WASHINGTON — Thomas Penfield Jackson, who as a federal judge in Washington presided over a historic Microsoft antitrust case and the drug possession trial of former Mayor Marion Barry, has died.

Jackson died at his home in Compton, Md., his wife Patricia told The Associated Press on Sunday. He was 76 and had cancer.

Jackson, who retired from the bench in 2004, handled a variety of cases in more than two decades as judge. He sent Barry to prison for cocaine possession, conducted the perjury trial of former White House aide Michael Deaver, and ordered then-Sen. Bob Packwood to turn over his diaries to a committee investigating sexual harassment charges.

In 2000, ruling in a closely watched antitrust lawsuit brought by the government against Microsoft, Jackson ordered the software giant to be split in two after concluding the company had stifled competition and used illegal methods to protect its monopoly in computer operating systems. The decision rocked the software industry, and in interviews with the news media that were published after the ruling, Jackson was quoted as comparing Microsoft founder Bill Gates to Napoleon and likening the company to a drug-dealing street gang.

"I think he has a Napoleonic concept of himself and his company, an arrogance that derives from power and unalloyed success, with no leavening hard experience, no reverses," Jackson said in one interview.

An appeals court the following year unanimously reversed the breakup order – though it did agree that Microsoft had acted as an illegal software monopoly – saying Jackson had engaged in "serious judicial misconduct" with his derogatory out-of-court comments about the company. The court appointed a different judge to determine a new punishment. The company eventually negotiated a settlement.

Another high-profile case involved a North Carolina tobacco farmer who in 2003 drove his tractor into a pond on the National Mall, creating a lengthy standoff with the police and threatening to set off bombs. Jackson initially sentenced Dwight Watson to six years in prison, saying the city had regarded him as a "one-man weapon of mass destruction," but later sharply reduced the punishment following a U.S. Supreme Court ruling involving sentencing guidelines.

In 2004, he angered media advocates with his decision to hold five reporters in contempt and fine them $500 a day for refusing to identify their sources about nuclear scientist Wen Ho Lee.

Jackson also presided over the 1990 drug trial of Marion Barry, the District of Columbia mayor caught in an FBI sting smoking crack-cocaine in a hotel room. The judge's original six-month sentence was thrown out after an appeals court said he didn't adequately explain how he applied federal sentencing guidelines.

Jackson re-sentenced him to a six-month term, despite challenges from Barry who said the judge had shown bias by telling a Harvard University audience that he was convinced Barry was guilty of perjury and other crimes but that some jurors would not have voted to convict him on most of the charges under any circumstances. The jury had convicted Barry of drug possession but deadlocked on other charges.

The appeals court refused to let Barry delay serving his sentence.

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