Councilman Michael Gregory, David Anderson
What a difference a year makes for Gregory. Last year, the sharp-dressed, well-groomed councilman had more than a few hairs out of place. Under his watch, there was a strong possibility of losing San Leandro Hospital, which sits in his district. He was also on the outs with local labor unions, which insiders say caused him more than a few night’s sleep. Fast forward and the political landscape looks far more rosy for Gregory. San Leandro Hospital’s future is not secure, but the bleeding has been stopped for time being and labor support has even come his way. Gregory is simple: he is all about improving lifestyle. He promotes ditching the car for a bike and eating your vegetables. He’s congenial and well-liked, either because he smiles a lot or does not aim to make waves. His opponent, though, comes to San Leandro with quite a bit of baggage. David Anderson is not well-known. What he is known for is accusations of wrongdoing at the school district in Oakland. Anderson, though, is a strong union man, which made Gregory nervous. In the end, the labor unions, seemed to have shied away from Anderson in favor of Gregory. It will be interesting exactly how Anderson tacks against Gregory sunshiny persona and whether he has sounds like he has the experience to match the incumbent. If you are looking for political fisticuffs this is probably not the race for you.
School Trustee Pauline Cutter, Corina Lopez
With two months to go, this is the race most likely to produce a surprise. Four years ago, Ursula Reed played this role. This time around it could be the Princeton-educated Lopez who pulls it off. District 5 has not seen a competitive council race in over a decade. Councilman Bill Stephens was re-elected twice without an opponent. Lopez is well-spoken and intelligent, but her main asset could be her grasp of the undervalued and unrepresentative Latino demographic. She is also a ballroom dancer, which should go well with the Dancing with the Stars set. In a city with a burgeoning Latino flavor, neither the city council or school board is represented by a person of Hispanic descent. If she can connect to those voters, she could defeat the more experience Pauline Cutter. Rallying that large sleeping giant of a demographic, though, is a big if. Cutter has shown herself to be a part of the more moderate wing of the school board. For instance, she sided against giving departed superintendent a pink slip earlier this year in opposition to the Katzites who had it in for Christine Lim. Some though say she has done little to set herself apart from a quite lackluster school board. While she has a good deal of union support, it is a bit spotty and her support among the current school board members is waning. This summer she seemed fearful of losing Tony Santos’ support which is only exacerbated by Santos acolyte Charles Gilcrest being involved in Lopez’s campaign. Cutter is a bit laid back in demeanor and will likely step up the rhetoric making this race a tossup and with any close race, it usually comes down to who makes the biggest mistake and when.
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