It was a Thursday around lunchtime in the half-full Rome foreign-press-club bar, barely 50 yards from the Trevi Fountain, and John Phillips was mulling his many troubles, never quite making eye contact, preferring to study the remnants of a bucatini all’Amatriciana. Business was tough, money was tight, and there was that recent small bother involving the United Nations, which was suing him for more than he was worth on several counts of criminal defamation. But he wasn’t really thinking about any of that now.

Instead Phillips was thinking about the slow, sad demise of his beloved profession—along with many of its practitioners. He closed his eyes in thought, recalling a former Rome correspondent for The Daily Telegraph and The Sun. “Very funny man, did very well,” he said wistfully. “But in the end, the booze killed him.”

He scrunched up his face as he tried to conjure his old friend. “It was thrombosis,” he said with uncertainty. He drooped his head into his hands, apparently bored with his own deliberation, his train of thought trailing. Perhaps nearing extinction himself, he had the look of a weather-beaten rhinoceros, his face deeply lined and furrowed. A thinning lock of hair protruded from his forehead.

And then he had it!

“Cirrhosis.” That’s what had killed The Sun’s man.

Peals of laughter erupted from the press-club veterans at the next table. The club, officially the Associazione della Stampa Estera, was where the trouble with the U.N. had begun, and Phillips missed the buccaneering spirit of its halcyon days. In the past, the club had been a debauched redoubt for the daring—a place of Vatican intrigue, exorbitant expense accounts, spirited visits by Gore Vidal, and newspapers bankrolled by the C.I.A.—but it had since deteriorated into a kind of co-working space, featuring ergonomic swivel chairs, stale, smokeless air, and a bar that shut at 4:00 p.m. sharp.

Phillips in a café next to Rome’s Foreign Press Club.

“It’s become a tame place,” Phillips reflected. “The old place was more of a club. This—this is more of a press center.

Excusing himself, Phillips went upstairs to his tiny desk to work on his equally tiny newspaper, The Italian Insider, which had been the cause of so much joy—and so much trouble.

Phillips had founded the paper in 2010 after three decades as a foreign correspondent for broadsheets, tabloids, and wire services. He had been the man on the ground in places as diverse as Paris, the Balkans, and Lebanon, as well as Rome-bureau chief for The Times of London but also a wire reporter and Fleet Street hack. When The Times summarily fired him after years of service—“office politics,” he grumbled—Phillips decided to launch a publication of his own, in the hope of eventually selling it for a tidy profit.

The Insider is a curious business venture, a paper broadsheet with a print run of 20,000 that calls itself “Italy’s Number 1 English language newspaper.” (“It’s No. 1 because it’s the only one,” Phillips admits.) It is full of stylistic quirks (“dllrs” for “$,” “boffins” for “scientists”) and macabre Fleet Street doggerel (man walls in dead mamma’s corpse to bilk her pension).

From ads and sales, it nets barely $30,000 in a good year. Phillips doesn’t draw a salary, though he allows himself a generous expense account. The only other full-time staffers are interns, including one who was paid a pittance and whose quixotic duties included campaigning for a Nobel Prize on behalf of a Neapolitan poet who also happened to be an investor in the paper.

And yet the Insider has proved hugely important. In 2011, Phillips began to receive tips from sources at the United Nations Food and Agriculture Organization, or F.A.O. Established in 1945 to end world hunger, the agency is based in a large Fascist-era compound next to the Circus Maximus in Rome. Notoriously inefficient and opaque, F.A.O. was mired in controversy following the election to the governor-general’s position of José Graziano da Silva, a former Brazilian minister whose tenure began with allegations that he offered debt relief to several Carribbean island states to win the vote.

The United Nations Food and Agriculture Organization headquarters, in Rome.

In short order the Insider’s pages were reporting endless scandal at the heart of the U.N. agency. Stories detailed Graziano’s perceived attempts to fill F.A.O.’s upper echelons with relatives and cronies (fao struggles to contain nepotism scandal); the alleged influence on the agency of a former Italian premier and shady Vatican sects (Vatican ‘saves opus fao jobs’); and the “punitive relocation” of troublemaking staff to Afghanistan and Samoa (fao “vendetta posting” outrages staff).

A few wondered whether some of his phrasing was perhaps a bit close to the bone, but the reporting consistently proved true. Only later would things get out of hand.

Subversive Material

One morning last year, Phillips put on a suit and tie and a thick coat, climbed into his white Saab Aero 93, and began the paper’s monthly, one-man, countrywide distribution. He headed for Caserta, a few miles from Naples.

The Saab swung through potholed streets. A sharp turn gave way to a lagoon-sized puddle into which the car plunged, resurfacing narrowly. Phillips edged around the corner and approached a large metal gate. Heaving himself from his vehicle he walked, slightly hunched, rang the buzzer, and croaked, “Italian Insider.”

The gate opened and Phillips trundled through, stopping in front of a nondescript warehouse filled with huge printing presses. A man with graying hair welcomed him and gestured at the new edition of the Insider piled in three large stacks. eu biffs italian racist discrimination of uk lecturers, a headline on the front page declared.

Phillips hauled the papers into the trunk of his car, stuffing the remainder in the backseat, before handing the printer-operator an undisclosed amount of cash. “That sum is a trade secret, not for publication,” Phillips confided darkly. “Otherwise F.A.O. might come down and give them a few thousand and ask them not to print the paper anymore.”

Pope Francis with F.A.O. director general José Graziano da Silva.

Parking on a grassy curb, he tore a copy of the new edition from the straps binding each stack together and flipped through the pages, checking for typos. Finding no serious errors, he revved the Saab’s engine. They set off for the tiny island of Procida, a sleepy, brightly colored seaside town a mere 45 stomach-turning minutes from Naples on the hydrofoil.

He had reserved a dozen or so copies for his friend David Petrie, a retired Scottish professor of English literature and one of the paper’s few stakeholders. Petrie is tall, affable, heron-like, with a white beard and red face, and lives in Procida in a kind of exiled bachelordom, bedding alone in a chaotic villa by the beach. Phillips handed Petrie 20 copies for distribution among fellow islanders; others would sell at local newsstands for €3. If they sold.

They perused the new issue. Phillips looked at a cartoon depicting Italy’s aging president, Sergio Mattarella, propped up by scaffolding, wondering whether it was a bit much. “I worry this could get us pulled from the newsstands,” he muttered. “Vilification of a public figure.”

Petrie was unmoved. “I think it’s fine.”

“There’s still a law,” Phillips reminded him. “Papers are supposed to deposit one copy with the local police station to check for subversive material or whatever … ”

“Fascism.”

Phillips had been guarded ever since 2015, when he was summoned to a police station in Rome for a surprise interrogation. It was there he was told he had been sued, under a Mussolini-era law designed to silence subversives, for defamation by four F.A.O. officials—and by F.A.O. itself.

In the past, the club had been a debauched redoubt for the daring—a place of Vatican intrigue, exorbitant expense accounts, spirited visits by Gore Vidal, and newspapers bankrolled by the C.I.A.

It ought to have caused widespread moral outrage, Phillips believed, or at least an outpouring of support—but it didn’t, apart from a few token contributions and strongly worded press releases from NGO legal-defense funds. When the hearings began, in a run-down, brutalist courthouse just north of the Vatican, Phillips was accompanied by only a few close friends and colleagues and felt unnerved in the presence of the five diplomats and their lawyers.

One by one the plaintiffs made their cases. The prosecution cast Phillips as a dishonorable yellow journalist running a “clandestine paper” and a “personal blog.” The word “blog” especially wounded him.

The prosecutors also made a big deal of certain indecorous turns of phrase used by Phillips, but much of his allegedly libelous copy—often written in acerbic Fleet Street satirical style, impenetrable to outsiders—appeared to have been either willfully or accidentally distorted in translation. The defense demanded an expert witness to counter the mistranslations, and Phillips knew the perfect man for the job: Torquil Dick-Erikson, perhaps the world’s foremost—if not only—expert in Anglo-European comparative criminal procedure. A lively septuagenarian with the severe, caustic manner of a Victorian schoolmaster, Dick-Erikson was a superb get: not only was he intimately familiar with the Italian court system, but he also had impeccable locution in the relevant tongues.

Philips’s case went all the way to Italy’s Supreme Court, in Rome.

He walked the court through a debunking of the translation, perhaps the most stunning of which pertained to a Romanian plaintiff. “The foul-up they made,” Dick-Erikson recalled, his diphthongs vast and inimitable, “was that some Romanian had been given an undeserved promotion, and John described the job he had done as being ‘piss-poor.’ This was translated by the translator as ‘piscione’—as in, a ‘bed wetter,’ someone with weak bladder control!”

He cackled without mirth.

“It’s pretty weird that a person who does not know English has to judge whether English words are criminally defamatory or not,” he harrumphed. “It means the judgment is basically completely in the hands of the translator.”

The whole process was rotten, in Dick-Erikson’s view. “Instead of looking at the facts of the case, people think, Who is this between? It’s between a major U.N. organization with hundreds of employees producing millions of revenue in Rome against what the Italians would call a half-cartridge journalist who runs a small newspaper for English speakers.”

The court ultimately ruled against Phillips, and he appealed on the grounds of serious procedural errors made during the trial, including the apparent intimidation of a key witness. Short of being found innocent on merit, he hoped he might at least be able to grind the case through the notoriously slow Italian legal system until it expired midway through 2022.

“Who is this between? It’s between a major U.N. organization with hundreds of employees producing millions of revenue in Rome against what the Italians would call a half-cartridge journalist.”

Mere weeks before that deadline, seven years after the ordeal began, a final hearing took place at Rome’s opulent Supreme Court. Phillips’s lawyers reeled off the appeal court’s supposed errors, but their surgical masks made their arguments almost inaudible. The judges, imperious and impassive in their flowing black robes, paid little attention; the plaintiff’s lawyers appeared to doodle distractedly in their notepads. By evening, a verdict came, and Phillips was ordered to pay $1,086 in fines for the criminal charge, $87,000 in civil damages and legal costs, along with a $3,250 fine for having made an appeal that the judges deemed “inadmissible.”

“You can’t win them all,” Phillips said with a wry smile. Privately, though, he was fuming. The negligible punishment for the criminal charges suggested the libel itself was minimal, and Phillips read the exorbitant additional costs as a warning against reporting on F.A.O. in general.

Together the damages are almost triple what the paper earns in the average year. Manrico Andreozzi, Phillips’s lawyer, said the plaintiffs had tried to secure immediate payment of the damages before the appeal, entreaties he ignored. He suspected they wanted to simply shut the paper down as quickly as possible, or at least intimidate Phillips into giving up. Notably, F.A.O.’s relatively new Chinese management, which vindicated much of Phillips’s reporting by firing various officials exposed under Graziano, has for some years now sought to distance itself from the case.

Phillips distributes his newspaper from the trunk of his Saab Aero 93.

Phillips launched a GoFundMe campaign to help pay the damages. It managed to raise just over $20,000 in three years, but that barely covers the legal costs, and he faces imminent financial ruin. “I’d need 10 years to raise the money owed now,” Phillips said.

He considered what he might do next. He is thinking of taking the case to the European Court of Human Rights. “Or maybe I’ll find an opening in Samoa,” he postulated. “Get a job at The Samoan Insider, join all the exiled F.A.O. staff … ”

At the end of his whirlwind distribution tour across Southern Italy, Phillips stood looking out over the coast from Procida, beat from a day of travel. He stared grimly at the glittering infinity of the Tyrrhenian Sea. “You never stop publishing,” he said. “I don’t think journalists should ever retire. Inevitably you’re going to slow down a bit, but—but it’s a shame not to use all that accumulated experience and knowledge.”

True to form, he has continued to publish investigations into F.A.O. “I don’t see the point of it really, giving up the fight,” he said.

Night fell on Procida, and Phillips joined Petrie for dinner at a local restaurant, at which they were the only customers. Over sea bream, steamed potatoes, and a bottle of red, they began to talk about journalism. It wasn’t what it used to be, they agreed.

“Have you read The Scotsman lately?,” Petrie asked. “It’s yesterday’s Times! Journalists used to terrify politicians—they had these huge campaigns. They wouldn’t have the resources for that now.”

Smirking, Phillips said, “Only the Insider is carrying the flame.”

They laughed, and polished off their meals. When it came time to pay, Phillips asked what the damage was, then shrugged, took out his wallet, and expensed the bill to The Italian Insider.

Ben Munster is a Rome-based journalist