shareholders for its involvement in three insider-trading cases.

Oops: Floyd Norris says MF Global was yet another case of accounting practices that "produced profits that vanished before they were actually realized."

After Goldman: Paul Deighton, a Goldman Sachs investment banker for 22 years, is the guy running the show at the London Olympics.

Banker passes: Former Wachovia chief executive officer John Medlin died at 78.

Lloyd Blankfein testifies at the insider trading trial of Rajat Gupta (r.) as Judge Jed Rakoff looks on. (Shirley Shepard/AFP/GettyImages)

For anyone who’d like to see the bank executives who led America into the teeth of the financial crisis strung up by the laces of their Prada wingtips, a trip to the Southern District courthouse in Lower Manhattan may be a deflating experience.

The Observer had come to the federal courthouse seeking succor. Late last month, Reuters laid hands on an internal memo from the Securities and Exchange Commission declaring its investigation into Lehman Brothers was unlikely to lead to criminal charges. In the time it took Dick Fuld to type “the Bros always wins!!” the SEC was feeding reporters the company line: Lehman prosecutions were still a possibility.

That claim became harder to credit this weekend, alas, when SEC enforcement director Robert Khuzami told C-Span cameras that the worst crisis-era bets on souring mortgage bonds were made below the level of the executive suite. (Hmm. Did someone forget to eat his Wheaties?)

U.S. v. Gupta was supposed to be another story. Southern District U.S. Attorney Preet Bharara has been on an insider-trading tear, after all, winning convictions or guilty pleas in 59 of the 66 cases his office has brought since 2009. In the most high-profile case, the government gained an 11-year sentence for Raj Rajaratnam, the billionaire hedge fund manager caught paying corporate insiders to convey privileged information.

Rajat Gupta was among those who supplied Mr. Rajaratnam inside dope, the government said, alleging the former Mc-
Kinsey & Co. chief executive used his standing as a board director at such corporations as Goldman Sachs and Procter & Gamble to pass secrets to Mr. Rajaratnam’s Galleon Group. In one damning-if-true instance, the government says Mr. Gupta telephoned Mr. Rajaratnam minutes after learning that Warren Buffett’s Berkshire Hathaway was primed to invest $5 billion in Goldman Sachs. Galleon bought Goldman stock—and turned a quick million-dollar profit.

But securities law, it turns out, is not the best fuel for populist outrage. We knew that white-collar prosecutions were notoriously hard to win, that wealthy defendants could spend vast sums on defense lawyers, that the complexities of financial cases could wilt the attention of the perkiest juries. It wasn’t until we’d planted ourselves on the hard wooden pews at 500 Pearl Street that we felt the full gravity of the conventional wisdom.

The resource gap between defense and prosecution was clear on the first day of the trial, when four attorneys from Kramer Levin Naftalis & Frankel huddled in the courtroom with an outside jury consultant, even as junior lawyers back at the firm’s Midtown offices poured over a real-time feed of the trial transcript. The prosecution objected. Surely it wasn’t fair for the defense to employ muscle outside the courthouse to research potential jurors’ names? They might as well outsource the voir dire to a team of freelance Facebook trawlers in Bangalore! But Judge Jed Rakoff—the same cranky legalist who’s made a reputation for hard treatment of financial institutions—allowed the outside help.

It got worse. Though the charges against Mr. Gupta are particularly egregious—a board director at Fortune 500 companies stepping out of a confidential meeting to funnel stock tips to a hedge fund manager is about as morally offensive as insider trading can get—the evidence is largely circumstantial. In its case against Mr. Rajaratnam, the government had smoking-hot wiretaps and corroborating witnesses to prove their case. It still took jurors a week to return a guilty verdict.

The evidence in Gupta was flimsier: witness testimony and phone records indicate that Mr. Gupta and Mr. Rajaratnam spoke around 3:55 p.m. on the day Mr. Buffett announced his Goldman stake, for instance, and in a wiretapped call the next day Mr. Rajaratnam told a Galleon trader that he’d received a tip that  “something good might happen to Goldman.” In a wiretapped call a month later, Mr. Rajaratnam told another trader that “I heard yesterday from someone who’s on the board of Goldman Sachs that they’re going to lose $2 a share, the market has them making $2.50.”

It wasn’t hard to connect the dots, but that doesn’t mean a jury will try.

The defendant, meanwhile, had the best lawyers money could buy poking holes in the government’s case. Since Gary P. Naftalis left a post as a Southern District prosecutor more than three decades ago, he’s been tapped by everyone from Kidder Peabody and Salomon Brothers to Michael Eisner and the former-CEOs of Arthur Andersen and WorldCom. The Times has dubbed Mr. Naftalis “Columbo with a law degree” for the lawyer’s disheveled looks and folksy sense of humor. In Judge Rakoff’s courtroom, Mr. Naftalis appeared as if he’d just stepped out of a rainstorm (it wasn’t raining). The Observer wasn’t fooled, of course, but we were a little bit charmed and certainly discouraged.

Mr. Naftalis is the type of lawyer you get when you have millions in the bank and a strong desire to stay out of prison. He’s the kind of lawyer that the prosecutors on the case, Reed Brodsky and Richard Tarlowe, may dream of one day becoming.

Mr. Naftalis’s goal was to blow some smoke, and he proved adept at it.

“If you’re the defense, the normal procedure is to get the jury confused and bored,” John Coffee, a Columbia law professor, told us. “If they’re bored, they miss the smoking gun when it’s produced. If the defense can get the legal issues convoluted, the jury is unlikely to send a man away over issues they can’t understand.”

He added: “I’ve testified as an expert witness in securities cases and looked over and actually seen jurors sleeping.”

“It’s part of the reason that there are so few criminal prosecutions,” said Steve Thel, a professor at Fordham Law. “Prosecutors are reluctant to take on complicated cases.”

Those selected to sit in judgment of the Gupta case included a registered nurse, an elementary school teacher and a freelance beauty consultant. “I am in awe of our jury because they have managed to remain attentive,” Judge Rakoff said last week, urging lawyers on both sides to make things more interesting.

Assistant U.S. Attorney Brodsky started dumbing down the financial lingo with his very first witness, asking Mr. Rajaratnam’s former executive assistant to define a hedge fund. “It’s a place where stocks are traded,” the witness answered. And we thought it was the loose bills our Auntie Vera keeps stashed in a coffee can to pay for gardening supplies! The next day, Assistant US Attorney Tarlowe asked a witness what an index was. “It’s a stock made up of other stocks,” came the reply.

At least the defense left those definitions uncontested. On day three of the trial, the defense unleashed a barrage of objections to Mr. Tarlowe’s examination of the trader who executed Mr. Rajaratnam’s infamous Goldman trade.

“What does it mean to raise $2.5 billion in a common stock offering?” Mr. Tarlowe asked.

“Objection,” offered the defense. Sustained.

“What is your understanding of what it means to raise $2.5 billion in a common stock offering?” Mr. Tarlowe reworded.

“Objection,” said the defense. Sustained.

“Do you know how a stock offering works?” Mr. Tarlowe attempted.

“Yes,” said the witness.

“How do you know?” asked Mr. Tarlowe.

“Objection.”

“Was that objection on foundation or relevance?” Judge Rakoff chimed in. “Foundation and relevance,” Mr. Naftalis quipped, turning to the press gallery, “and whatever else we can think of.”

There were other moments of drama. After one cross-examination, Mr. Naftalis exclaimed “Got him!” loud enough for the jury to hear. On another occasion, the defense counsel made a thumbs-up as he walked away from the witness stand. Mr. Brodsky complained about the grandstanding. Mr. Naftalis complained about Mr. Brodsky’s treatment of a witness. “I think we’re down to a very polite form of name-calling and that’s not what I want to hear from either counsel,” Judge Rakoff scolded, but the defense had gotten the better of the exchange.

Prosecutors don’t generally try cases they can’t win, and the government may have a key element on its side. “Juries pick up signals from the judge,” said Mr. Coffee. “If the judge is leaning one way or another, the jury tends to lean in the same direction.” Judge Rakoff has developed a reputation in recent years as a thorn in the side of financial firms, most recently blocking an SEC settlement with Citigroup and chiding the watchdog for letting the bank off the hook without either a fine or an admission of wrongdoing. “The most disturbing thing about this case is what it says about business ethics,” Mr. Rakoff told the courtroom in the Gupta case. “It’s not a case of one bad apple, but a bushelful.”

Nor would we trivialize the government’s efforts. If Mr. Gupta used his position as a corporate director to feed Galleon Group profitable secrets, Mr. Gupta should go to jail. But we confess to having held out hope, in whatever naïveté, that the government still had bigger fish to fry. After all, Lehman’s bankruptcy examiner Anton R. Valukas reported that Lehman Brothers moved up to $50 billion in bad assets off the firm’s balance sheet in so-called Repo 105 transactions, concealing the bank’s failing state from shareholders and regulators alike. The SEC is pursuing cases against senior officers at Fannie Mae and Freddie Mac, but the claims seem to stop short of criminalizing the mortgage giants’ role in the foreclosure crisis. Indeed, whatever the government’s chances in Gupta—Mr. Coffee handicapped the trial at 60-40 in favor of a conviction—our visit to Judge Rakoff’s courtroom didn’t do much to engender hope of bigger cases.

There’s another challenge to securing convictions in white-collar cases: tangible victims are often lacking. Indeed, it was Mr. Gupta—a silver glint in his combed-back hair, mouth frozen in a dignified grimace—who gave off the air of the wronged party. Behind him sat two benches full of supporters, often including his daughters, who looked just as polished as you would expect from a foursome who holds seven Ivy League degrees. What’s that you say? What about the shareholders in the firms Mr. Gupta allegedly betrayed, or the taxpayers who propped up failing financial institutions?

We suppose those victims were everywhere in the Southern District courthouse, whether they realized it or not.

pclark@observer.com