Rocky Delgadillo was a long way from home, but not in unfamiliar territory, when he was spotted in Cambridge, Massachusetts, one Friday last October, wearing an overcoat and buying T-shirts at a Harvard University bookstore. The Los Angeles city attorney was attending alumni-association meetings at his alma mater and hoped to catch a football game the next day. He was accompanied by one of his top deputies.

Delgadillo seemed surprised to be recognized in Harvard Square as L.A.’s top lawyer, rather than as a former All-American football player — honorable mention, that is. He chatted easily about the Ivy League mystique, and about how he always thought they should let in more people of color. He grew more earnest when an L.A.-based reporter — who was as surprised as Delgadillo was at the chance meeting — reminded him of his pledge to beef up oversight of the Department of Water and Power, and asked if he was concerned about news reports pointing to fraud and waste at the troubled utility. He replied that a “forensic investigative” unit allowed him to be proactive in rooting out problems.

As Delgadillo fielded questions, sweat beads were forming on his deputy’s upper lip. The more Delgadillo spoke, the more sweat appeared on the deputy’s lip. Delgadillo was unfazed. “I’ll just keep turning over stones and deal with whatever crawls out,” he said cheerily. “That’s why they call me ‘Rocky.’ ”

The 45-year-old Delgadillo has used his name to invoke many images during an upstart political career and his current bid for state attorney general: Rocky the fighter, Rocky the underdog, Rocky the protector. But Rocky the digger? Such cheesiness, offered without embarrassment or irony, raised the questions that have hounded him since he was elected in 2001: Who is this guy? And who is helping him craft his image?

The city attorney wears many hats, advising some city officials, defending others, while prosecuting misdemeanors, gang injunctions and environmental crimes. In Delgadillo, law firms and corporations see a prudent legal counsel who knows when to turn to the private sector for help. His cadre of operatives, with its ties to the Democratic Party, Richard Riordan, Warren Christopher and the firm O’Melveny & Myers, sees him as the second coming. Local prosecutors question whether he is one of them, or whether he’s what some might call a “press-conference prosecutor.” Some unionized assistant city attorneys in what had become a decrepit public law office think he’s a creep with no regard for fairness or the law. Former top deputies insist that quality civil servants — adults who can accept adult decisions — respect him for trying to upgrade the office.

None of these perspectives resolves the various personal images he projects, leading to frequent speculation that he’s an empty suit, propped up by corporate clout and money and a personal story with holes in it. Is he a well-meaning cornball, one who exploits his name? Or is he — as a recent news story suggests — a shameless phony, a guy who fudges his résumé? Or is he a talented, hard-working guy who is not afraid to do the difficult things that might piss people off? If it’s the last, then how does such an inspiring figure, with a folkloric political rise and obvious personal charm, become so misunderstood? To answer that question, some legal and political observers have suggested it is time to look at the people Rocky has relied upon in his ascent.

The Delgadillo story is almost legend. His upbringing and résumé sound so promising: son of a JPL engineer who grows up in Highland Park, an athletic standout who sees violence in his community, a scholarship ride to Harvard, then Columbia Law School, and a stint as an entertainment lawyer at O’Melveny, where he catches the eye of Christopher, his mentor. He watches L.A. burn in the riots of 1992, and he decides to devote his life to public service. He becomes a deputy mayor under Riordan and is anointed as the Great Brown Hope with an Ivy League pedigree. He surprises former City Councilman Mike Feuer in the city attorney’s race in 2001, and all of a sudden, officials in City Hall, in an era of term limits, political paranoia and insecurity, have a comer to keep their eyes on.

But he works hard, is not afraid to toot his own horn and earns respect, at least in some halls of power. “Once you get close to Rocky, you see how diligent and hard-working he is,” says state Senator Gil Cedillo, who appreciates Delgadillo’s support for immigrant driver’s licenses and his involvement in homeless issues downtown. “He’s worked hard his whole life, and no one has given him anything. No one can challenge that about him. He has led an extraordinary life and is extraordinarily committed.”

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Delgadillo shakes up the City Attorney’s Office by bringing in top talent from big law firms and the U.S. Attorney’s Office. The move sparks rancor among rank-and-file attorneys who feel pushed aside and invites scorn over perceived favoritism. He develops a reputation as a novice beholden to Riordan operatives, such as former deputy mayors Ann D’Amato and Jennifer Krieger — a pair of savvy nonlawyers who serve as his closest advisers. Some are impressed with his desire to improve the office, though his administrative and personnel changes prompt assistant city attorneys to become part of a union. The cost of outside law firms — many of them his political contributors — rises sharply, but the costs of legal settlements decrease. He increases gang injunctions and develops a well-received neighborhood-prosecutor program.

“As an entertainment lawyer, he started with zero street credibility, though he accelerated the expansion of gang injunctions,” says a county prosecutor in the gang unit. “But he alienated civil servants, and he appeals more to corporate lawyers.” District Attorney Steve Cooley, who formed a County Prosecutors Association, which he claims Delgadillo has snubbed, and sponsored three-strikes legislation, which he says Delgadillo is avoiding, says, “I can’t say I know him. There’s some disengagement. He talks about abortion and the environment, that’s predictable. Set up a camera and he’ll be there. But he hasn’t impressed people that he has all the [skills] needed to be state attorney general. It’s not that he’s a Johnny-come-lately, more like a Johnny-come-early.”

To learn more about Rocky, one must look at his political operation and ask if it is helping or hurting him. Now that he is trailing Oakland Mayor Jerry Brown by 40 points, even Delgadillo’s fans are forced to admit that something has gone wrong. But is it Rocky’s fault? The pressure to get his mug on magazine covers led his office to go through more spokespersons than the fictional band Spinal Tap went through drummers. His campaign strategist, Larry Grisolano, quit on him, raising questions about who’s in charge. Both positions either report to, or inevitably have to deal with, D’Amato.

So, how much influence does D’Amato have? And is it a good thing? Lauded as a keen choice to be Delgadillo’s chief of staff in 2001, D’Amato, a City Hall veteran of more than 30 years who collects a full pension on top of a six-figure city contract salary, has been the older woman behind the promising young man, causing observers to wonder about some sort of “Mommy” complex. Some former employees say that perception is ludicrous. But many concede she is briefed on most, if not all, major decisions, and weighs in on legal matters despite having no legal experience. There also is a perception that she is overzealous in promoting Delgadillo, which may be confused with her own drive to be a political player, and that she lacks judgment and respect for the boundaries between politics and running a city office. The “Friends of Rocky,” as his inner circle is known, has another nickname, one that contrasts with the movie character Rocky, who waited a lifetime to get his shot at the big time: “Team 1600” is a reference to what many see as a pretentious and prematurely stated goal of the White House for Delgadillo someday. “It’s real, and it’s toxic,” says a former member of the office.

Delgadillo also has surrounded himself with Democratic Party operatives like Deputy City Attorney Kristina Scott, a low-key political consultant and former campaigner for Al Gore. Former members of his office say Team 1600 was enamored with former Deputy City Attorney Josh Perttula as much for his connections, particularly the Clintons, as for his legal prowess. Perttula, who now works for Ameriquest, would not return calls for comment. When he and other top-notch lawyers quit last year, rumors swirled that D’Amato and Krieger, a talented budget analyst with sharp elbows, had driven away quality people who valued the law over Delgadillo’s political future. But Terree Bowers, a former federal prosecutor now with Howrey, LLP; Luis Li, also a former assistant U.S. attorney, now with Munger Tolles & Olson; and Cecilia Estolano, a land-use lawyer recently tapped to run the Community Redevelopment Agency, are loath to validate such talk. Yet they are not eager to defend the environment they left. Li and Estolano declined to talk on the record for this story.

Privately, a number of current and former employees have acknowledged the questionable influence of D’Amato and Krieger. Some have rationalized it as a natural consequence of running a public law office. Bowers, who was hired to reform a shabby criminal-law section, and who has contributed to Delgadillo’s current campaign, avoids direct comment on the two, and chooses his words carefully:

“I consider Rocky a friend, though I am not a part of his inner circle. While a majority did good work, he inherited an office that lacked discipline. It is vastly improved. When he tried to upgrade the office, he met resistance. He also scared some other politicians with his ambition, and he developed some adversaries. Being the type to get out front on controversial issues, and not shy about holding press conferences, he ticked some people off. He served notice that he was not going to be pushed around in City Hall. Some people don’t like that.”

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Bowers and others concede the perception that loyalty to Delgadillo is rewarded more than it should be, but Bowers says, “Our mandate was to improve the office. Some of the special deputy positions created problems. But he hired some tremendously talented people who never would have given the City Attorney’s Office a second look in the past.”

One August day in 2004, Delgadillo appeared at a luncheon sponsored by the Los Angeles Chamber of Commerce. The L.A. Weekly had just published an exposé on the DWP and how, for close to a decade, the City Attorney’s Office had sanctioned confidential settlements of discrimination, harassment and retaliation lawsuits. The practice, considered illegal for public agencies, had emerged under Delgadillo’s predecessor, but for nine months his office resisted releasing the settlements, despite a threat of being sued under the California Public Records Act. Now that the cat was out of the bag, Delgadillo had decided to release the settlements, and he chose the well-attended luncheon to talk publicly about his commitment to openness and accountability.

Focusing on the public’s right to know what its government is up to, Delgadillo gave a stirring speech. “Can you imagine the Belmont school fiasco had people known?” he said. “Can you imagine Oracle, or Fleishman Hillard, being exposed were it not for lawsuits to recover millions lost? When the people are excluded, corruption and mismanagement win.” He hauled out the famous line by former Supreme Court Justice Louis Brandeis: “Sunshine is the greatest disinfectant of government!” Delgadillo went even further: “We cannot tolerate government conducted in backrooms with sweetheart deals.”

Afterward he announced the creation of a public-information unit, headed by Scott. Perttula, he said, would oversee the DWP, airport and harbor legal operations, which, according to a former spokesman, were “sinkholes of accountability.” He said his legal staff in those departments needed to remember that they work for the people of Los Angeles, not for the departments they advise. According to people who know him, Delgadillo fancies the example of Eliot Spitzer, New York’s indefatigable attorney general, who is as respected as he is feared. But Delgadillo’s performance in office shows him beneath such comparisons — not to mention his own words.

Delgadillo’s office will not say what he has done to improve accountability at the DWP or anywhere else. His office and campaign declined numerous requests to interview him. Despite two legal opinions by his own attorneys, he tolerates the secrecy of a pair of safety and training institutes at the DWP, funded with millions of ratepayer dollars but controlled by the International Brotherhood of Electrical Workers Local 18. Assistant City Attorney Fred Merkin was approached one day for his opinion on this arrangement, and he signaled his interest in talking about the issue, but said he had to clear it with the front office. A week later, Delgadillo spokesman Jonathan Diamond, a former editor of the L.A. Business Journal, told the Weekly that Merkin was no longer interested in talking.

Delgadillo ran up a half-million-dollar legal tab fighting a wrongful-termination lawsuit brought by a former investigator with the City Controller’s Office who nosed around a little too close to legal contracts on a major public-works case, and he refused to let Controller Laura Chick, once an ally and a political climber in her own right, audit his office’s use of outside firms. Legal costs have doubled in the last six years to more than $30 million. By the time the State Bureau of Audits got around to the job, auditors found insufficient documentation and failure to follow policies for oversight of private law firms that handle city business.

Despite all the fuss, his list of campaign contributors remains a who’s who of lawyers and firms. He claims outside firms have reduced settlement costs and increased verdicts for the city. Private firms argue that they work at a discounted rate for the city. Legal experts say the reduced rates are a red herring: High-profile government representation begets lucrative work in the private sector, not to mention the prestige of representing the city of Los Angeles.

When Delgadillo was a defendant in a wrongful-termination lawsuit by a former assistant city attorney, he advised the City Council not to convene a special independent committee to investigate the charges, despite a city ordinance that required it. Then he sealed his own deposition in the matter, which embroiled a group of Los Angeles judges, and the case had to be removed to Orange County. He hired criminal-defense attorney Carmen Trutanich, an old friend of D’Amato’s, as a special counsel on unrelated matters but allowed Trutanich to monitor outside lawyers handling the case, raising questions about a conflict of interest. City law prevents the City Attorney’s Office from representing itself in a lawsuit. The city got whacked with a $1.5 million jury verdict and stands to lose more than $5 million total when lawyers’ fees are counted.

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Perhaps the most disturbing aspect of Delgadillo’s administration is the fear of dissent or even open discussion among employees. A recent call to a veteran city attorney for some information on how the office operates certain charity funds elicited no information whatsoever, but this response: “You realize I am required to tell my supervisor about this call.” (The Weekly found at least one case in which Delgadillo violated his own office policy, by channeling settlement funds in a landfill nuisance case to a children’s charity, on which he has served as a board member.) A call to a member of the City Attorneys Association, an affiliate of the Service Employees Union Local 347, prompted this response: “We have to be very careful. Nobody is allowed to say anything. People are afraid if Rocky loses, then we’re stuck with him for three more years, and it’ll be hell for anyone who says anything.”

In an effort to look outside what many describe as a dispirited office, the Weekly called former O’Melveny partner Mark Steinberg, head of the Delgadillo transition team in 2001. Steinberg had been willing to spend time trying to shoot down a story on a group of ex-CIA spies who claimed to be investigating Delgadillo’s use of private attorneys, but he, like many others, refused to talk substance. “I have said what I am going to say, which is nothing,” he said. Steinberg later left a voice message in which he explained, “I want to see Rocky elected, and I don’t want anything to jeopardize that.”

In recent weeks, Delgadillo has put out a barrage of press releases. Public lawyers like to say that the beauty of their job is they never have to fudge facts or put a false shine on anything. But Delgadillo has had to live down troubling disclosures. The L.A. Times reported his receipt of campaign contributions from landlords after reducing their settlements in a lawsuit over slum conditions; his decision not to prosecute a billboard company, which contributed $125,000 to him in 2001, for vandalism, after investigators failed to interview key witnesses; and overblown claims about his academic and sports credentials. The Weekly reported on a repeat sex offender who went free on Delgadillo’s watch, and who trolled MySpace.com, later to be convicted (by the D.A.) of molestation.

Yet it is rare that Delgadillo himself — the husband, the father, the lawyer or the public advocate — is described in negative terms. “He’s a very intelligent, creative and caring guy,” says a former top attorney in his office, who, at this late stage in the game, is among those who cannot bring themselves to be named, or to openly stand up in defense of Rocky. Maybe that says more about his people than about him. Observers might wonder how Delgadillo, by most accounts a decent human being who has made a mark on the city in a short time, could alienate so many groups — prosecutors, his own employees, political peers — and attract so much unfavorable attention.

No one will likely say for sure who thrust what upon Rocky, or whether his own instincts should be questioned. Team 1600 has an office to run, and an election to focus on. But if the advance polls are right, Delgadillo could be coming right back to what he says he loves, representing the city and protecting its citizens. Either way, he will have a chance to project a less complicated and compromised image, one that doesn’t prevent him from being widely accepted as all he’s supposed to be.

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