In a career that spanned nearly 50 years, Palladino became known for taking on high-profile and controversial cases. The
San Francisco Examiner noted in 1999 that he had "built a reputation for aggressive investigations, an in-your-face style and the ability to neutralize adverse witnesses and spin hostile media." With Sutherland, he investigated fraud, personal injury, medical malpractice and murder cases. The Clinton election committee reportedly paid Palladino more than $100,000 over several years to investigate two dozen women in a damage control inquiry.
Michael Isikoff claimed the Clinton campaign used deception regarding the payments. He said the payouts came from campaign funds, but were listed as legal fees paid to a Denver law firm rather than payments to Palladino. He further claimed that Clinton's chief of staff
Betsey Wright later told him the funds were for "controlling bimbo eruptions". Palladino was also employed by singer
Courtney Love to talk to journalists investigating whether she was involved in the 1994 death of her husband, singer
Kurt Cobain. Palladino insisted he was never involved in "fear and intimidation" in his investigations and production of dossiers on such journalists. When former tobacco executive
Jeffrey Wigand began cooperating with
60 Minutes on insider revelations of tobacco company manipulations designed to increase smoker addiction, the industry launched a million dollar public relations campaign to discredit him. Palladino engaged in a counter-investigation that turned the spotlight onto this smear campaign and preserved Wigand's credibility as an expert witness in a lawsuit that subsequently resulted in a more than two hundred billion dollar settlement, in the first successful litigation against Big Tobacco. and in the 1999
Michael Mann film
The Insider. In that movie, Palladino appeared as himself, and his partner, Sandra Sutherland, was played by actress Megan Odebash. In 2002, singer, songwriter, and record producer
R. Kelly was charged with videotaping himself having sex with an underage teenage girl. An investigation by Palladino that lasted six years culminated in Palladino's testimony at trial challenging the principal prosecution witness, and the acquittal of Kelly in less than a day. In April 2009, Australian businessman
Peter Holmes à Court admitted in the
Supreme Court of New South Wales that the Hollywood actor
Russell Crowe had hired Palladino & Sutherland to investigate opposition to the planned takeover of the
South Sydney Rabbitohs. Crowe had first gotten to know Palladino and his Australian wife and partner, Sandra Sutherland, when all three worked on the film
The Insider.
Ronan Farrow reported in November 2017 that
Harvey Weinstein had, through the lawyer
David Boies, employed the private intelligence agencies
Kroll Inc.,
Black Cube and private investigator Jack Palladino to spy on and influence Weinstein's
alleged victims as well as reporters who were investigating Weinstein, in order to prevent his conduct from becoming public. Other notable clients included
Don Johnson,
Kevin Costner,
Robin Williams,
Huey P. Newton, the
Hells Angels and
Snoop Dogg. ==Personal life==