Standing in the sun outside Milan’s San Raffaele hospital last September, Silvio Berlusconi, the great survivor of Italian politics, recounted the story of his latest remarkable escape.

“I told myself: ‘You have got away with it again’,” the tanned and grinning tycoon told his cheering supporters, recounting his battle with Covid-19. Having contracted the virus on holiday at his villa in Sardinia he developed double pneumonia while already recovering from a heart attack.

Berlusconi, who for decades has seduced Italy with tales of entrepreneurial daring and stamina, insisted that his viral load had been “the highest among tens of thousands of patients” at the Milan hospital.

The message was clear: after holding his business and political empire together through multiple scandals, legal investigations, business feuds and electoral setbacks, the man they call Il Cavaliere was not going anywhere.

The 84-year-old Italian magnate, who has unexpectedly returned to government this year, is now planning his last act: succession.

Talking to journalists after a meeting with Italy’s president in 2018, the leaders of centre-right coalition Giorgia Meloni, left, of the Fratelli d’Italia party, Matteo Salvini, right, of the far-right party Lega party and Silvio Berlusconi, centre, of the Forza Italia party

The February earthquake in Italian politics that saw Mario Draghi, the former president of the European Central Bank, become prime minister of a national unity government, has given Berlusconi an unlikely reprieve. Having been out of office since 2011, the new coalition brought Berlusconi’s Forza Italia, now the smallest of Italy’s rightwing parties, back into power and gave him three ministers.

Back in the limelight once again, he is looking to cement his legacy. In a bid to secure a long-term role for his political party, Berlusconi is negotiating the formation of a centre-right political bloc — in what could be the last big gamble of his political career.

“It is my final objective, which I have been thinking about since 1994 and which today can finally be achieved,” he told Fortune Italia last week.

His political return could also provide a fillip to the family media business which has struggled over the past decade when he was out of power amid deep structural changes to the industry.

Silvio Berlusconi addresses a rally in Rome in 2019

The question facing one of Europe’s longest-standing and most controversial politicians and businessmen is what will remain after he is gone.

Can his children guide the family’s media empire through the challenges of a transformed advertising market and threats from US streaming giants like Netflix? And does Berlusconi’s much diminished political party, which has shaped Italian politics since the early 1990s, have a future without the businessman who built it in his own image? Or will it simply fade away?

“No one inside Forza Italia really believes that the party can exist in a meaningful way without Berlusconi,” says Daniele Albertazzi, an academic at Birmingham University. “If he named a successor he could have helped the party survive after him, but it remains entirely dependent on his personality and even his funding.”

Even before the day in 1994 when the then 57-year-old Milanese tycoon stunned Italy by declaring he was “entering the playing field” of national politics, Berlusconi had always operated in the messy intersection of power, media and business.

As he spoke, the sclerotic and corrupt party system of the so-called First Republic was collapsing. Berlusconi’s Forza Italia was built on a single, powerful idea years ahead of its time: aspirational anti-politics.

“If you listen back to that speech now it is all still there, he hasn’t really changed a single word over his career,” says Albertazzi.

“He says, ‘I am an outsider, I created an empire for myself and I can do the same for you. The politicians are corrupt and have betrayed you, and I am the man to lead the country’.”

Yet support for Forza Italia has collapsed since Berlusconi was ejected from office in 2011. Having won 30 per cent in the 2013 election, Berlusconi’s share of the vote fell to 14 per cent in 2018 and the party currently polls in the single digits, overtaken by a new generation of rightwing nationalists led by Matteo Salvini’s League and now Giorgia Meloni’s Brothers of Italy.

For its entire history, Forza Italia has been built around the image of Berlusconi. He has not named a successor and many in Rome believe it risks melting as soon as he is gone.

But Antonio Tajani, a senior Forza Italia leader and a Berlusconi loyalist since the early 1990s, says his party has a deep bench. “We have many young MPs working towards the future,” he says. “But today Berlusconi is our leader.”

Tajani, a former president of the European Parliament, describes how Berlusconi runs the day to day business of his party via Skype from his 17th century Villa San Martino.

“He is very active and very engaged. Getting Covid was a problem for two or three months but his health is much better now, and I want to be optimistic.”

But in May, former Forza Italia member Giovanni Toti, the governor of the Liguria region and an ex-Mediaset news editor, launched a breakaway centre-right party named Coraggio Italia, triggering a mini-exodus of Forza Italia lawmakers.

Michaela Biancofore, one of 11 MPs who left the party to join the spin-off and famed for being one of Berlusconi’s staunchest supporters, says the party is no longer the same after what she calls Tajani’s “takeover”.

“I’m leaving after Berlusconi left . . . Of course he’s still there, he’s the leader, but there are people who take advantage of the opportunity of being close to him, using him like a plasterboard cut-out,” she told Italian daily La Repubblica.

Berlusconi is currently locked in negotiations with Salvini’s League about a form of merger of the two parties that would create a single rightwing group in what could be his last throw of the political dice.

“Our task is to build a republican party, like the US one, where the centre and the right [work] together to rule the country,” Berlusconi said, speaking virtually at a party event last month.

A merger would allow Berlusconi to leverage what is left of his political influence inside a bigger tent, and likely extract favourable terms from the League ahead of general elections in 2023. Yet there is disagreement in the Berlusconi camp over the move, with some Forza Italia loyalists fearing its more centrist platform will be devoured by Salvini’s anti-migration politics.

While Tajani believes “this is an idea for the future”, the three Forza Italia ministers in Draghi’s government oppose the initiative. Fedele Confalonieri, chair of Mediaset, the broadcaster Berlusconi founded in the late 1970s and which would become Italy’s first privately owned national TV network, is also against the idea.

“I told Berlusconi I don’t agree,” he says. “Forza Italia’s identity is liberal, truly liberal. Of course, if you don’t water yourself down, everything can be done, but these operations must be prepared over time”.

Berlusconi’s media empire has always been deeply interconnected with his political power. By controlling the largest commercial broadcasters in Italy, he could ensure blanket favourable coverage for Forza Italia. When in office, he was subject to multiple legal challenges over conflicts of interest.

In the mind of his eldest daughter, her father’s political career has been a hindrance to their family business.

“The hate campaign against my father hit our companies,” says 55-year-old Marina Berlusconi, the eldest of Berlusconi’s five children and chair of the Fininvest family holding company. She describes “constant accusations of [some kind of] conflict of interest which in reality never existed [and] that only ended up undermining our business strategies”.

Others have disagreed. In 2014 a group of economists published research showing that, based on an analysis of quarterly advertising expenditure between 1993 and 2009, Mediaset’s market share had consistently increased during the years Berlusconi was in power and declined when he was not.

While domestic legislation is arguably less critical for Mediaset now than in the past, a loss of influence in the corridors of power may also be felt in the boardroom.

The media business is now formally in the hands of his children. “I consider myself the luckiest of daughters,” says Marina Berlusconi. Pier Silvio, her younger brother by one year, is chief executive of Mediaset and also sits on the Fininvest board, as do their half siblings from their father’s second marriage to Italian actress Veronica Lario, Barbara and Luigi. Eleonora Berlusconi, the middle child from the Lario marriage, does not hold an executive role at her father’s companies.

Marina, who is married to a former first dancer of Milan’s La Scala and built a reputation as a fierce negotiator, says she has learnt business at her father’s side for decades.

“I’ve had the privilege of observing him from a close range and [have understood] his method and his values,” she says. “His skills are so unique that genetically inheriting even only part of them would have been miraculous.”

Pier Silvio Berlusconi, Mediaset’s chief executive and younger brother of Marina, at a press briefing in 2017

After their father fell ill with Covid, rumours began to surface in the Italian press about a bitter row between Marina and her younger half-sister Barbara. The family has staunchly denied any rift, presenting a united front to the public.

Yet the media empire Berlusconi’s children will inherit from him finds itself in a much diminished position in an industry transformed from when their father pioneered commercial television in the 1980s.

While Mediaset continues to dominate domestic commercial broadcasting, it has merely kept its share of a steadily shrinking pie. As Italy’s economy has flatlined for two decades, Mediaset’s revenues fell from €4.3bn in 2010 to €2.6bn last year.

“The Italian TV market is a shadow of what it was pre-financial crisis,” says Richard Broughton, research director at UK-based Ampere Analysis. The total Italian advertising market spend, including TV, online, print, radio and out of home, was worth around €9bn a year in 2007, he says, but had shrunk to €7bn last year.

At the same time, an increasing amount of advertising spend in Italy is going to online platforms such as Facebook and Google. In 2008, television ads made up 48 per cent of the total Italian market. Today that share has fallen to 39 per cent, according to Ampere.

As new entrants such as Netflix steal viewers from incumbents, and newly enlarged foreign competitors such as Comcast, which acquired Sky in 2018, and Warner Discovery pump billions of dollars into a global content war, analysts say it will be a Herculean task for Mediaset to keep up.

“Falling revenues mean you can’t spend as much on original content as international competitors, so you risk losing more viewers,” Broughton says. “It is a very difficult problem to solve. This is a problem for many broadcasters in Europe but the Italian companies are in a more perilous situation.”

Confalonieri, the Mediaset chair, has been Berlusconi’s friend and ally since their 1950s adolescence in a booming postwar Milan.

“We went to the same school, we started hanging out because of our shared passion for music. I played the piano and he sang well, Yves Montand, Frank Sinatra,” he says. “We stayed friends for our whole life even though I fired him from our little orchestra when we were 19.”

Berlusconi, and his media empire, according to Confalonieri, are in rude health.

“Mediaset is doing well,” Confalonieri says. “Of course it has to face the competition of the various Amazons and Apples but our distinctive characteristics are always valid. If you want entertainment and news you go local, not global. Domestic politics or news about your next door neighbour are always more interesting than world news.”

Marina Berlusconi says the family remains deeply committed to commercial television, and believes that her strategy of building pan-European scale will repel the American tech giants. Mediaset has operations in Spain, and has a stake in German broadcaster ProSieben.

Pier Silvio Berlusconi attends Mediaset’s general assembly to adopt its plan for a European holding company in January 2020

“The digital revolution is upsetting and it is twice as difficult to face OTTs [‘over-the-top’ providers such as Netflix], for their incredible strength but also for the total absence of limits and rules in which they are allowed to operate,” she says.

“Mediaset is among the main protagonists at a European level. We believe it has a solid future before it and we can make it even stronger thanks to the international mergers we are working on.” Following the truce with French conglomerate Vivendi, Mediaset is ramping up plans for a Netherlands-based pan-European broadcaster.

However, it is not clear if this strategy will work, given the lack of synergies between European broadcasters and their audiences’ different languages and viewing preferences.

“Germans don’t tend to want to watch Italian shows,” says Broughton. “You can plough lots of money into an Italian original but it will do well in Italy and not anywhere else. Cross-border consolidation of broadcasters in Europe might address some problems but it is not a short-term fix.”

As Berlusconi enters the twilight of his career, his family and allies continue to battle over his legacy.

For his numerous critics he is a proto-Trumpian billionaire-outsider whose misrule of Italy seeded both the anti-politics of the Five Star Movement and also the high technocracy of the Draghi government.

“He is the father of the idea that politics and politicians are dirty and need to be replaced by something else,” says Albertazzi.

For Marina Berlusconi, the country’s travails in the decade since her father left office is evidence that his critics misunderstood the complexity of running the country.

Back in the limelight once again, Berlusconi is looking to cement his legacy

“In the face of all these changes across the past 10 years, many people, including the most hostile to my father, began asking themselves some questions,” she says.

For Confalonieri, Berlusconi has already become a historical figure. “When Berlusconi approaches the end of his career, and we’re getting there, he’ll be portrayed as a great businessman who went into politics with an entrepreneurial mentality . . . applying techniques and opinion poll strategies to politics”.

Yet the world he and the teenage crooner Berlusconi inhabited, long before social media and Netflix, is gone. The question for the next generation of Berlusconis to answer is whether the magic can continue as their proximity to political power fades.

“These guys are from a different world,” says Albertazzi. “The businesses may continue but the Berlusconi way of doing politics is already dead”.