Delgadillo is a native of Highland Park, Los Angeles. He attended Harvard College, where he won the Robert F. Kennedy Award given each year to a member of the varsity football team. He went on to Columbia Law School, graduating in 1986. He passed the California State Bar in 1986. After a short period in private practice at the prestigious Los Angeles law firm O'Melveny & Meyers, he joined Rebuild LA, a non-profit formed in the wake of the 1992 riots in Los Angeles. He later joined the administration of Mayor Richard Riordan, eventually becoming deputy mayor for economic development. He ran against former Governor and Oakland Mayor Jerry Brown in the 2006 race for the Democratic nomination for state Attorney General of California.
City Attorney
As City Attorney, he has subscribed to the "broken windows" theory of law enforcement. Among the programs Delgadillo has implemented is a neighborhood prosecutor program that put city attorneys in each of the city's police divisions. He has also sped up the implementation of civil gang injunctions, which largely limit association by gang members in certain defined areas. Civil rights groups have challenged the injunctions, but the state's courts have upheld them. They have come under renewed attention recently, particularly in South Los Angeles, where some community members have complained that it is difficult for gang members to escape a sometimes intrusive law enforcement structure. One of the most well-publicized prosecutions by Delgadillo's office was that of entertainer Paul Reubens, more commonly known as Pee Wee Herman, for possession of child pornography. Delgadillo's office arranged a plea bargain requiring Reubens to pay a $100 fine and serve three years of probation. Delgadillo was criticized, for recommending to the Los Angeles City Council that the City pay $2.7 million to black firefighter Tennie Pierce, who alleged he was fed dog food as a firehouse prank and later retaliated against by his fellow firefighters when he complained to superiors. Delgadillo argued that the City would likely have been forced to pay even more money to Pierce had the case gone to trial, in addition to legal costs, considering jury verdicts in past cases of a similar nature. According to the Los Angeles Times, in September 2007 the City of Los Angeles agreed to pay Pierce $1.49 million to avoid going to trial, with the support of then-Mayor Antonio Villaraigosa, who had vetoed the earlier $2.7 million settlement offer proposed by Delgadillo, and the City Council. With legal costs to the City reaching an estimated $1.35 million, the taxpayers ended up having to pay out $2.84 million in the Pierce matter. An agreement facilitating digital billboards in Los Angeles while he was seeking campaign funds from the industry created controversy as to possible bias in agreeing to the advertising expansion.
