We haven’t heard much from Maureen O’Connor over the past few years, and now we know why: The former mayor was developing a mammoth gambling habit and, prosecutors say, pilfering from her late husband’s charitable foundation.

O’Connor joins a long list of San Diego mayors who are remembered for their resignations, indictments, questionable connections and inappropriate behavior. Not to mention a jail term or two.

Who’s the most notorious of all? Leaving out O’Connor, whose scandal has yet to fully unfold, here’s a ranking of the eight most scandalous San Diego mayors.

1. Rutherford B. Irones (1934-1935): The Hit-and-Run Mayor

Irones cracked up his career when he went out for a drunken spin in a city-provided Lincoln sedan that the press dubbed his “royal coach.”

He crashed into a sailor’s car on Reynard Drive in Mission Hills and promptly fled the scene, leaving the sailor’s wife injured. The district attorney later charged that Irones, a physician, failed “to stop and assist, comfort or even sympathize with that little lady lying there with a broken back.”

A cover-up briefly hid the news of the mayor’s hit-and-run, but the real story leaked out. He resigned, was found guilty and received a six-month jail sentence.

In the ultimate insult, his death in 1948 only merited a few paragraphs in the San Diego Union.

For more about the mayoral crack-up, check our history flashback here.

2. Dick Murphy (2000-2005): ‘Judge Mayor’ Throws Himself Out

A former judge, Murphy was another in a long line of mild-mannered moderate Republicans to hold the mayor’s office. Accusations of financial mismanagement, corruption and fraud at City Hall tainted his terms, punctuated by a Time magazine article that called him one of America’s three worst big-city mayors.

He resigned abruptly, saying, “It’s clear to me that the city needs a fresh start.” But he has since tried to repair his reputation and wrote a book in 2011 that offered his 10 “thought-provoking proposals for the future of the city.”

3. Roger Hedgecock (1983-1986): Tried, Convicted and Expunged

Hedgecock, elected as a county supervisor in his early 30s and a mayor at 36, skittered into a complicated legal morass as he was accused and convicted of felony conspiracy and perjury counts. Most of the accusations revolved around charges that he accepted illegal donations and covered them up.

He resigned from office but ultimately cleared his name when a court threw out most of the charges. The remaining charge was reduced to a misdemeanor and ultimately expunged.

What happened? Only years later was it revealed that a bailiff who believed in Hedgecock’s guilt engaged in misconduct: He “plied jurors with liquor. He reminded them that it was expensive to keep them secluded, so costly that they were expected to ‘do a good job.’ And, against all rules, he partied with the jurors and told them stories suggesting that other juries had let minor issues keep them from a verdict,” according to the Los Angeles Times.

Hedgecock became a conservative radio talk-show host (he said the job paid more and required less work than politics) and is still one today.

4. Frank E. Curran (1963-1971): He Caught a Cab Scandal

As the Los Angeles Times put it when he died, Frank Curran “saw his career blessed by the city’s growth but ultimately cursed by a wide-ranging bribery scandal.”

While he was acquitted of taking bribes from a cab company in return for hiking taxi rates, he was unable to restore his reputation.

His replacement? A young upstart named Pete Wilson, who became a senator, a governor and a presidential candidate.

5. William “Bill” E. Cleator Sr.: (1983-1983): That’s No Way to Treat a (Royal) Lady

Cleator tried to guide Queen Elizabeth II out of a reception during a royal visit and accidentally touched the monarch. This did not go over well considering the royal no-touch policy.

“The British media described the gesture as an insult — a commoner daring to touch royalty — and said the gentle brush caused a look of annoyance to cross the queen’s face,” the AP reported upon Cleator’s death. “‘Get Your Hands Off Our Queen,’ a headline in one British tabloid screamed. Television stations replayed the incident in slow motion.”

6. Louis Wilde (1917-1921): His “Jazz Cat Gamble” Wasn’t Purr-Fect

Never mind that he’d been accused (and exonerated) of embezzlement. While serving as mayor, Wilde wooed investors into a San Diego oil-drilling scheme that he called a “Jazz Cat Gamble”: “your $100 gamble could be worth upwards to $20,000,” according to a 2009 U-T article.

Skeptics, including a local newspaper, pounced. The ever-quotable Wilde responded with a libel suit and a plea to his investors: “I want friends who have some dynamite and stick-to-it-ive-ness and less skim milk.”

Wilde ultimately withdrew the lawsuit. As the U-T put it: “His drillings had all come up empty and his patient investors lost everything in his Community Oil fund, which ended up as dry as the oil wells.” Wilde wouldn’t serve another term.

7. Michael J. Zucchet (2005-2005): The Three-Day Mayor

Zucchet served as acting mayor for just three days in 2005 after Murphy’s resignation before he stepped down upon his conviction for corruption in the “strippergate” scandal. He was ultimately exonerated, however, and is now the head of the city’s white-collar labor union.

8. Susan Golding (1993-2000): Spousal Sorrow Didn’t Stop Her

Golding’s husband, Richard Silberman, was a major player in San Diego’s halls of power: “He bought and sold banks, chaired the downtown redevelopment agency and helped found Old Town’s Bazaar del Mundo,” San Diego Magazine reported. “But in 1989, Silberman was busted in an FBI sting for laundering $300,000 in what he believed was Colombian drug money.”

Golding divorced Silberman, who went to federal prison. She shrugged off the scandal, and so did voters: They subsequently elected her mayor for two terms.

Dishonorable mentions:

John L. Sehon, as we reported in a history flashback, forcibly occupied City Hall on the morning of his inauguration in 1905. William “Billy” Carlson, who’s still San Diego’s youngest elected mayor (he was 28 when he took the job in 1893) landed in prison after serving his term. Joshua Bean, the brother of famous Judge Roy Bean, faced allegations that he took bribes in 1850 after he presided over the shoddy construction of a jail. And George Tebbetts, who served in 1852, reportedly took part in the lynching of men who stole his horse.

Randy Dotinga is a freelance contributor to Voice of San Diego. You may not republish this content without his consent. Please contact him directly at randydotinga@gmail.com and follow him on Twitter: twitter.com/rdotinga.

Disclosure: Voice of San Diego members and supporters may be mentioned or have a stake in the stories we cover. For a complete list of our contributors, click here.

Randy Dotinga

Randy Dotinga is a freelance contributor to Voice of San Diego. Please contact him directly at randydotinga@gmail.com...

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