Does Big Government Lead to Smaller Government?

Greg, a loyal reader,, emails me this query:

I live near Chicago Illinois. It must be one of the least libertarian places in the US. Chicago is famous for its preposterously large (and horrendously run) government. All this government has created very large operating deficits for the city, county and state. The government has gotten so big and burdensome that Chicago has had to think creatively to solve its debt problems.

Here's my dilemma: To solve their budget problems, Chicago has ironically been at the leading edge of some very libertarian-friendly policies.

For example, the city became one of the first municipalities to privatize a major tollway (the Skyway)... and is now trying to privatize a major airport (Midway). Chicago also privatized its parking meter operations. With that privatization, parking rates rose to a more competitive and unsubsidized rate. This deal has been criticized - but now more parking spaces are available and the company that runs the meters has upgraded all the facilities so that now people no longer need 500 quarters to feed the meters... you can pay with cash, credit card, etc.

The obvious paradox is that as government gets worse (and budgets get bigger), the city has resorted to more libertarian-friendly options. So what's the hopeful libertarian to do?

So does this mean that Frankin Roosevelt, Lyndon Johnson, George W. Bush, and Barack Obama are big time libertarians?