San Jose Mayor Chuck Reed has a dubious history when it comes to endorsements. In years past, Reed has given his blessing to a number of individuals who went on to lose. Don Gage is hoping to avoid that same fate as he begins his Gilroy mayoral campaign in earnest with Reed’s support.

The city’s fearless and occasionally politically tone-deaf leader, Chuck Reed, was riding high after successfully placing pension reform and binding arbitration on the ballot with a carefully stitched-together coalition that seemed to spell the end of organized labor’s control of the San Jose City Council.

The afterglow was short-lived, however. Reed threw the new majority into chaos with his divisive endorsement of gay marriage opponent Larry Pegram for a council seat, just a day before a California court overturned Prop 8.

Fresh off what may have been the biggest victory of his political career, Mayor Chuck Reed last week decided to immediately blow some of his hard-earned political capital, endorsing the conservative Christian council candidate Larry Pegram.

Unless Fly is missing something, the timing of the mayor’s announcement couldn’t have been worse. In recent years, Pegram has been San Jose’s most high-profile anti-gay activist. He campaigned locally for the ban on gay marriage, without success.

With all the problems he’s had with Rob Davis, police auditors and police-community relations during his term, the last thing San Jose Mayor Chuck Reed would seem to be equipped to do is weigh in on the management of another law enforcement agency. But that’s exactly what he did this week. Reed has endorsed long-shot Sheriff candidate Richard Calderon, becoming the first mayor anyone can remember to endorse the challenger to a sitting sheriff. Which has left everyone scratching their heads.