After reading it you may not agree with everything he says but you will understand the fundamental issues that are at stake. He argues that it is inherently risky to effectively 'lock in' one particular policy arrangement for a significant part of the urban public realm for 75 years!
Now he has followed up with a critique of the very similar contract in Indianapolis that soon goes to its city council for approval. He sees the Indy deal as even worse than Chicago's.
For those in a hurry, here are some key quotes from the Urbanophile's discussion of the Chicago deal:
... even if Chicago didn’t extract the last penny of value out of the parking meters, so what? It’s highly unlikely you are going to win huge in every deal. In fact, the more of them you do – and Chicago has done several – the more likely you’ll encounter a loser...The Urbanophile is even more scathing of the Indianapolis contract (as currently written). Go take a look.
I’ve long said that most of the critiques of the Chicago parking meter lease are overblown... But even so, this deal, and any deal like it, contains serious fatal flaws.
The main problem with the parking meter lease is that it locks the city into a particular policy structure on parking for the next 75 years. In order to get someone to pay $1 billion up front, you have to give them certainty as to the quantity, location, hours, and rates of the meters. All of these matters are thus written into the contract. In effect, Chicago has irrevocably set public policy with regards to parking for the next 75 years.
This might not matter for something like a toll road ...
But with on street parking it is very, very different. Parking spots are the curb lane of your streets. Your streets are the primary public space in your city. They are intimately connected with everything that happens in the city, which is one reason parking policy is so politically controversial. ... The city of Chicago has ceded a portion of its urban planning powers to a private company. ...
The other tragedy is that Chicago has locked itself into a parking policy at just the moment that we’re on the cusp of a revolution in on-street parking management. ... dynamic congestion pricing is coming to parking. ...
We have no idea what the world is going to be like 5, 10, 25 years down the road, much less 50 or 75. Anything that locks cities into a particular policy framework for the long term for areas where there isn’t a strong track record of success poses a high risk. I would strongly advocate that cities avoid entering into long term on-street parking leases until successful models have been developed and have proven themselves through shorter term, successful contracts.