Anthony Pellicano handled some sticky situations during his days as a private investigator for some of the biggest names in Hollywood, the AP reported.
He helped Michael Jackson fend off child molestation allegations and found the remains of Elizabeth Taylor's third husband after they were stolen from a cemetery.
One of his toughest challenges, however, has been acting as his own lawyer in his federal wiretapping trial that could go to the jury in the next few days.
Though he built his reputation as a tough-talking, bare-knuckled gumshoe, Pellicano mostly left his aggressive demeanor outside the courtroom and chose to preserve his loyalty to his famous clients rather than reveal their secrets as part of his defense.
He called only one witness during the two-month trial and rarely raised objections. He also decided against taking the witness stand to defend himself, even though prosecutors played a number of profanity-laced audio tapes in which he reassured clients that he would make their problems go away.
His "presumption was that those conversations would never be made available to anybody," Pellicano told jurors with little emotion during a 10-minute opening statement in which he failed to declare his innocence.
"I don't think he's been very effective in court," said Laurie Levenson, a Loyola Law School professor and former federal prosecutor. "He looks like a defendant who doesn't have much to work with."
Pellicano, 64, is accused of running a criminal enterprise that wiretapped the phones of stars such as Sylvester Stallone, and bribed police officers and telephone workers to run the names of celebrities such as Garry Shandling and Kevin Nealon through protected government databases.
He and four co-defendants have pleaded not guilty to a variety of charges.
Pellicano charged clients a minimum of $25,000 and once boasted in a GQ magazine article, "I can shred your face with a knife."
U.S. District Judge Dale Fischer called it a "bad idea" when Pellicano said before trial that he was broke and wanted to represent himself to prevent his lawyers from having to work for free.
He stumbled at the start, finding it difficult to correctly phrase questions and refer to himself as "Mr. Pellicano," as court procedure requires for someone acting as their own lawyer.
Rather than wear a suit, he appeared every day in a prison-issued green jacket, gray shirt and green pants.
He listened attentively to testimony, often leaning back in his chair and staring stone-faced at witnesses, but had no questions for Chris Rock and one-time power agent Michael Ovitz after they testified about using his services. He also passed up the chance to cross-examine Shandling.
Pellicano saved most of his vitriol for associates who cooperated with prosecutors - "rats" as he has called people who betrayed his trust.
His targets included Sandra Will Carradine, the ex-wife of actor Keith Carradine. She had an affair with Pellicano several years ago and later pleaded guilty to perjury in the case.
During her testimony, Pellicano asked why she had lied about her dealings with him.
She said she was protecting him.
"Did he ever tell you to lie for him?" Pellicano asked, referring to himself in the third person.
"No," she replied.
Pellicano also faced off against former reporter Anita Busch, who found a dead fish and a sign that read "stop" on her car in June 2002. Authorities believe Pellicano was behind the threat.
Busch trembled and cried as prosecutors questioned her about the incident. Pellicano rattled her further when he asked about an apparent attempt by someone to run her down outside her apartment.
"You considered this to be a threat?" Pellicano asked.
"Yes," Busch replied, saying she was so afraid that she stopped writing newspaper articles.
"I thought (the threat) meant not to talk to law enforcement," she said. "If I did, it meant I would be killed."
"But you continued to talk to law enforcement, right?" Pellicano pressed.
"Yes, eventually," Busch said.
Pellicano also played tough with shifty witnesses, often reminding them to "just answer yes or no" or "that's not what I asked." He managed to score some points, getting a former telephone supervisor to tell jurors she never checked to see if a wiretap found on Busch's phone was traced back to Pellicano's office.
In addition, he raised doubts about the government's intention in raiding his office when lead FBI agent Stanley Ornellas testified that authorities didn't find evidence of wiretapping during the initial search.
Despite those efforts, Pellicano was mostly unable to counter much of the prosecution's case.
"The skills and techniques that accompany a successful private investigator, unfortunately are not the same skills that make you a good trial lawyer," said attorney Steve Gruel, who previously represented Pellicano.