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The Men Least Likely: A Brief Survey of S.F.'s Worst Mayors 

Wednesday, Nov 9 2011

Ever since Ed Lee referred to PG&E as "a great company that gets it" during a press-friendly event featuring kiddies, baseball, and the company that blew up an adjacent town, it's been clear our mayor is not exactly a modern-day Cicero.

And yet it was difficult to ignore the odd manner in which Lee thanked Lt. Gov. Gavin Newsom — remember him? — after the latter threw in for Lee's mayoral campaign. The endorsement means an awful lot, Lee noted, as Newsom is "one of our City's most successful former mayors."

Other than removing himself from the city with haste befitting a man fleeing a nuclear test site, it's difficult to quantify just what Newsom accomplished that warrants elevation to Lee's pantheon. Sure, he's lieutenant governor, but three former city mayors have gone on to be governors, two have been senators, and one managed to land his own Chronicle column.

Still, if there's a listing of our most successful former mayors, it stands to follow we can rate our least successful ones as well. Sadly, it's not that exclusive a club:

• Stephen Webb followed his tenure as mayor of San Francisco in 1855 by serving as mayor of Salem, Mass. Leading our city didn't seem to do much for Webb's upward mobility, as he was also mayor of Salem before heading west.

•If ever there was an anti-Newsom, it was George J. Whelan, the only mayor of San Francisco of whom no surviving portrait or photo exists. We know he served for six months in 1856, but no one knows when he was born or when he died. A ship named the George J. Whelan, however, sank in Lake Erie in 1930, killing 15 men. You can find photos of the boat.

•Speaking of ships, former mayor Andrew Jackson Bryant died in 1888 after allegedly throwing himself from a bay ferry in an apparent suicide.

• James Phelan (mayor from 1897 to 1902) went on to high honors — he served in the U.S. Senate and has a street named after him. Retrospectively, however, his "success" is more than a bit embarrassing. One of Phelan's key campaign issues for his senate seat was a drive to "Keep California White."

• George Boxton lasted only a week as mayor in 1907. Appointed after his predecessor, Eugene Schmitz, was convicted of corruption, it was quickly revealed that Boxton, too, was on the take. He lived out his days pursuing his chosen profession, dentistry, and apparently did not deign to give subsequent political endorsements.

About The Author

Joe Eskenazi

Joe Eskenazi

Joe Eskenazi was born in San Francisco, raised in the Bay Area, and attended U.C. Berkeley. He never left. "Your humble narrator" was a staff writer and columnist for SF Weekly from 2007 to 2015. He resides in the Excelsior with his wife, 4.3 miles from his birthplace and 5,474 from hers.


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