Jack Palladino, a hard-nosed private detective known for taking on high-profile clients from Bill Clinton to Courtney Love, is in critical condition and not expected to survive after being injured Thursday afternoon during a robbery outside his home in the Haight.

Palladino, 76, an avid photographer, had just stepped outside his home near Masonic Avenue and Page Street to test out a new camera when someone tried the take it from him, according to police and his family. Palladino was pulled to the pavement and seriously injured.

He remained on life-support as of Friday night, his family said.

Palladino was known in his career for representing celebrities and sometimes dangerous clients including the Hells Angels.

Born to a working class family in Boston, Palladino moved to the Bay Area to attend UC Berkeley before founding a detective agency in the 1970s with his wife, Sandra Sutherland. His early cases included work on the Patty Hearst kidnapping and interviewing survivors of the Jonestown Massacre.

He would later help defend the auto magnate John DeLorean on drug charges before being hired to discredit sexual misconduct allegations against Clinton in the 1990s and, more recently, similar allegations against the movie mogul Harvey Weinstein in 2017.

In 1999 Jack Palladino told The Examiner “I am a driven, arrogant person who holds himself and everyone around him to incredibly high standards.” (SF Examiner file photo)

In a profile on Palladino from 1999, the San Francisco Examiner described him as having “built a reputation for aggressive investigations, an in-your-face style and the ability to neutralize adverse witnesses and spin hostile media.”

“I’m not a self-effacing individual,” Palladino told the Examiner at the time. “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.”

Palladino cultivated a persona as a brash private detective who wore flashy suits, his stepson Nick Chapman told the Examiner on Friday.

“He was a somewhat flamboyant character at times and could be very aggressive in defense of his clients,” Chapman said.

But Palladino was also a “real human” who had just decided to retire at the beginning of the year, was reading short stories and had taken up cooking.

“The stuff I read mostly doesn’t capture the man I grew up with and who I worked for,” said Chapman, who worked under Palladino as a private detective.

“He was very passionate about justice, about democracy, about the First Amendment, about people being entitled to the best defense that they could get,” Chapman said. “And he was not blind to the limitations of our justice system.”

Police have not announced an arrest in the case. The investigation remains open.

mbarba@sfexaminer.com

Bay Area NewsCrimesan francisco news