His lawyer, Mel Honowitz, confirmed the death. Mr. Palladino had been on life support after suffering a head injury Thursday, following an attempted robbery outside his home in San Francisco, where a man jumped out of a car and tried to steal his camera. Images from the camera led to the arrest of two suspects, according to the San Francisco Chronicle.
“If you had known Jack, that’s incredibly fitting,” said Honowitz, noting that Mr. Palladino had apparently solved the circumstances of his own death.
Mr. Palladino worked for more than four decades with his wife, Australian native Sandra Sutherland, forming an elegant investigative power couple that journalists routinely likened to Nick and Nora Charles, the sophisticated sleuths of the Dashiell Hammett mystery novel “The Thin Man” and Hollywood film series.
While Sutherland often went undercover, Mr. Palladino found it rather more difficult to swap identities. Standing 5-foot-10 and weighing 200 pounds, he was balding and bespectacled, fond of Balenciaga ties, silk shirts and red tassel loafers. He investigated murders and drug smuggling but never carried a firearm, explaining that “guns make you lazy, so you don’t look for more creative ways out of a situation.”
Mr. Palladino’s clients ran the gamut from international marijuana traffickers and sexual predators to human rights organizations and Hollywood stars. He worked on the Patty Hearst kidnapping case, investigated the mass suicide at the Peoples Temple’s Jonestown complex in Guyana and helped defend Jeffrey Wigand, the tobacco-industry whistleblower portrayed in Michael Mann’s 1999 movie “The Insider.” Mr. Palladino played himself in a cameo.
He also worked with actors Kevin Costner and Robin Williams; rappers MC Hammer and Snoop Dogg; hip-hop executive Suge Knight and automobile magnate John Z. DeLorean; Hells Angels leader Sonny Barger and Black Panthers co-founder Huey P. Newton; and R&B singer R. Kelly, who was acquitted in a 2008 child pornography trial and faces a new round of child pornography and obstruction charges.
“I am somebody you call in when the house is on fire, not when there’s smoke in the kitchen,” Mr. Palladino told the San Francisco Examiner in 1999. “You ask me to deal with that fire, to save you, to do whatever has to be done to the fire — where did it come from, where is it going, is it ever going to happen again? People call me because they are in a great deal of trouble, and sometimes in a great deal of pain.”
Mr. Palladino was best known for his work with Clinton, which began soon after Gennifer Flowers came forward during the Arkansas governor’s 1992 presidential campaign, alleging they had a 12-year affair. While Clinton would later admit to having had sex with Flowers — an Arkansas state employee and lounge singer — Mr. Palladino worked to undermine her story. In a memo to the campaign, he wrote that it was his mission to impugn her “character and veracity until she is destroyed beyond all recognition.”
To that end, he traveled the country interviewing current and former acquaintances of Flowers, some of whom called her to inquire about the “very strange” man asking whether she was sexually active or “the type to commit suicide.” At the time, senior Clinton aide Betsey Wright defended the campaign’s actions as “self-defense,” telling The Washington Post that tabloids and talk shows had offered more than $100,000 to women who shared embarrassing stories about the candidate.
Mr. Palladino, she said, was being used to address “bimbo eruptions,” and had been successful at keeping a number of the alleged scandals out of print.
Larry Sabato, a University of Virginia political scientist, later told the New Yorker that Mr. Palladino oversaw “a very aggressive campaign to suppress information.” He faced persistent criticism from figures such as former Clinton adviser Dick Morris, who called Mr. Palladino a member of the president’s “secret police,” and New York Times columnist William Safire, who labeled Mr. Palladino one of “the lowlifes hired by Clinton lawyers.”
Mr. Palladino said that he was simply pursuing the truth (“I am a heat-seeking missile that goes after a lie”), although he acknowledged that he sometimes lied about his identity in the course of an investigation. His tactics reportedly included making surreptitious recordings, using attractive women to elicit information from men, and alternately charming and intimidating journalists by revealing that he knew their past addresses, prior jobs and former romantic partners.
“I go right to the boundaries of the envelope,” he told the Examiner. “Nothing could be alleged as illegal or improper or unethical.”
Mr. Palladino faced renewed criticism after the New Yorker reported that he had worked for Weinstein, the film producer and Miramax co-founder who was convicted last year on sexual assault charges. According to a 2017 report by journalist Ronan Farrow, Mr. Palladino and another investigator had produced dossiers on Weinstein’s accusers, as well as on journalists involved in the coverage, “which included information that could be used to undermine their credibility.”
“The credibility of witnesses and the verifiability of allegations are always at issue in litigation,” Mr. Palladino said in a statement at the time. “That is not only our firm’s particular expertise as investigators, but our legal and ethical due process obligation in the representation of our clients.”
John Arthur Palladino was born in Boston on July 9, 1944. His father was a pipe fitter, and Mr. Palladino said he grew up in a tough neighborhood where kids could get beaten for carrying books. He graduated from Boston Latin, a selective public school, and enrolled at Cornell University, where he married a fellow student at age 19. They divorced a few years later, and he received a bachelor’s degree in English in 1966.
Mr. Palladino reportedly won a Ford Foundation fellowship to study for a master’s degree at the University of California at Berkeley. University records indicate he received a bachelor’s degree from the school in 1968, followed by a law degree in 1975.
By then he was determined to work as a private investigator, drawn to the field by casework that included going undercover in 1971 to investigate corruption and brutality at the Nassau County jail on Long Island. Pretending to be a fur thief, he helped gather evidence leading to the indictment of 24 prison guards. In a grand jury hearing room he met Sutherland, who had been working independently at the jail, also undercover.
Together they worked in the San Francisco office of investigator Hal Lipset, a master of electronic surveillance, before getting married in 1977 and opening their own investigative agency, Palladino & Sutherland. Within a decade they had moved into a two-unit Victorian mansion in the Haight-Ashbury district, and were living in one side of the house and working in the other.
“I’m not a self-effacing individual,” Mr. Palladino told the Examiner. “I am a driven, arrogant person who holds himself and everyone around him to incredibly high standards. I’m very difficult in private life. I don’t live for anything but this.”
In addition to his wife, survivors include three stepchildren and a brother.
Mr. Palladino raised his firm’s profile with a slew of major cases in the 1980s, including helping unveil a smear campaign organized by American Express, which aimed to tarnish the reputation of rival banker Edmond J. Safra. By the time the Clinton campaign hired him, he was working for $2,000 a day.
In 1998, he spent weeks hiding out from lawyers for Paula Jones, who had sued Clinton for sexual harassment and were trying to serve Mr. Palladino with a subpoena in an effort to learn more about the president’s past. Mr. Palladino boasted in an interview with the New Yorker that as an investigator who had to serve people with subpoenas, he certainly knew “how not to be served.”
He was similarly cheeky when Jane Mayer, a writer for the magazine, asked what he thought of the allegations that Clinton had had a sexual relationship with White House aide Monica Lewinsky — a scandal that led to the president’s impeachment.
“Well,” he said, “in a joking way, I have to say that either the president should have had the judgment never to get involved with someone like that — or else he should have kept me on permanent retainer.”