‘He investigated his own murder’: Famed S.F. detective Jack Palladino is dead

In his 1970s aviator sunglasses and a bushy mustache, Jack Palladino looked like a Soviet-era spy or a double agent. He wasn’t, but he was close. Palladino was a private eye — a snoop who could dig up a crucial witness or piece of evidence or follow a money trail to clear or convict a defendant at trial.

Palladino did not carry a gun, which he often said would make his job too easy. His weapon of choice was a camera with a long lens, strapped around his neck, and that may have been what got him killed.

On Thursday afternoon, Palladino was in front of the Haight-Ashbury home/office he shared with his wife and business partner, Sandra Sutherland, when he was allegedly assaulted by two men in a gold Acura, who reached out from the car to steal his camera. Palladino held on in a tug-of-war, according to witnesses, and was dragged. During the struggle he fell and hit his head on the pavement.

Rushed to UCSF, he never regained consciousness and was taken off life support on Sunday. He died shortly after noon Monday, according to his attorney, Mel Honowitz, of San Francisco. Palladino was 76. Cause of death was traumatic brain injury, Sutherland told the Chronicle.

Palladino’s camera held images that led to the arrest of two suspects.

“He investigated his own murder,” said Honowitz. “Those of us who knew Jack are mourning his death but chuckling that it is a fitting way for him to go.”

He was, perhaps, the highest profile investigator in San Francisco, over the last 15 years of a career that lasted 50 years.

“He was daunting and scrupulous in his profession,” said Honowitz, a retired litigator. “When the game was afoot, Jack led with intellect, experience and passion for the truth. I cannot think of a stronger advocate for freedom of speech and freedom of the press.”

Though Palladino was a lawyer, he never practiced beyond a clerkship with the famed Melvin Belli. He was drawn to private investigator work for the action. Palladino began his career in 1972 working for Hal Lipset, the dean of San Francisco investigators. At the time, TV-show characters like Frank Cannon and Joe Mannix made the private detective trade glamorous and heroic.

During this golden age, a group of investigators led by Lipset used to take over the long bar at John’s Grill, the hangout of the fictional Sam Spade, for a cocktail hour that would sometimes bleed into closing hour. Palladino wasn’t always there, but when he was, you knew it.

“He was exceptional in the investigation industry, very high-profile,” said Jack “The Rope” Immendorf, who may now be the last of the old-time private detectives. “Investigators are not trained at school. It takes a certain type of individual, someone who can communicate with people at all levels and know the streets. Jack had all of these qualities and more.”

Trained in the law at UC Berkeley’s Boalt Hall, Palladino could immediately understand a case and outsmart whoever he was working against.

Usually hired by attorneys to find or disprove information and help build a court case, Palladino worked on the kidnapping of Patty Hearst and the Peoples Temple mass suicides at Jonestown. Hells Angels leader Sonny Barger and Black Panthers co-founder Huey P. Newton were clients. Palladino also worked on behalf of John DeLorean, the sports car inventor who was charged with trafficking cocaine to support his company.

“You never know what the next phone call is going to be about,” said Immendorf. The most high-profile call that Palladino got was from the campaign of Bill Clinton during the politician’s first presidential run in 1992. His campaign hired Palladino in 1992 to help quell rumors of his extramarital affairs.

“All we are trying to do is defend against the war of lies directed at Bill Clinton,” Palladino said at the time. “This is the dirtiest campaign I have ever seen.”

Palladino’s work on behalf of the Clinton campaign later brought him into the scrutiny of investigators. Palladino was subpoenaed during the Kenneth Starr investigation of Whitewater and the Monica Lewinsky and Linda Tripp revelations, but never had to appear.

Always discreet, Palladino never said exactly what he did for any of his clients, including former Mayor Willie Brown, who paid him $15,000 during his mayoral campaign in 2000. This was probably in the subcategory known as “opposition research,” Palladino said. “When people are running for office you want to know everything, good and bad.”

Palladino was physically imposing but not an athlete. “He described himself as coming from Sicilian fishing stock,” said Honowitz, who only once saw Palladino display exertion while bounding up stairs to pound on the door of a witness he’d located in Cairo.

His usual style was to invite a witness to lunch or dinner and charm them out of whatever he needed, often without the person ever knowing what was being divulged. He was so likable that witnesses were naturally prone to helping him even if he was working the other side.

San Francisco attorney Marcus Topel, who worked with Palladino on numerous cases, once told The Chronicle that Palladino was the best in the business at coaxing crucial information from sources.

“He’s an extremely talented and creative private investigator who is relatively fearless about where he goes,” Topel said. “Over the years, he has helped me break cases wide open. ... He’s been very successful, and he’s made a lot of enemies and had a controversial life.”

In 2017, he was in the employ of convicted Hollywood sexual predator Harvey Weinstein, looking for holes in the credibility of some of Weinstein’s accusers. Asked for a comment by Chronicle columnists Phil Matier and Andy Ross, Palladino sent a statement:

“The credibility of witnesses and the verifiability of allegations are always at issue in litigation. 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.”

Palladino got tremendous flak for representing Clinton and less flak for representing Weinstein and the Chicago musician R. Kelly, who allegedly had sex with a minor. But criticism was part of the job, and also good for business.

“Jack was an absolute believer in due process,” Honowitz said. “Everybody should have a full and fair defense, and he would have been the first to tell you that even the people who murdered him should have appropriate due process.”

He also worked the other side, helping a 14-year-old boy toward a multimillion-dollar settlement in a civil suit against Michael Jackson for alleged molestation. In 1993, Palladino investigated an extortion attempt by an HIV patient at Pacific Presbyterian Medical Center who allegedly had threatened to infect other patients with the virus.

One of his higher profile cases was the “Tobacco Wars,” about the manipulation of nicotine content by manufacturers that resulted in congressional hearings. It also resulted in a movie called “The Insider,” in which Russell Crowe portrayed whistle-blower Jeffrey Wigand, and Palladino portrayed himself.

John Arthur Palladino was born July 9, 1944, in Boston, a plumber’s son. He stood out in school and gained admission to the prestigious public Boston Latin high school and a scholarship to Cornell University, where he worked in a physics lab. He came west in 1967 to pursue graduate study in political science with an emphasis on Chinese studies and managed to transfer to what is now known as Berkeley Law.

After a brief stint launching his polling and research service, he hired on with Lipset. One of his first investigations was also his most dangerous when he went undercover at Nassau County jail on Long Island to investigate living conditions and criminal activity by the guards and prison trustees. As part of the same investigation, Sutherland was also undercover in the women’s section, and they met while tying up the investigation.

“He liked to joke that he met his wife in prison,” Honowitz said. But it wasn’t entirely true. According to Sutherland, they met in a 727 jet while flying from San Francisco to New York to give testimony, which resulted in the indictment of 22 guards and two Mafiosi, she said.

She was from Canberra, Australia, and was coming off a divorce. They were both working for Lipset, Sutherland as a salaried investigator and Palladino on a freelance basis.

“I was sick of dating, and thought ‘Oh, Good old Jack, we can go out and at least talk shop.’”

As Sutherland tells it, they were both so busy working on cases, that the honeymoon to Hawaii they had booked came around before they had scheduled the wedding. So they took the honeymoon and were married four days into it, on Jan. 27, 1977.

A few months later, Sutherland left Lipset and they split off to form Palladino & Sutherland.

“As partners, they complemented each other,” said Immendorf. “Female investigators are sometimes quite successful at eliciting information from reluctant witnesses.”

Palladino also often partnered on investigations with his younger brother Paul, also a private investigator, in Southern California.

Sutherland retired in the 1990s, and in 2020, Palladino reportedly said he was looking forward to semi-retirement, which is as far as he would go. He wanted to spend more time on his photography, shooting portraits of people in the neighborhood, and all over the world. He had visited Cuba, Spain and Morocco. Palladino and Sutherland have been just about everywhere. Even if waiting for a flight, he kept himself busy.

Palladino & Sutherland operated out of a big yellow corner Victorian at 1482 Page St., a block from the panhandle of Golden Gate Park. It was there that he met his final case.

“The world is a worse place without him,” said Honowitz. “Jack was a giant and a great humanitarian.”

Sam Whiting is a San Francisco Chronicle staff writer. Email: swhiting@sfchronicle.com Twitter: @samwhitingsf