Cleveland the answer
With an $805 million shortfall in retiree funding for health care, Chicago Mayor Rahm Emanuel announced, starting Jan. 1 with a three-year phase-out, he is going to dump the retirees into the federally run health insurance exchanges, i.e. the Affordable Care Act. The federal government and individual retirees will pick up the tab for health care, relieving the city of Chicago of its burdensome obligation to its retirees.
More local governments, cities and states will follow suit. As only Washington can print money to pay bills, we will need to print larger denominations. Currently, the $100 bill is the largest denomination printed today. By the way, it is the most printed denomination of U.S. currency.
Even though last printed in 1934, plates for the $500 bill and $1,000 bill will need to be dusted off and inserted into the printing presses. I have to say "show me the Clevelands" or the "McKinleys" has a nice ring, like the obsolete "Benjamins."