ELECTION ’12//SAN LEANDRO CITY COUNCIL//ANALYSIS | Nearly two years to the day members of Stephen Cassidy’s political team were caught distributing campaign literature at San Leandro school events, one of his preferred candidates for the city council is attempting to the navigate the grey area between violating election law and shrewd politicking this year.

Cassidy takes a bath in 2010

Numerous witnesses say volunteers for the council campaign of San Leandro school board president Morgan Mack-Rose offered them literature in support of the school district proposed parcel tax, Measure L. However, the flyer also included a separate, full-color mailer for Mack-Rose.

One volunteer passing out literature last Thursday night at Roosevelt Elementary’s “Back to School Night” is the same person who during the 2010 mayoral race drew the ire of Cassidy’s opponents when she was found to be passing literature on the grounds of San Leandro High School at a similar event. This time around no witnesses reported the volunteer, identified as the spouse of the Mack-Rose’s campaign manager, Tim Holmes, only passed out the flyers on the sidewalk and away from school property.

Nevertheless, the incident again raises questions about the propensity of Cassidy and his circle of political allies for pushing the bounds of fair play along with an ease for bending the rules to their personal advantage.

Along with Mack-Rose, who Cassidy backed to replace him on the school board in 2008, the gruff mayor is also endorsing District 4 candidate Chris Crow and another former minion from the school board, Hermy Almonte in District 6. However, the trio have gone to great pains to downplay their association to Cassidy and his growing unpopularity.

The use of school district functions to promote the campaigns of Mack-Rose, Cassidy and another loyal acolyte, school board member Mike Katz, is not surprising since the group’s only real political power in San Leandro is derived from the sphere of its schools. In 2010, both Cassidy and Katz were accused of using another event at Roosevelt Elementary, clad in campaign t-shirts, ready to be dunked for charity. Opponents cried foul, but a complaint to the FPPC went nowhere.

Over the past few weeks, Mack-Rose’s campaign has been aggressive in attacking District 2 incumbent Councilwoman Ursula Reed with a mailer targeted for seniors insinuating she urged the city to buy expensive iPads ostensibly for her own use and entertainment. In an election season in the East bay bound to be vicious, the assertion, later debunked by city staff who say Reed did not receive an iPad, likely stands as the biggest political lie, so far, this fall.