When Detroit filed for the largest municipal bankruptcy in U.S. history on July 19, it served as stark evidence that the regional economy has yet to recover from the Great Recession.

The city's continuing troubles have hammered law firms heavily dependent on automakers for corporate work and employment litigation. Even as a streamlined General Motors Co. and Chrysler Group LLC, which both filed for bankruptcy in 2009, have returned to profitability, Detroit-area law firms — especially big ones — are still coping with a busted real estate market and its ripple effects. At the same time, they are trying to serve cash-strapped clients that demand more value from their law firms.