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This hasn't been the best year for Casey Gwinn, San Diego's city attorney. The 41-year-old graduate of UCLA law school, who was elected in 1996 and reelected four years later with no opposition, began 2001 scrambling to explain why the city had lost a $94.5 million inverse-condemnation lawsuit brought by Otay Mesa developer Roque de la Fuente. The news didn't get much better last month when an Orange County judge upheld most of the damage award, leaving local taxpayers facing a judgment that could be as much as $100 million or more -- a sum that includes interest and attorneys' fees. Years of appeals may lie ahead. Gwinn faced much criticism about his office's conduct of the trial, in which he failed to cross-examine De la Fuente on the witness stand and watched as one of the city's top expert witnesses was discredited by the plaintiff's attorneys. After the disastrous verdict, Gwinn surrendered the case to outside counsel, the big Los Angeles law firm of Latham & Watkins.

But even that move proved embarrassing, when it came to light that the city had forked over at least $3 million to the Los Angeles firm for coming up with the failed appeals strategy.

Then there is Gwinn's attempt to win the coveted appointment by the administration of President George W. Bush to become San Diego's next United States attorney. A loyal Republican who collected the endorsements of three GOP congressmen (Randy "Duke" Cunningham, Duncan Hunter, and Darrell Issa), Gwinn, on the surface at least, seemed like a shoo-in. But the White House has been dragging its feet on filling the post, and last month, the San Diego Union-Tribune made it clear that Gwinn was not the newspaper's choice, proclaiming instead, "The best candidate in this field of applicants is Charles La Bella," an ex-deputy U.S. attorney who earned fame as a Clinton antagonist.

Asked why the Union-Tribune failed to support Gwinn, insiders cite the opinion held by many local lawyers and politicos: the city attorney is an intellectual and political lightweight who got into office through the good graces of his onetime boss, ex-city attorney John Witt. Insiders also say that Gwinn has often seemed too willing to cut ethical corners. On the verge of retirement back in 1996, Witt delayed announcing his departure, hoping that it would be too late for candidates other than Gwinn to get into the race to succeed him.

The strategy worked and Gwinn ran unopposed. Even then, he raised thousands of dollars from members of law firms with business before the city, including the downtown firm of Luce, Forward, whose partner, Charles Bird, a Gwinn contributor, represented the city in its legal battles against opponents of the Chargers' ticket guarantee and the downtown baseball stadium. Much of the money was used to repay Gwinn for a personal loan he had made to an earlier campaign in which he had run for district attorney.

Thus assured of winning office, during the months before the March 1996 election, Gwinn began lashing out at opponents of the Chargers' ticket guarantee and the Qualcomm Stadium expansion. In January and February of 1996 he came up with a series of legal actions on behalf of the ticket guarantee and expansion plan, which requires city taxpayers to pick up the tab for unsold seats during Chargers games at Qualcomm Stadium. The long-running legal battle lasted until February 1997, when Gwinn, who by then had been elected city attorney, convinced superior court judge Anthony Joseph to throw out a taxpayer lawsuit challenging the Chargers' deal with the city.

"It was a clean sweep for the city," Gwinn boasted to reporters outside the court. "The judge has made clear that what the city is doing at the stadium is legal and appropriate -- and has been." The ticket guarantee has since cost city taxpayers more than $10 million, and the clock is still running.

Gwinn has been equally stalwart in his backing of the new downtown baseball stadium. Critics say his oft-times emotional support of the project has sometimes gotten in the way of his duties as city prosecutor. They point to the case of Padres owner John Moores and Councilwoman Valerie Stallings, who was eventually forced to plead guilty to charges of political corruption and resign when it came to light she had received stock tips and other favors from Moores.

Even well before the Stallings transgressions emerged into public view in April 2000, it was apparent that Gwinn was consistently an ally of Padres management.

After Moores brought his November 1998 campaign for the downtown baseball stadium to a victorious close, Moores rewarded many of his supporters, both in and outside city hall, with a series of personal gifts. One recipient was city planning commissioner Geralda "Gerri" Stryker, who had been a co-chairman of the pro-stadium campaign, on which Moores had spent more than $1 million. The Moores gifts to Stryker included a "Two-Volume Book on Lane Field," a "Commemorative Wine Bottle," and a "'98 Player Photo Album," according to her financial disclosure statement.

Though the gifts were never appraised, other officials who had received them reported their value to be in excess of $300. One nongovernmental official who received the photo album proudly told friends that as a collectors' item it was worth "thousands of dollars." If so, then Stryker, under state conflict-of-interest laws, would have been barred from voting as a planning commissioner on any and all aspects of the downtown stadium and related development, including hotels and office buildings.

Gwinn's office, however, quickly issued an opinion clearing the way for Stryker to participate in all stadium-related votes that came before her. "If the fair-market value [of the gifts] is difficult to ascertain," Gwinn's office opined in a letter dated December 29, 1999, "then the value is to be determined by the cost of the donor. If this value is unknown, then the recipient shall make a good faith and reasonable approximation [of the gifts' value].

"Based on our investigation, we do not have credible evidence establishing that Ms. Stryker's valuations of the three gifts were not a reasonable approximation. By law, she therefore lacks a financial interest in [the ballpark project] because she has not been the recipient of gifts in excess of $300 from any donor, specifically Mr. Moores."

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