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As a bitter election reaches its climax. Are the Milanese about to turn their backs on their former favourite son? Wearing an elegant silk jacket, carrying a white Dolce & Gabbana handbag and sporting her customary silver eye shadow, the beleaguered mayor of Milan, Letizia Moratti, cut an incongruous figure as she scrunched across the gravel at an old Gypsy campsite in Milan last week. The 1,500 Gypsies who once lived here have long gone, which is why Moratti had brought the TV crews with her. “When I first came here, I saw an undignified way of life. Now there are zero Gypsies,” she said, before listing the other Gypsy settlements around Milan that she plans to shut down if re-elected this weekend. Moratti’s tough talk matched her mayoral campaign, which has been the most vicious and xenophobic in living memory. This is Silvio Berlusconi’s city, the place where he made his fortune and established his power base. The left has not had a look-in here for two decades, but now Moratti, who represents Berlusconi’s Freedom People party, is in trouble – partly because of Berlusconi’s “bunga-bunga” party-related scandals – and the politics of Milan have turned extremely nasty. Insults flew and there was brawling on the city’s streets after Moratti’s opponent, Giuliano Pisapia, a lawyer and former communist MP, beat her by 40,000 votes in the first ballot two weeks ago. As the run-off vote takes place and there is a feeling that the unthinkable could happen: Berlusconi could lose control of Milan. “It is hard to beat the vulgarity and violence of Italian politics today, but this campaign has excelled,” said Gian Antonio Stella, a columnist at Corriere della Sera . Berlusconi has made the job of holding Milan a personal challenge as he confronts plummeting polls and whispers within his coalition that he has lost his populist appeal. Should Milan fall, fearful supporters whisper, Berlusconi may not be far behind. “If Pisapia wins, Milan will became a Muslim town, a Gypsyville of Roma camps, a city besieged by foreigners,” Berlusconi has warned in one of a series of increasingly irate video messages on his website. He told one TV interviewer that anyone voting for the centre-left had “left their brains at home”. Meanwhile, young activists brought in from throughout Italy fanned out across Milan telling locals Pisapia would open “injection rooms” for drug addicts. “If Pisapia wins, there will be a boom in rapes and prostitutes on the streets,” said Massimo Corsaro, a Freedom People MP. A hardworking city that generates 3.1% of Italy’s gross domestic product, Milan gave Berlusconi his first break as a property developer and he later built his TV empire, Mediaset, there. It was the prospect of a former communist taking Milan from him that drove Berlusconi to hijack Moratti’s campaign, showing up at her rallies to make wild promises about tripling financial assistance to the elderly. Currently facing four trials in Milan, including the Rubygate trial, where he is accused of paying a Moroccan teenager for sex, Berlusconi also sought to win votes by insulting the judges from the court steps, referring to them as “a cancer”. Last week a clearly embarrassed Barack Obama was lectured by Berlusconi on the persecution that he believes he faces when they met at the G8 summit in Deauville. “Berlusconi is locked in his bunker and has lost all contact with reality,” said Antonio di Pietro, leader of the opposition Italy of Values party. “He hoped to win votes by showing up for his trials, but few people showed up to cheer him and it turned off the moderate voters here,” said supermarket clerk Roberto Paternoster, 25. Moratti made her own mistakes, accusing Pisapia in a TV debate on the eve of the first round of voting of hiding an old conviction for car theft, when in fact he had been acquitted. Hours later, Pisapia had taken 48% of the Milan vote to Moratti’s 41.6%. “Berlusconi’s big mistake was to think Milan would be frightened by a middle-class leftwinger like Pisapia,” said Stella. Ignoring calls from his own party to lower the tone ahead of the run-off, Berlusconi gave speeches on five TV stations in one day, prompting Italy’s TV watchdog to dish out fines totalling €800,000 (£693,000) for violations of fair airtime rules before elections. Back in Milan, an incredulous Pisapia alleged that someone was placing fake Gypsies in street markets to hand out leaflets bearing his name, and fake workmen were knocking on doors to tell locals that a huge mosque was about to be built on their doorstep. Il Giornale , the Berlusconi family-owned newspaper, which has stoked the poisonous atmosphere by attacking bishops who dared to criticise the xenophobic mood, claimed that Pisapia’s accusations were unfounded. “Even his magistrate friends won’t believe this,” one editorial suggested. Various Berlusconi allies have joined the fray. “I live and breathe this city and Milan does not want to become a Gypsy town,” said Daniela Santanchè, the fiery minister who founded the Movement for Italy. She was backed by Giuseppe Cali, 23, one of the Freedom People activists in Milan’s Piazza Duomo on Thursday night for a Moratti rally and concert. “If I go into a park with my girlfriend, I just don’t feel safe if there are groups of foreigners there,” he said. “Many Milanese have moved out of town, and we now have half a million pensioners cheek by jowl with 200,000 immigrants,” said Ettore Albertoni, a former regional governor with the Northern League, the devolutionist party on which Berlusconi depends for support in parliament. But the League is tiring of Berlusconi’s numerous scandals and fears that the media magnate’s ranting at judges may be alienating voters. Umberto Bossi, the rough-spoken leader of the League, has failed to show up at several rallies where he was due to share the stage with Moratti. “Milan is so important for Berlusconi because it is where the alliance with the Northern League was forged,” said Tito Boeri, an economist at Milan’s Bocconi university. “If he loses Milan, the alliance may collapse.” There was further angst for the Moratti camp when, at the last minute, star act Gigi D’Alessio pulled out of a concert in support of the mayor, claiming that he had been insulted by Northern League representatives because he hails from Naples in the south of Italy. The job of entertaining Berlusconi’s flag-waving activists fell, bizarrely, to Bryan Ferry, who gamely performed a medley of hits. Hardly noticed by the press, Pisapia is out on the stump every day. Last week he spent a hot Thursday afternoon giving an off-the-cuff speech to 400 residents in a park in the working-class Quartiere 8 neighbourhood on the edge of Milan. As children milled around and a jazz band played, Pisapia showed little grasp of skilful oratory, but drew applause as he talked up plans to open new markets to bring communities back together. “You see, Milan the city is more tolerant than Letizia Moratti,” said Nino, a taxi driver and Pisapia supporter. An hour after the Democratic Party (PD) candidate left, the event was still going strong as free plates of fava beans and wine in plastic cups were handed out. “You don’t see a party atmosphere like this often in Milan,” said student Jacopo Ceccerelli, 23, who pointed out that in a primary held to find a candidate to represent the opposition, Pisapia had beaten the PD’s chosen man. “People here think he is their candidate, not someone handpicked by party officials in Rome.” If Pisapia does win, it will be one of the shock results of recent political history in Italy. Stella believes that, against the odds and after an extraordinarily vitriolic campaign, it could happen. “Everything tends to start in Milan, from the Risorgimento, to socialism, fascism and the ‘clean hands’ investigations into corruption,” he said. “Silvio Berlusconi was born here too, and it is possible his era will end here.” Silvio Berlusconi Italy Europe Tom Kington guardian.co.uk