Telecom Italia, once a cash rich powerhouse in the global telecom industry landscape, since the last decade is struggling with a huge debt burden nowadays reduced to the still big figure of nearly 30 bn euros which limits its capital spending capacity as well as its capability of paying palatable dividends to its major shareholders: Mediobanca, Intesa San Paolo, Generali and Spain’s Telefonica, who jointly own the holding company Telco, which in turn controls some 40 pct of the telecoms incumbent since they took it over from the Pirelli group in 2007. When they bought it the stock price was well above 2.5 while early in 2013 it was just above 0.6 euros. The mountain of debt is mainly the heritage of a spectacular hostile takeover carried out in 1999 by a group of raiders nicknamed “Captain Courageous”, who piled up to the purpose financial ammunitions of one hundred trillion lira, the equivalent of some 50 billion of current euros, thanks to a credit facility arranged by Lehman and Mediobanca. Once they got their prize, they managed to transfer the debt from the takeover vehicle to Telecom Italia. At the time of the takeover, TI was freshly privatized and controlled by a hardcore group of shareholders led by Ifi, the holding company of the Agnelli family. Before being privatized in 1998 by the Prodi government, TI was part of state mammoth concern Iri where it used to be the cash cow which fed its parent group finances, always struggling to cover the losses made by other divisions, namely the steel and the shipbuilding business. In the two years following the takeover the Captains disposed several valuable assets of the company and in August 2001 eventually sold it out at a premium on the takeover price to Marco Tronchetti Provera, the boss of tire maker Pirelli, who was then trying to build up his reputation as the new Italian business leader, the man to succeed the Italian king without throne Gianni Agnelli. The timing was unfortunate, as just one month later the terror attack on the twin towers sank stocks across the world. Nevertheless Tronchetti tried to extract further value from TI mainly through financial restructurings and by aggressively expanding in Brazil with the mobile unit Tim. In 2006 he clashed with the government as he tried to sell TI to an American grouping made by AT&T and Mexico’s Carlos Slim but had eventually to give it up to a government sponsored alliance, the same which controls it today. For certain, Telefonica did a pretty good deal: with just a 10% stake it avoided that TI fell into the hands of its Mexican arch-rival, banned competitors from entering the Italian market and entered the control room of its main competitor in the rich Brazilian market. Not so good was for the remaining three Italian partners, who had to write down several times the book value of their investment and repeatedly put fresh money into Telco –possibly among the worst performing asset in their portfolio over the last decade. TI watchers agree that sooner or later the once powerful group should have to give up some valuable asset in order to abate its debt: Brazil and the domestic network infrastructure are the most likely candidates, but both alternatives have big cons too. The network ownership is just what gives TI a competitive edge in Italy against its pretty aggressive competitors, from Fastweb to Vodafone, from Wind to 3. On the other hand side, Brazil is the main source of TI profit and dividends. Since its takeover, the list of assets sold by TI, many of them abroad, was quite long, from the mobile business in Greece to the broadband operations in Germany and France, to historic Italian brands like Italtel, Telespazio, Sirti and Finsiel. In march 2013 it managed to sell the national tv channel La7 to an advertising and publishing group.