[citation needed] Aguirre worked as Assistant U.S. Attorney for the Department of Justice and directed a grand jury investigation of pension racketeering.

In 1990, Aguirre allied with the Chicano Movement to file a successful federal voting rights lawsuit to overturn San Diego’s redistricting.

In 1993, Aguirre successfully defended the United Farm Workers Union in Yuma, Arizona, in a case with lettuce grower Bruce Church.

Aguirre ran for San Diego City Attorney in 2004, in the midst of a financial crisis and investigations by the Securities and Exchange Commission.

The resulting deficit of some $1.4 billion left the city’s finances in shambles and made it virtually impossible to issue municipal bonds.

[citation needed] Aguirre ran as a "clean up the mess" outsider, with support from Democrats in the officially nonpartisan race, and won with 50.4% of the vote.

[3] A 2008 Wall Street Journal article praised Aguirre’s efforts to address the City of San Diego's hundreds of millions of dollars of unfunded pension liabilities.

[6] As City Attorney, Aguirre filed a legal action to force a developer to reduce the height of an already constructed office building near an airport.