He was the federal court appointed attorney that represented 170-plus municipal entities with investments of over $5 billion in the Orange County, California Chapter 9 bankruptcy. On December 6, 1994, the County of Orange declared Chapter 9 bankruptcy, from which it emerged in June 1995. The Orange County bankruptcy was the largest municipal bankruptcy in U.S. history. Following a tumultuous several year period of financial disclosures by the City of San Diego relating to its massively underfunded pension and retiree health care system, in 2005 Shea ran for Mayor of San Diego on a platform of filing a Chapter 9 bankruptcy for the city in order to restructure its troubled financial condition.