The Final Kiss Off from Hollywood’s Secret Keeper

Anthony Pellicano
Private investigator Anthony Pellicano. Photo: Michael Montfort/Getty Images
Eriq Gardner
July 24, 2022

This past week, I slogged through a book that features a rather peculiar perspective. This novel tells a tale of two best friends from a rough Italian neighborhood in Chicago—one who grows up to be a private investigator for the mafia, the other who becomes an F.B.I. agent. The premise is promising, but what’s most remarkable is the author’s clear affection for the fictional gangsters, and even for mob justice. What kept me reading to the end was the identity of the author, Anthony Pellicano, and the publisher’s word that this was “his first work of not-so-fictional fiction.”

Pellicano, of course, is one of the most notorious figures in Hollywood history—a former private investigator who once helped half the town spy on the other. A-list clients like Tom Cruise, Michael Jackson, Michael Ovitz, Brad Grey, Chris Rock, and on and on, used his services. Then, one day in 2002, a nosy Los Angeles Times reporter found a dead fish, a rose, and a “stop” sign on her car’s windshield. The F.B.I. began investigating Pellicano, and a whole world of secrets began spilling out into view.

The ensuing revelations (and a dozen lawsuits) ripped the band-aids off of many of the town’s recently resolved disputes. Many of Pellicano’s victims (Sylvester Stallone, Garry Shandling, Keith Carradine, etc.) learned they had been secretly wiretapped or hacked in the midst of divorces, business quarrels, paternity demands, and so forth. When Pellicano went to trial in 2008, convicted of charges including racketeering and wire fraud, simply everyone in Hollywood was watching. I vividly remember the hushed dread from many of the town’s lawyers as well as the true emotional pain from Pellicano’s traumatized victims. Learning about Pellicano at the outset of my career in entertainment journalism was like being handed a map of the relationships—good and sore—in this industry.

Pellicano got out of prison in 2019 and, now 78, he remains a subject of intense fascination. He inspired the Showtime series, Ray Donovan. I even hear The New York Times has been conducting interviews for a future episode on Pellicano as part of its FX docu-series that brought the Britney Spears conservatorship to mainstream attention last year.

With such interest in the guy, it’s amazing that the release of Pellicano’s book in April received absolutely no attention. I mean this literally. Scouring social media, I couldn’t find a single mention of The Neighborhood, nor the audio version that he personally narrates. And how did I come to discover this work of not-so-fictional fiction? Through Pellicano’s Chapter 7 bankruptcy filing, which also went completely undetected. 

What drove Pellicano into personal bankruptcy at the beginning of this year—on $10 million of debt, and royalties from an unreleased book listed as an asset—is a remarkable story in itself. 

It starts with one of Pellicano’s more obscure misdeeds. At the turn of the century, a socialite named Jacqueline Colburn hired Pellicano to investigate her husband, Richard Colburn, a billionaire philanthropist on the verge of a divorce. Pellicano tapped the telephone lines of the Beverly Hills residence where the couple lived. That meant that Pellicano was secretly listening not just to Richard’s calls, but also his children from a previous marriage. 

In 2007, after Pellicano’s other crimes received press attention, Richard, his two kids, and a former assistant sued the ex-wife and her suddenly-embattled investigator for wiretapping. The case would go to trial five years later while Pellicano was in prison. Although Pellicano’s exploits naturally prompted many civil suits (there was even a class action filed and settled against AT&T’s Pacific Bell over his rampant intrusions), all of those other cases never ended up before a jury. The Colburn case did, even if Pellicano didn’t show up. He was served papers in prison and gave a deposition but chose to not mount any defense and lost by default. In Oct. 2012, after a nine-day trial, a Los Angeles jury returned a $3.895 million verdict. The case earned Lawrence Segal, the attorney representing the family, the cover of Los Angeles Lawyer magazine under the coverline, “Who’s Listening,” but the verdict was hardly rewarding financially. Pellicano, allegedly, was broke.

For nearly a decade, Segal did little to pursue the judgment. He tells me he believed that some powerful Hollywood figures have been paying Pellicano under the table to stay silent about their own misdeeds. (Segal isn’t alone in suspecting this.) Nevertheless, Segal elected not to look into what Pellicano might have been stashing in bank accounts. Sometime after Pellicano was released from prison, however, word spread that he had set up a consultancy. In January 2021, Variety published a story headlined, “Anthony Pellicano Is Back in Business and Working for Joel Silver.”

Segal saw the news, and after talking it over with his clients, hired his own private investigator to look into Pellicano’s financial situation. In short, it was Spy vs. Spy. Three JP Morgan Chase accounts for Pellicano turned up. The attorney obtained a writ of execution and had the Los Angeles County Sheriff’s Office seize the funds. According to Segal, Pellicano quickly called him up for details about what was happening. Soon thereafter, Pellicano claimed the money in his bank accounts was exempted from seizure. 

In January, both sides were scheduled to appear in a Los Angeles court to argue over the fate of the seized funds when Pellicano suddenly declared bankruptcy. The Colburn clan, viewing this as an obvious effort to discharge the old legal debt, is contesting. In court papers filed this past week, they say it’s too late for Pellicano to fight allegations of illegal wiretapping, and that the bankruptcy code doesn’t allow debtors to escape the consequences of intentional torts. A bankruptcy court hearing on the matter is scheduled for late August.

Meanwhile, it appears that Pellicano Negotiations, his consultancy and mediation firm, is doing okay. In his Chapter 7 filing, Pellicano states that he is taking in $8,333 in monthly income from his new business. I’ve also spoken to lawyers in the industry who tell me that Pellicano has been pitching his services widely—including, quite brazenly, to old foes. I hear he recently helped two Hollywood bigwigs (whose names I’ll withhold because I haven’t been able to confirm this) settle a feud over a loan.

As for that book, it’s pretty shocking no one noticed its release. After all, over the years, Pellicano has inspired an almost Epstein-like fervor of conspiratorial thinking about who he might be protecting. Those conspiracists have no doubt been encouraged by Pellicano’s own words hinting at having the goods on some famous individuals. In one jailhouse interview, for example, Pellicano said, “I believe rats, informants and others of that ilk are worse than child molesters… I could have ruined many careers and lives… but I would have dishonored myself by doing so.” In that same interview, Pellicano also said, “If you tried to connect me to organized crime, you probably could get close—but no cigar.”

There are still many mysteries about Pellicano’s origin story, which is why The Neighborhood, even if dressed as fiction, might have an audience. In the novel, the main character, Vincent, gets close to local mobsters to obtain a private investigator license. He does work for them, tracking down those in debt. Vincent comes to find he’s good at this type of work—and while initially of the mind that he wishes to remain independent, Vincent is given favor after favor and realizes he can’t resist the temptation to be aligned with organized crime. Meanwhile, Paulie, the other main character, is unceasingly mocked for becoming an F.B.I. agent. At its best, this might have been another Donnie Brasco or The Departed, but it’s hard to see a studio adapting this. That might be a relief to some powerful and famous individuals who have crossed paths with Pellicano. On the other hand, I’m reliably told he’s currently shopping a sequel to publishers.