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— It's been seven and a half years since Bill Kolender, backed by almost every member of San Diego's downtown establishment, demolished Sheriff Jim Roache's reelection hopes. Four years earlier, Roache had defeated John Duffy's hand-picked candidate, Assistant Sheriff Jack Drown, now Kolender's second in command. Duffy, the controversial incumbent, facing a raft of public spending scandals, had decided not to run again.

Rooted in East County conservative politics, Roache was always regarded with suspicion by the editorial power brokers at the Union-Tribune. He turned out to be a miserable practitioner of the art of spin, schmooze, and payback so vital to success in the cozy worlds of La Jolla and Rancho Santa Fe.

When Roache came up for reelection in June 1994, his enemies were waiting for him with Bill Kolender, a representative of San Diego's easygoing insider politics. A local boy whose father ran a jewelry store on lower Broadway, Kolender joined the San Diego Police Department in 1956. During the 1960s' turmoil, Kolender's role as a community-relations officer allowed him to rise quickly through the ranks. He began to rub shoulders with the new Republican political establishment led by the city's ambitious mayor, Pete Wilson, and fortified by Helen Copley, who had inherited the Union-Tribune from her old-school Republican husband, Jim Copley.

In 1975, Pete Wilson picked Kolender to succeed police chief Ray Hoobler. After 13 years, Kolender stepped down in August 1988 to become assistant general manager at the Union-Tribune. The move followed by two years a 1986 ticket-fixing scandal, first reported by the Los Angeles Times, involving members of the Chargers, for which Kolender was reprimanded by the city manager. A series of racially tinged police shootings in 1987, combined with a lingering mystery about the 1985 slaying of prostitute and police informant Donna Gentile, added to the controversy surrounding the departing police chief.

In 1989 the county grand jury would link Kolender to Mission Valley madam Karen Wilkening, which both he and Wilkening later denied.

The undistinguished nature of Kolender's tenure at the Union-Tribune led many to conclude that he was there to keep tabs on publisher Helen Copley's son David, who had been arrested for drunk driving in 1986 and again in South Mission Beach in December 1989.

In 1989, Kolender became the target of the Newspaper Guild, then fighting for the survival of its union's local at the Union-Tribune. Union supporters handed out leaflets at the Solana Beach synagogue where Kolender was being feted at a testimonial dinner.

The Los Angeles Times reported that in December 1989, as a midnight strike deadline approached, Kolender positioned himself at the employee exit turnstile of the newspaper and checked to see if anyone was making off with company property. He reportedly confiscated a Rolodex belonging to reporter Joe Gandelman, who said the address-card index belonged to him; Kolender told a television station he thought it had been purchased with U-T funds. The incident led Newspaper Guild president Ed Jahn to tell a rally of supporters that the ex-chief was "behaving like a Kmart security guard."

The Los Angeles Times also reported in 1989 that Kolender had written a letter in support of a pardon for Dominic "Bud" Alessio, who served time on a federal felony rap. Alessio had lavished gifts on a prison official who gave preferential treatment to his father John and uncle Angelo, in prison at the time for income-tax evasion. John Alessio was a protégé of fallen financier C. Arnholt Smith; he also once operated the Caliente racetrack and sports book in Tijuana.

"Bud was a victim of circumstances and did what any son would do for his father," Kolender wrote in a letter uncovered by the Times using the federal Freedom of Information Act. The Times story pointed out that federal organized-crime prosecutors "considered the case far more serious. They contended that prison officials were bribed with food, lodging, and entertainment gifts in return for allowing John and Angelo Alessio to conduct secret rendezvous with women friends. In all, six people were convicted or pleaded guilty in the case."

In an interview with the Times, Kolender further explained his position. "I think that, under the circumstances he deserves a pardon. He's contributed to his community. He's served his time. He did something for his father, he made a mistake, and he paid for it."

In 1991, Kolender's old friend, then-governor Pete Wilson, took Kolender away from his duties for Helen Copley when he put him in charge of the California Youth Authority. In 1992, the Los Angeles Times folded its San Diego edition, which had done such a thorough job of chronicling the ex-chief's history. Kolender remained at CYA until he ran for sheriff in 1994. In a big-money campaign run by political consultant Tom Shepard, who had earlier pled guilty to charges brought in connection with the Roger Hedgecock political money-laundering scandal, Kolender prevailed against the incumbent Roache. He was reelected with no opposition in 1998.

Kolender's second bid for reelection this coming March seems destined to go smoothly. Though Kolender has his foes, who cite a list of unsolved homicides and other maladies they claim beset the sheriff's department, they admit the demise of the Los Angeles Times in San Diego gave Kolender a free ride in the surviving media -- especially at the Union-Tribune, which never seemed anxious to take on a family friend.

Recent campaign-contribution reports show that as of October 10, Kolender has raised $81,475. Union-Tribune publisher David Copley gave $500. Members of the Alessio family who each gave $500 include Frank, Virginia, Linda, Katherine, and Dominic. And Robert DePhilippis, owner of the Butcher Shop restaurant in Kearny Mesa as well as the Filippi's Pizza Grotto chain, gave $600. Craig Ghio, owner of Anthony's Restaurant, gave $100.

John Dahlen, co-owner of Kolender's old watering hole, Bully's East on Camino del Rio South in Mission Valley, kicked in $500. Dahlen is also connected with the Old Town Mexican Café, another Kolender hot spot. According to local legend, it was at Bully's that Kolender met his present wife, Lois Karas, whose husband, ex-Charger Emil Karas, died of cancer in 1974. Kolender, his old sidekick Ron Reina (who later became his official spokesman at the sheriff's department), a host of other cronies, and various members of the local sporting establishment, including boxers and football players, held their fabled revels at Bully's.

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