New Orleans 2020. New Orleans was a gigantic clusterfuck even before it was destroyed by Hurricane Katrina. That said, it has two big advantages: first, it’s the major port in and out of the Midwest. Second, it has a famous if underperforming mass transit system. A few short streetcar extensions and a modernized network would work wonders. (NOLA cars stop every two blocks and run at 10 miles an hour.)
