George Will's latest on Mayor Daley's privatization policy raised as many questions as it tried to answer. Mostly, it shows how convoluted the debate has become when a conservative pundit raises questions about the efficacy of Democratic mayors and governors selling off city services and infrastructure.

Faced with competitive pressures, fiscally squeezed Democratic-led state and local governments are looking to the privatization pioneers of the 1990s mayors, such as Indianapolis mayor Steve Goldsmith, for a model. Will sees promise here: "By selling future revenue streams, Daley believes, the city can ignite a virtuous cycle: Buying improvements "as quickly as possible" in education and infrastructure can lure people back to the city, thereby improving the city's tax base and cultural vibrancy, which enables further improvements that attract still more residents."

But along with his suspicion of big and unwieldy government, also sees the human nature danger in exchanging recurring revenues for cash in hand: "Unfortunately, Daley's theory -- that it can be better to get a sum X immediately, rather than getting over many years a sum Y that is substantially larger than X -- assumes something that cannot be assumed. It assumes that governments will prudently husband sudden surges of revenue from the lease or sale of assets."

This brings to mind bankrupted lottery winners, and people selling off annuities for much smaller one-off payments. The lottery parallel is especially to the point, as Illinois is already in negotiations to sell its lottery for a $15 billion lump sum and annual payments, and New Jersey in considering following suit. Other states are considering selling minority shares. And while government has often show little discipline here, private owners, of course, have no reason at all to discourage self-destructive gamblers. The highway back from Atlantic City features giant billboards for Gamblers Anonymous, a private group, but some of those shipwrecked by gambling will no doubt end up on welfare, so that the government receives with one hand what it pays out with the other.

There is another analogy with sports general managers, who like politicians have a limited stretch of time in which to prove the worth of their policies, and have every reason to favor plans that payoff while they're in office, not years later.

At the same time, government ownership and management of assets like roadways also fill, for better and worse, secondary roles like creating jobs with security and benefits for people willing to work who don't necessarily have the education and wherewithal to do well otherwise. That is why the turnpike employees are fighting hard against privatizing the roadway, while also pointing to homeland security, and the risks of having profit-oriented entities in control of assets vital to national security.

Mother Jones takes up the different motives of for-profit operations and compared to government in an article that raises questions about the role of Corzine's old firm, Goldman Sachs, in the Chicago skyway sale and the proposed Jersey sale. The firm has apparently been advising governments to privatize highways, helps them structure the deals to do so, and also invests in the new private assets, all of which can be seen as playing each sides against the other. They also have an impressive list of highway privatization proposals and projects.

On the other side of the coin, governments have proven they lack the will to impose rational road pricing; to use financial incentives and disincentives to maximize revenue and minimize traffic. After all, the people who benefit do so indirectly, while the people forced to pay new tolls resent it bitterly. And it's not just the Chicago Skyway and the Jersey Turnpike—Pennsylvania and Delaware are also looking at following Chicago's lead.

And not only do long term leases free governments to focus on core operations, it also generates cash in hand that can be invested to increase long term revenues. In New Jersey, for instance, Governor Corzine would use some of the lease money to help finance property tax cuts, which in turn should help the state's appeal and fiscal standing over time.

Airports are another natural asset to sell, and Chicago's Midway, once the nation's largest airport, may be the first to go private.

Meanwhile, cities like Detroit, which has resisted privatizing infrastructure under Mayor Kilpatrick (though it has contracted out services) risk falling even further behind. Then again, the same reasons for his resistance may mean that it would be a worse thing to entrust him with such a windfall.

Which brings us to the crux of the matter: the current privatizations may be only as worthwhile as what the money they generate is spent on, meaning that how well Daley, Corzine and others invest the new funds will go a ways to determining how far this wave goes, and how far it ought to.