Just when you thought Silvio Berlusconi’s secrets couldn’t get any more squalid, the Italian prime minister lowers the bar. The 74-year-old media mogul cum head of state is gearing up for an autumn of “whack-a-mole” as he tries to smash down the lurid scandals that keep popping up around him. He is currently on trial for allegedly procuring an underage prostitute, tax fraud, bribery, and corruption. Pillow talk, gossip, and detailed descriptions of his sexual prowess and insatiable libido have become such standard fare in the daily Italian press that they no longer shock the nation. His bromance with Col. Muammar Gaddafi has called into question his mental state when choosing friends. But last week, Berlusconi sank even lower when the Italian press printed excerpts of a tapped phone conversation in which he said he couldn’t wait to leave Italy because “this shitty country makes me sick.”

The conversation was tapped as part of a broader investigation into Berlusconi’s alleged girl-fixer Gianpaolo Tarantini and his wife, Angela Devenuto, along with newspaper editor Valter Lavitola. Tarantini and Devenuto were arrested last week, charged with blackmailing Berlusconi. Lavitola, who is in Central America, also faces similar charges for his role as a messenger between Berlusconi and the corrupt couple. Tarantini is already in deep trouble because of Berlusconi, facing charges for procuring prostitutes for the prime minister’s steamy sex parties in Rome and Sardinia during 2008 and 2009.

Tarantini allegedly supplied around 30 women for nearly 20 parties, but he maintains that he footed the bill for the call girls and that Berlusconi had no idea the girls were paid. Instead, Berlusconi is said to have thought they were simply guests with benefits for him and his cronies. Before his arrest, Tarantini was set to enter a plea bargain in the prostitution case to keep it from going to trial to help his pal Berlusconi. After all, details and witness testimony by women who were paid to service the prime minister would be highly embarrassing, especially against the backdrop of his own trial for having sex with an underage prostitute set to resume in October.

For a man who has been on trial more than a dozen times in the past decade, Berlusconi as victim is a rare occurrence in Italian courts, and he denies that the trio were blackmailing him. He doesn’t deny paying Tarantini, but he says it was simple generosity. "I helped a family with children who found themselves and continue to find themselves in very serious financial difficulty. I didn't do anything illegal: I limited myself to helping a desperate man without asking for anything in exchange."

But prosecutors say Tarantini allegedly sought to capitalize on Berlusconi’s desire to keep the prostitution case out of court. He was overheard in tapped conversations directing Lavitola to hold Berlusconi’s feet to the fire, threatening that unless he kept paying, Tarantini might be tempted to change his defense in the prostitution trial and let it go to court. In court documents obtained by The Daily Beast, the prime minister is said to have agreed to pay a sum of €500,000 followed by monthly payments of €20,000 that covered the rent and expenses of a posh apartment. Berlusconi’s personal assistant Marinella Brambilla developed a coded language with Lavitola, referring to payments as “photos to print.” If Brambilla “could print the photos,” it meant payment was imminent; if she “could not print the photos,” it meant the money wasn’t ready.

As the investigation into the blackmail charges continues, Tarantini likely won’t succeed in entering any plea agreement for his prostitution case—meaning Italy will have to brace for even more lewd details about Berlusconi’s bedroom antics. His own underage-prostitution hearing reconvenes on Oct. 4, and it is possible that the two cases will run in tandem, with far more details of dirty old men and their sex lives than the Italian public wants or deserves to hear.

Meanwhile, Berlusconi is losing his grip on “shitty” Italy. He is having a difficult time passing an austerity package needed to balance the books and save Italy from a spiraling economic crisis. Investor confidence is at an all-time low, and Italy’s current debt has exceeded 120 percent of its gross domestic product. A general strike scheduled for Sept. 6 could prove chaotic, especially if protests become violent. No doubt Berlusconi’s disparaging remarks about the country he runs mirror exactly what many Italians think of him.