By LARRY NEUMEISTER
Associated Press

NEW YORK — A hedge fund founder once recognized as one of the country's richest citizens would serve the longest sentence in history for an insider trading conviction if a federal judge grants the government's request to send Raj Rajaratnam to prison for two decades.

His sentencing was scheduled for Thursday in Manhattan.

Prosecutors are asking U.S. District Judge Richard J. Holwell to send the 54-year-old, one-time billionaire to prison for at least 191/2 years for his May conviction on securities fraud charges. They say federal sentencing guidelines call for a sentence up to 241/2 years.

The prosecution has placed Rajaratnam's profits from illegal trades between $70 million and $75 million, saying he moved so much money around within his multibillion-dollar funds that the movement of price in individual stocks could be traced to his trading whims.

Lawyers for the Sri Lanka native argue that his sentence should be much lower - 61/2 to nine years - for what they say were illegal profits of about $7 million, when the trades at his Galleon Group of hedge funds are disregarded.

The defense also has asked for leniency partly based on his "failing health" and his "unique constellation of ailments." They say a lengthy prison term will amount to a death sentence.

The sentencing culminates a series of convictions and sentencings that followed the October 2009 announcement of the arrest of Rajaratnam in what prosecutors labeled the biggest hedge fund insider trading case in U.S. history.

In all, more than two dozen people were arrested. All were convicted, with the sentences ranging from a few months to 10 years. Since the first arrests, U.S. Attorney Preet Bharara has widened the probe. A year ago, he said insider trading is "rampant and may even be on the rise."

Using information gleaned from the many cooperators in the Rajaratnam case, prosecutors have focused lately on consultants who are paid to arrange conversations between employees of public companies and hedge fund managers.

Too often, prosecutors say, they have found a nest for insider trading rather than for the discussion of legitimate research.

In their presentence submissions, prosecutors say Rajaratnam lacks remorse, even after a trial that featured the playing of dozens of taped conversations in which he was heard discussing financial news events that were not yet publicly known.

"Rajaratnam has neither acknowledged responsibility for his crimes nor remained silent. Instead, Rajaratnam's post-conviction statements show that he remains defiant that he never committed insider trading and, incredibly, he maintains that the line between legal and illegal conduct was not always clear to him," prosecutors wrote.

They quoted from a report that is not public that he told the Probation Department: "In my own mind, the line between permissible 'detective work' and impermissible insider trading was not always clear, especially with regard to companies broadly covered by the news media as to which there was a wealth of publicly available information, including frequent leaks, rumors and speculation about corporate transactions and other important developments."

The prosecutors wrote that Rajaratnam's comments "do not reflect the proper respect for the jury's verdict, the evidence in the trial record or the laws against insider trading."

Prosecutors also have asked the judge to force Rajaratnam to reveal his medical issues since he is relying on them in his plea for leniency. The judge has not yet ruled on the request. And, in a filing Wednesday, they asked the judge to revoke Rajaratnam's $100 million bail and force him to report to prison within three weeks. He currently is confined to his Manhattan apartment.

In their written submissions, defense lawyers said Rajaratnam should receive leniency with a sentence substantially below the guidelines range because of his failing health and his extensive community service.

The sentencing comes as the nearly month-old Occupy Wall Street protests march on, sending daily messages opposing Wall Street greed and corporate excess.

Filmmaker Danny Schechter, who handed out leaflets at the protests Wednesday calling Wall Street a "crime scene," said the prosecution and sentencing of Rajaratnam might miss the point.