Billionaire Calvin Ayre has a $3.5 million, 10,000-square-foot compound in Costa Rica, does business with 16 million customers--mostly in the United States--and is a native Canadian holding the country's passport. He has no allegiance but to his own cause--online gambling. He pays no taxes to the United States or to Canada. He is persona non grata in the United States, is on shaky ground in Canada (which has similar restrictions against online gambling) and was recently raided by Costa Rican authorities, though not charged.

This is the new face of today's international businessman who may hold a passport or two from one country, reside in another and do business in yet another. That leaves loyalties up for grabs, if they exist at all. The name of the game is self-interest, not national interest, and a stateless ego may do more to shake-up the dusty premise of the nation-state than any supranational movement to date.

Businesses have long taken advantage of loopholes in tax laws, favorable registration locales and amenable politicians. The rise of offshore entities in the 1970s was one big step towards separating businesses from national ties. A 2004 report by the Center for Public Integrity uncovered at least 882 oil and gas subsidiaries based in tax havens like the Cayman Islands and Bermuda; in its pre-bankruptcy days, Enron incorporated 780 such vehicles to mitigate taxes and stand above the law, as the prosecution is trying to detail in the current trial of former chiefs Kenneth Lay and Jeffrey Skilling.

The ease of multiple citizenships has added fuel to the fire, allowing individuals to reshuffle a considerable volume of assets. As the number of nation-states grew with the demise of colonial empires and the Soviet bloc, the crossover options for entrepreneurs and investors multiplied. High-net-worth individuals pick not only the best passports, but also the optimal offshore tax havens to get around pesky national ties. A 2003 report by the Boston Consulting Group estimated that these individuals hold $9 trillion, or a quarter of their total assets (cash deposits and listed securities) offshore, resulting in at least $250 billion in tax losses for nation-states.

How to retain control over assets often drives decisions about moving offshore or acquiring "extra" passports. For example, before the 1997 handover of Hong Kong to China, several billionaire businessmen reached for offshore-company registrations and dual citizenships to protect their assets. The sons of Asia's richest and most influential investor, Li Ka-shing (net worth, $18.8 billion), have dual citizenship in Hong Kong and Canada. Billionaire Ronnie Chan, whose family made its fortune in real estate, has dual U.S. and Hong Kong citizenship. That maneuvering proved propitious for the billionaires. After Forbes first published its list of the richest Chinese, several arrests followed, and businessmen wised up. Yang Rong, a multimillionare investor in a state-owned Chinese firm, fled to Los Angeles to avoid detention.

Things get even more complicated when looking at entrepreneurs from the former Soviet Union. Take the three businessmen--the multi-billionaires Alexander Machkevich, Alijan Ibragimov and Patokh Chodiev--now collectively known as the "Kazakh trio." Once stalwart Soviets (Chodiev was even with the Ministry of Foreign Trade), their Soviet passports and identity became meaningless overnight. But how Kazakh are they? Only one of them actually has a Kazakh passport, and none were born in Kazakhstan. Their jointly owned holding company, Eurasian Natural Resources (which recorded $2.9 billion in revenue in 2005), is not even registered in Kazakhstan.

So why are they called the "Kazakh trio", and does that mean their collective allegiance is to Kazakhstan? Ninety percent of Eurasian Natural Resources production comes from Kazakhstan's iron ore, ferroalloy and alumina assets, which the partners allegedly obtained access to via favorable ties to Kazakhstan's long-serving president, Nursultan Nazarbayev. (Kazakhstan's government recently started to re-examine the joint ventures with the trio.) The partners say that they are among the highest taxpayers in Kazakhstan and their corporate entities tout a variety of social spending initiatives on health and education in the towns where mines are located. This is commendable, to be sure, but Machkevich holds an Israeli passport, Chodiev a Belgian one. And all three reside abroad in the UK or Switzerland.

For Machkevich and Ibragimov (who were born and raised in Kyrgyzstan) and Chodiev (who is from Uzbekistan but was fascinated with Japan and worked several years there) the disintegration of the USSR presented several options. Israel offered citizenship to millions of ex-Soviet Jews. Many, like Machkevich, took the offer. So did Mikhail Chernoy, who with his brother partnered with the Kazakh trio on early commodity trading, and Leonid Nevzlin, who has avoided the fate of his former Group Menatep and YUKOS partner Mikhail Khodorkovsky (recently sentenced to nine years in a Siberian prison for tax evasion). Others secured new passports by moving to new countries. Chodiev, for example, went to Belgium. Billionaire Alexander Shnaider, who was born in Russia, built a business based on Ukrainian ties but is a Canadian citizen living in Toronto. So where do national loyalties lie?

In interviews this past winter with Machkevich, Ibragimov and Chodiev in Courchevel, France--where the three were on an extended ski holiday--the closest allegiance I could see was that which the partners and friends had forged with each other and with their twenty-strong clan. A close second would be their respective religious affiliation: Machkevich is very active in Jewish causes, and Ibragimov is a devout Muslim who even declined to have his picture taken on the grounds that it was against his faith. But allegiance to a nation? "Kazakh trio" seems like a misnomer.

That is not to say there are no businessmen who have forged allegiance to their post-Soviet state. Certainly, there are many Russian billionaires who have kept their Russian passports. But some still find it more expedient for them and even their families to live and invest abroad. Take for example, Russian oil tycoon Roman Abramovich, who sold his majority stake in Russia's Sibneft this past fall for $13 billion. He resides in London and owns the UK's storied Chelsea Football Club, but he was also reappointed governor of Russia's distant northern region of Chukotka and has been buying up commercial real estate in Moscow. Another Russian billionaire, Viktor Vekselberg, who also made his money in oil via his stake in TNK (now TNK-BP, Russia's second largest private oil company), was born in Ukraine, now lives in Moscow and promotes Russia's heritage. In 2004 he bought nine Faberge eggs from the Forbes family for a reported $200 million and brought them back to Russia. But his wife and children have been ensconced in the New York area for over a decade--a mixed set of loyalties to be sure, and it is unclear how they would unfold if a choice had to be made.

Perhaps the goal of multiple passports and residences is to avoid having to make such a choice and to maintain the broadest array of options. Certainly, Saudi multimillionaire Khalid Masri, who received an Irish passport in 1992 after investing over a reported million dollars in an Irish pet-food company, may have been interested in a more Western-friendly ID. This phenomenon may gain more momentum as countries create stricter travel rules, as the United States did post 9/11.

Clearly, Czech national Viktor Kozeny was shopping around, allegedly obtaining Irish and Venezuelan papers, in addition to his Czech credentials. Nicknamed "the Pirate of Prague", officials from both the Czech Republic and the FBI investigated him for alleged fraud arising out of privatization deals. At last notice, he was in a Bahamanian prison awaiting extradition to the United States.

This national horse-trading is not new, of course. Athletes, politicians and even the layperson can play the multiple passport game. Olympic athletes regularly train in other countries and go back to represent their homeland--though in one case in 1998, an ice hockey player, Ulf Samuelsson, was kicked off the Swedish team after it was revealed that he held a U.S. passport. New Zealand politician Harry Duynhoven reapplied for his Dutch passport while in office in 2003, causing a stir. Michaelle Jean, Canada's governor general (who represents the Queen of England, the head of state, and carries out her ceremonial duties), was appointed even though she had both Canadian and French citizenship and stated she would relinquish the latter. I myself can apply for dual citizenship in Poland because my parents emigrated from there. (Holding Polish citizenship would permit me to work in any EU member state, sans work permit.)

To date, there has been more of a backlash against companies changing affiliations than against individuals. The accounting firm Accenture, once known as Andersen Consulting, based in Chicago, was accused of tax dodging and anti-Americanism when its partners voted to register in Bermuda. In 2004 the U.S. House Appropriations Committee even voted to block a $10 billion contract awarded by the Department of Homeland Security for Accenture to play a lead role in a border safety program. Every so often, CEO Bill Green has to defend the domicile, stating that the company is an international business and is not running away from the United States. Other companies were forced to stay in the United States when they tried to move headquarters, like toolmaker Stanley Works, which bowed under the combined pressure of congressional heat and worker protests.