He didn’t succeed. For anyone sitting in the courtroom during the epic antitrust trial, Judge Jackson’s denunciation of the company last week should come as no surprise. From the outset of the trial in October 1998, the U.S. District Court judge was often perturbed at the software giant–and frequently failed to conceal his scorn. There was the eye rolling at Bill Gates’s evasive videotaped testimony. There were the incredulous head shakes as Microsoft executives tried to disavow incriminating e-mails. When Microsoft lawyers complained about the way Gates’s testimony was being used (piecemeal over many days), the judge said, “I think the problem is with your witness, not with the way in which his testimony is being presented.” During testimony, the judge regularly munched ice cubes.

While the Microsoft affair is undoubtedly the highest-profile case of Jackson’s career, it isn’t the first time the Harvard Law School graduate has made waves. After presiding over the case against former Washington, D.C., mayor Marion Barry, which ended in a meager misdemeanor count of drug possession, he publicly criticized the jury. During the 1987 perjury trial of former White House aide Michael Deaver, Jackson tried to close jury selection to the public, but was overturned. He raised eyebrows by discussing the pending Microsoft case in front of lawyers for both sides. Earlier this year, Sen. Slade Gorton of Washington state called Jackson “a second-or third-rate judge” for “unjustified” attacks against his constituent. And Jackson’s penchant for long breaks and inconsistent sentencing prompted Washingtonian magazine to call him “one of the least respected judges on the federal bench.”

Yet Jackson has been widely praised for his handling of the Microsoft case. A technical neophyte, he quickly learned to throw around such arcane techie terms as “.dll files” and “APIs.” The heavyset jurist also managed to compress an exceedingly complex proceeding into just 76 days by restricting the number of witnesses and limiting their time on the stand. By contrast, the unsuccessful antitrust case against IBM droned on for 13 years. “He’s shown that it’s possible to manage a case of these dimensions in less than a lifetime,” says William Kovacic, a law professor at George Washington University.

If there’s no settlement, Jackson will next decide if Microsoft broke the law–and ultimately, perhaps, what price Microsoft might pay. In the end, this avuncular judge may prove to be Bill Gates’s most formidable foe.