I can still remember vividly the sense of unease I had as I walked past the traffic jams clogging Rome’s roads on a hot day last August. The city had been blocked for the visit of Italy’s new friend, Muammar Gaddafi. As part of the warm welcome he received, Gadaffi was allowed to pitch his Bedouin tent in the beautiful scenery of the Villa Dora Pamphilii, give a public lecture at the University of Rome and even host a ‘convert-to-Islam’ party for hundreds of “glamorous women” who received special invitations to the event. On a previous occasion, Gadaffi had even received a welcome kiss on his hand from a bowing Silvio Berlusconi—a price the PM thought well worth paying for the contracts Italian companies would sign with the oil-rich former colony. My discomfort came from a deep-rooted conviction that the Italian government was not just making an ethical mistake, but also committing a political and economic blunder. Over the last twenty years, Berlusconi has sought to skip boring diplomacy by using his charm and skills as a salesman. And as a diplomat-businessman, he sure knows how to pick his friends. Last December, the Italian Prime Minister chose to boast of his close ties with Ben Ali of Tunisia, Gaddafi of Libya and Mubarak of Egypt. He has received the ruthless Belarusian leader, Lukashenko, with equal enthusiasm. The gamble behind this policy was a simple one: Berlusconi thought he could use his rhetoric to secure close ties with all these resource-rich countries, whilst keeping onside the other world powers who were busy trying to play the same game as him, albeit less competently. What the tycoon-turned-politician neglected was the risk associated with dealing so extensively with such regimes. As the sun appears to be setting on the reign of Gaddafi, the string of ties created between Libyan investment authorities and Italian companies now appears extremely fragile. When news of the riots in Tripoli emerged a couple of weeks ago, the Milan stock exchange lost almost 4 per cent in a day. This provides just a glimpse of what might occur if Gaddafi is toppled. The next Libyan government may well want to punish Berlusconi and Italian business for their close ties with Gaddafi. At that point, Berlusconi’s freewheeling diplomacy-cum-salesmanship will be exposed as both an ethical and political failure.