"You bankrupt Greeks, why don't you sell your islands?"

That advice from German newspaper Bild-Zeitung was a bit of tabloid whimsy, but no one can doubt that Athens faces an Olympian task in shedding assets to help pay off the biggest debt in the euro's history.

Greek Prime Minister George Papandreou's Socialist government launched its privatization regime on June 6 when it struck a deal to sell 10% plus one share of Hellenic Telecommunications Organization SA, or OTE, to Deutsche Telekom AG for €400 million. As the terms of its €110 billion international bailout now stand, the government still must sell a further €49.6 billion ($72.8 billion) worth of state assets by the end of 2015, with the first €15 billion of that possibly due this year, to avoid a sovereign debt default that could well destabilize the European monetary union and global financial markets.

The OTE stake sale was simple and straightforward compared to what lies ahead. Exercising a put option from a 2008 shareholders agreement, Athens easily found a buyer in Deutsche Telekom, which will own 40% plus one share following the deal. The government has said it may sell an additional 6% stake.

Under normal circumstances, Greece would have no difficulty auctioning off properties such as Opap SA, Europe's largest publicly traded gambling company; the Piraeus and Attica ports; and top domestic electricity supplier Public Power Corp. SA. A long list of financial advisers, including Deutsche Bank AG, Credit Suisse Group and Rothschild, will help with the sales. But of course times are anything but normal.

Papandreou, midway through his term, is under increasing pressure to show fast progress on asset sales and budget cuts to secure a follow-up to last year's bailout by the European Union and International Monetary Fund. At home, he faces opposition within his own party and public outrage at the latest austerity measures. At the same time, many Greeks are now more open to the notion of trimming the public sector and selling off some state-owned assets.

The privatization program is part of a broader plan to help Greece slash the EU's highest debt ratio, projected to peak at 166% of gross domestic product next year. "The Greek government needs money to pay current bills," says Fredrik Erixon, director of the European Centre for International Political Economy, a Brussels think tank. "It's a bad strategy, but Greece doesn't have many options."

Addressing concerns of suspect creditors, Greece has pledged to set up an independently managed privatization agency and to issue progress reports measured against quarterly and annual targets. Whether the move is more than a formality remains to be seen, and there are numerous questions about the real value of the assets being auctioned.

Athens has given little guidance about the planned agency or its divestment plans for individual assets. A full inventory of the state's real estate properties has yet to be conducted, though European Central Bank board member Jürgen Stark estimates that the sales potential could be as high as €300 billion.

Many fear that Greece is headed toward a panic-driven fire sale. "In the long term, creditors will actually lose," argues Daniel Gros, director of the Brussels-based Centre for European Policy Studies. "Think about a company in difficulty: Would you allow it to sell its most prized assets?"

On the other hand, risk-tolerant investors may find value. "The political uncertainty increases the level of risk," says Thanos Karvelis, deputy managing partner at Athens' KLC Law Firm PC, "but any experienced investor should be able to put a number next to it." As well, "we're talking about an EU country with a good services sector and good protection for investors, and a banking system that has its problems but one which generally works."

Gambling operator Opap, in which the government holds a €1.5 billion stake, is expected to attract a great deal of interest, as should stakes in the country's motorways and ports.

"On the buy side, there is a considerable amount of funds anxious to invest in infrastructure around the world," says David Simpson, global head of mergers and acquisitions at KPMG, which is advising the Greek government on the sale of Hellenic Defence Systems SA.

As Simpson sees it, the Greek government faces two challenges: "It must ensure that the assets being sold have a good economic model. And it must make certain that the buyers for each asset are appropriately incentivized and supported to ensure that the assets are profitable in the medium to long term."

Potential investors will undoubtedly drive a hard bargain before they walk off with a country's crown jewel -- if not an actual island.