From Football Ultras to Cocaine Smuggling: The Wild Life of Alessandro Casolari

I had heard the name Alessandro Casolari on and off for years. From 2016 onwards, when I was researching my book on Italy’s ultras – a cross between English football hooligans and Hells Angels – the nickname “Caso” kept coming up. In the late 80s and early 90s, he had led the ultras in Ferrara, whose football club is known as Spal.

A red-brick city in northern Italy between Bologna and Venice, Ferrara has always felt sidelined, languishing in a marshy land of fog and floods. I used to go there quite often, drawn by its festivals and famous writers and film directors. A few years ago, when I started writing another book, about the Po River, I hung out there again, but I never bumped into Caso.

Then, in December 2024, he called me out of the blue, having got my number from a mutual friend. He was talking non-stop, weaving together stories about Caracas, Medellín, cocaine and Kosovo. He was jumping from one story to the next, and they were all connected by a dozen subplots he had to explain at length. Every other sentence ended “hai capito?”: “you get it?”

I picked up that there had been a murder in 1998, which was how he had ended up at a funeral next to a man who had just won the lottery. That money allowed them both to go to Colombia, which is how Casolari met his wife and made contact with the Farc guerrillas (Revolutionary Armed Forces of Colombia), started working in hostage negotiation and then ended up importing hundreds of kilos of cocaine to northern Italy. It sounded far-fetched, but he seemed to know the whole jungle-to-mirror journey of cocaine. Getting a question in was like chucking a paper plane into a gale.

Around the hour mark he slowed down a bit. He told me had just been “held captive” (his term for prison) for 177 days. “Eighty-two in solitary, hai capito?” That was why he was phoning: he wanted me to write an article denouncing human-rights abuses in Italian prisons. He had, he said, suffered “a broken nose and a compound fracture of the right cheekbone”, thanks to beatings by guards. “When I was arrested, I weighed 74kg; by the end I was a larva, weighing just 61kg.”

“Hang on,” I said. “Why were you in prison?”

“I only gave someone four slaps. That was it.” He said he would send me links to the newspaper coverage, but he wanted me to know it was mostly rubbish because “the police, the judiciary and the Italian institutions are a mafia-infested wormery”. As “a Marxist-Leninist communist revolutionary”, he had declared himself “a political prisoner”.

He only ever spoke the truth, he told me. “My calling card is unequivocal: I’m a loyal person, an extremely sincere person. I never exaggerate or downplay my experiences.” His language – “larva”, “wormery”, that “unequivocal calling card” – was beguiling, even though I was aware he had avoided telling me that bit about the four slaps. (I later learned that the formal accusation – since cable ties, guns and a Taser were involved – was aggravated robbery, kidnapping and the transfer of explosive devices.)

It was a world I thought I knew. I teach and mentor a few ex-offenders. And I often write about criminals. I know how the journalist-criminal dynamic usually ends: one of us betrays the other. Sometimes they feel as if I’ve stolen their story. Or I discover, too late, that I’ve been sold a story that exists only in their head.

So I assumed that with Casolari the relationship, or the story, might be built on sand. But I was fascinated by him because he seemed to take the ultra philosophy – that there has to be confrontation, there must always be a fight – to the next level, while disguising it with charm and eloquence. “He’s verbally very sophisticated,” Maresciallo Maggiore Giuseppe Fenuta, the officer who arrested him after the “four slaps” incident, warned me.

Casolari and I even had a few things in common. His politics wasn’t so far from mine (he a communist, me a communalist). We had both married outside our nationality and had children in their teens and 20s. Like me, he was a freelancer of sorts, another lone hustler. I was interested in what my life might have looked like if the kaleidoscope of fate had been turned a few degrees. So in January 2025 I went to Ferrara to meet him.

Casolari was under house arrest, pending his trial. Because he had a new lover, his wife had kicked him out of the family home and he was renting a small flat just south of the city walls. He was showily courteous. His tough look – skinhead, stubble, boxer’s nose – was somewhat undermined by his goofy smile.

When we got down to business, he started pacing like a trapped animal, talking double-quick, just as he had on the phone. I couldn’t pin down the details on any of the previous stories because he was constantly launching into new ones. He spoke about his time in the army and in prison, about Marx, Bobby Sands, Jesus, Che Guevara and Hugo Chávez. If I butted in, he stopped and listened, examined the idea, and then set off again.

I quickly noticed a logistical problem. We were facing different directions: I wanted to hear all about his past, but he was using me as a sounding board to figure out his next move. There was an Italian being held hostage in Caracas whom he thought he could “bring home” in return for a pardon. Or maybe he would become a mercenary. Or a peacekeeper. He was going to call his friend, Renato Curcio – founder of the far-left terrorist group the Red Brigades in 1970, who had set up a publishing house while he was in prison – to pitch the idea of writing a prison diary. This wouldn’t have been Casolari’s first foray into publishing: he had already co-authored a book about his ultra gang, Gruppo d’Azione. Did I have any advice about royalties? Rather than writing about his life, I felt I might become his careers adviser.

But over the months that followed, each time I found myself in Ferrara for other reasons, I would want a bit more of the story and go back to Casolari’s bedsit. After his house arrest ended in autumn 2025, he began driving me round the city and sometimes we would have lunch with his two sons. We went to Rome together for a conference organised by Curcio’s publishing house.

I was fascinated by him as a character study: he was both a misfit – a short-fused tough growing up in rich and bourgeois Ferrara – but also, in a fairground mirror way, a distorted reflection of this traditionally leftwing city.

He was born in Ferrara in June 1966. His father was the son of local farmers, his mother the daughter of a Sicilian lawyer. He spent 11 years in the private convent school of Sant’Orsola and studied languages – Latin, French and English – at the city’s Ariosto lycée. He read a lot. He had been going to the football on and off with his father since the age of nine, but at 16 he had started hanging out with the Spal ultras (Spal is an acronym of Società Polisportiva Ars et Labor). A subculture born in the 1960s, the ultras were macho fist-fighters. Unlike British hooligans, they were structured hierarchically and were experts at inserting themselves forcefully into local politics. Casolari enjoyed the riotous atmosphere and, with his new friends, developed a lifelong taste for cannabis.

After leaving school in 1984, aged 18, he spent his nine months of military service with the Italian parachute regiment in Livorno. Every six weeks he came home on leave and talked about bringing together the archipelago of Spal’s ultra groups – the Nutty Boys, the Legion of Hooligans, the Estense Ditch, Stoned Again, the Fringe, Astra-Alcohol and many more – into a single unit, thereby making them a better fighting, and lobbying, force. Uniting them all under one banner took cunning and muscle. “Caso was pure charisma,” remembers one of his many exes, who did not want to be named.

On 2 November 1986, at the away game against Padova, a new banner was unfurled, reading: “Gruppo d’Azione”. This “action group” was to be the “military wing” of the west terrace. They were set up to fight ultra gangs from other teams. For home games, they had a different banner, 50 metres long: “Gioventù Estense”, meaning “Estense youth”. (“Estense” is the adjective for the Este family that ruled Ferrara in the middle ages.)

With his black curls, faded denim and maxed-out megaphone, Casolari led the terrace chants. His boys were called “gremlins” because they wore green bomber jackets. Their mottoes – “Hit everything, educate no one”, “City fights and getting shit-faced” – made their interests clear: drugs, violence, thrill-seeking. Every Tuesday, from 9pm, the ultras gathered in Bar Astra. There might be anything from 50 to 200 there, herded by eight members of the “board”. “I always took the final decision,” Casolari told me. In rival cities, the ultras looked to cause maximum carnage as they sang their anthems, “Di legno Siam” (“We’re made of wood”) or – to the tune of Red River Valley – “… the city will be destroyed”. Already off their faces, they would break into chemists to top up on Valium or Rohypnol. Since the birth of the ultra movement, at least 19 people have died in football-related violence in Italy.

Casolari picked up seasonal work weighing and unloading sugar beet in the local factory. He supplemented his income through petty theft. He was first arrested in 1986 for mugging the son of a policeman. He was sentenced to 12 months but never served due to a general amnesty for minor crimes, to reduce the prison population. A year later, aged 21, he began a relationship with a 14-year-old, Annina*. (The age of consent in Italy was, and is, 14.)

Casolari’s men took positions on local issues. In 1989, they staged protests against the city’s plan to bury hazardous waste in local landfills. Casolari organised marches and – a sign of how much the ultras were seen as spokesmen for local grievances – was even welcomed into schools to talk with teachers and students. On one occasion he and his followers interrupted a city council debate to protest against the hazardous waste dumping. “He led a popular revolt,” another ex-girlfriend told me. “He always knew how to talk, what to say.” It made no difference, though. The toxins were buried in a landfill outside the city, and other sites across Emilia-Romagna.

In 1990, he was arrested again, after a fight in a pub, though he didn’t serve a custodial sentence. His time as an ultra boss came to an abrupt halt two years later, at a European under-21s game played in Spal’s stadium. Police had confiscated a box of smoke flares from the ultras, but someone retook possession of the box and the flares were quickly passed around. When Casolari unscrewed the bottom of his and pulled the cord, instead of coloured smoke, it fired a nautical flare that struck a young woman standing nearby, causing serious head injuries.

It emerged from the subsequent investigation that the company, Parente, from which the flares had been bought, had a sideline in other materials and the smoke flares had become mixed up with the nautical ones. The injured young woman and her parents sued Casolari, Parente, the ministry of the interior and Spal. In March 1996, the family was awarded damages of 200m lire (about €174,000 in today’s money). A later ruling divided the damages between the accused, leaving Casolari with 70% of the total to pay.

His life fell apart. He was banned from the stadium. All his future earnings would be taxed for that compensation. He and Annina split up. His parents had a tobacconist in the centre of town selling cigarettes, watches and pens. Later they had a jewellery shop. “I was a dimwit,” he said, “dipping into my father’s wallet, stealing blocks of cigarettes.” “It was always his family,” his younger brother Luca told me wearily, “who paid the price for his adventures.”

Casolari continued to smoke weed and have regular run-ins with the police. In 1995, he was arrested for holding a Nigerian sex worker hostage and was sentenced to nine months, later commuted to “conditional liberty”. (After a year with him in which he admitted to pretty much everything of which he was accused, he denied this one – he said it was a case of mistaken identity – stood out.) He was sent to prison from May to August that year for fighting a carabiniere when – after a long night partying – he drove the wrong way down a one-way street.

At that point, he was just another petty criminal, a street-fighting stoner with sticky fingers. But during those months in prison Casolari met a Colombian who would be the reason he ended up in Medellín, becoming a husband, father and amateur drug lord.

Casolari likes to see himself as a good guy. In his telling, even his wildest escapades begin with an act of kindness. In prison, he met Julio, a Colombian who had been convicted for cocaine smuggling. When Julio’s prison supplies of sugar and pasta kept getting stolen by other prisoners, Casolari and an old ultra mate decided to attack the thugs who were stealing his supplies. From there, a friendship grew.

Casolari introduced Julio to his uncle, a lawyer, who managed to get him transferred to an open prison. They corresponded for years, Julio sending postcards written in courteous English. Casolari has kept them all. There are boxes of archives – diaries, letters and photographs – that pile up in cupboards like a tribute to his career.

On his release in 1996, after working a series of factory jobs, Casolari decided to enrol in the Italian army. “Being a soldier is a proletarian job,” he told me. “The officer class had a few fascists but apart from them, I didn’t struggle with the hierarchy.” He went twice to Kosovo and Bosnia and claims to have served in Afghanistan (though I had trouble verifying the latter). The appraisals from this period – at least the ones he showed me – are, surprisingly, glowing: “lively … loyal … constructive … esteemed”, though one report alludes to his “irritability”. He got shot in the arm in Kosovo. He is now the beneficiary of a veteran’s pension of €1,200 (£1,000) a month.

The army also gave him long leaves of absence. In October 1997, he was at a funeral in Ferrara of an ultra, Luca Sgambellone, who had murdered an old man and then overdosed. At the funeral Casolari met a man who confided that he had just won 66m lire (the equivalent, now, of about €56,000) on the football pools. Casolari suggested that they should go to Colombia to see Julio.

It all seems fantastical: a murder, a lottery win, an international adventure. Casolari appeared to have a super-human ability to bend destiny to his will. Or maybe – I wasn’t sure – it was just manipulation, using people as stepping stones in his grand schemes.

On New Year’s Day 1998, one of Julio’s relatives picked up the Italians at Bogotá airport. They spent a week in the capital and then two in San Andrés, a Colombian island in the Caribbean. It was there that Casolari met his future wife, Ana Eneida Mena Arias. She worked in marketing, one of the few Black people in