Give Me Liberty or Give Me Taxpayer Money

Clever libertarians don't just rail against government spending: They do something about it. Facebook investor Peter Thiel took $8 million from New York's pension fund — while setting himself up to avoid millions in taxes.

Clarium's strategy is to take advantage of supposed distortions in the market caused by government intervention. But the New York State Common Retirement Fund has intervened more directly in Thiel's fund, investing $8 million over the course of three months last spring — just in time for Clarium's holdings to crater from $7 billion to $2 billion. The market meltdown didn't help, but Clarium's stated strategy should have thrived in last year's environment, given the Bush administration's repeated attempts to prop up Wall Street. But perhaps it's a sneaky stratagem to bankrupt the government!

While mismanaging public money, Thiel has also made sure he won't be refilling the state till anytime soon. Thiel is actually far less rich than people think. (A Clarium insider tells us, for example, that there's no way he's a billionaire, as Forbes has reported.) His single best-performing investment is not Clarium, but rather his personal 5 percent stake in Facebook, which he purchased for $500,000 and is now conservatively worth $100 million. Sources at Facebook and Clarium confirm that Thiel holds his Facebook shares through a Roth IRA, which allows tax-free withdrawals on his retirement. He'll have paid at most $175,000 in taxes on that fortune. Getting the government out of one's pocketbook — it's every libertarian's dream!

And perfectly legal. Thiel believes neither death nor taxes are inevitable. (When he's not hacking the IRS code, he also funds longevity research.) The only downside? He might be too clever by half. When word gets to Washington of his tax maneuver, populist-rage-filled Congressmen may well call for an end to the Roth exemption. The taxman cometh.