‘Tis the season for people to ponder making a political run, and a newcomer to the scene intends to shake up San Jose’s City Council. Fly has learned that Tam Truong, a 30-year-old detective for the San Jose Police Department, picked up filing papers from the City Clerk’s office this week and plans to challenge District 4 Councilmember Kansen Chu in the fall. What makes Truong such an intriguing candidate, aside from being young and well educated, is who he intends to align himself with.

The winter of discontent continues unabated for the Milpitas Monarch, Jose Esteves, who complained at last week’s City Council meeting of feeling harassed by Public Records Act requests. (Message to Mayor Esteves: If you already feel harassed, stop reading here.) It would be one thing if the PRA requests were coming from an angry citizen, but almost half of the 66 requests—which ask for phone records, emails, video surveillance, and dates and times the mayor used a key card to enter City Hall—came from Councilmember Debbie Giordano. It turns out the mayor, whom critics accuse of holding an unauthorized wedding on City Hall property earlier this year, may be up to more than just connubial biz.

Back in August, Fly detailed the sordid tale of fear and loathing taking place within the Milpitas Planning Commission. Mark Tiernan, a veteran in organizing local campaigns, felt he was kicked out of his commission chair position in a coup partly orchestrated by fellow commissioner Noella Tabladillo. Tiernan said loudly in a commission meeting that Tabladillo couldn’t be trusted, and she in turn called him an asshole. Tiernan then made a bold claim to Fly that he thought Mayor Jose Esteves was behind the whole thing. Esteves is now having Tiernan removed from the commission, but there could be an even bigger things happening behind the scenes.

Move over Google, it seems public service is one of the valley’s most desired jobs. Two Cupertino councilmembers, Kris Wang and Barry Chang, are supposedly interested in the race for a seat on the county Board of Supervisors.

David Ginsborg, right-hand man to county tax assessor Larry Stone, is running for a seat on the Santa Clara Valley Water District board come next November. We’re not sure why anyone would want to spend waking hours noodling on water policy, but then again it can’t be any less exciting than tax assessments. Ginsborg isn’t the only one running against incumbent Joe Judge, though.

A political comic strip/hit-piece lampooning Cupertino Mayor Gilbert Wong was sent to 7,200 Cupertino voters over the weekend, just two days before the city’s election on Tuesday. Titled “The Adventures of Gilbert Wrong, Mayor of Cupertino,” the comic strip sets out four different scenarios in which Wong is contacted by a secretary with someone waiting to bend the mayor’s ear. Nonetheless, Wong was able to be re-elected as mayor.

Four San Jose councilmembers want City Manager Debra Figone to explain how she hires and ensures diveristy in senior staff positions. Few outside searches take place for qualified candidates, and just as few minorities currently hold director-level positions. As a result, Councilmembers Kansen Chu, Ash Kalra, Nancy Pyle, Xavier Campos and Don Rocha sent a memo to the city’s Open Rules and Government Committee asking for data. They also want a discussion on hiring practices to take place at the council level.

The state redistricting committee threw a wrench in the careers of politicians throughout California this summer by redrawing the lines. As a result, one unexpected race will pit two local, union-friendly Democrats—Jim Beall and Joe Coto—against each other in the newly established 15th State Senate District.

The most lucratively compensated of City Hall official is Debra Figone, San Jose’s city manager, who earned $239,000 last year. Figone has worked for the city on and off for nearly a quarter of a century, and since returning from a stint as Los Gatos’ city manager, she has racked up the limit of 1,200 hours of unused sick leave. All of this has set off speculation that Figone will retire sooner than later.

Oddly enough, three of the biggest stories in San Jose right now all have one thing in common: the most famous nonfiction author in America, Michael Lewis. His current bestseller, Boomerang: Travels in the New Third World, details how countries, states and municipalities are going bankrupt, and he uses San Jose as a model for implosion by pension.

Paul Fong may be chair of the state Elections and Redistricting Committee, but that didn’t do the state assemblymember any good over the summer. A citizen commission for the first time in 10 years redrew district lines, and Fong lost 75 percent of his real estate—as well as the leverage of incumbency. Fong’s district, which goes from being called the 22nd to the 28th starting next year, will no longer include Sunnyvale, Mountain View or Santa Clara, which were supplanted by the golden ghettos of Saratoga, Los Gatos, Campbell and south San Jose. All of this means Fong could face a tougher challenge than expected—and from a registered Republican no less.

After two terms in the state assembly and two in the state senate, Joe Simitian will say goodbye to Sacramento next year, courtesy of California’s term limits. The smart money is betting on a Simitian run for Congress, though Rep. Anna Eshoo will have to stand down first. Rather than take a vacation from public service, Simitian may return to the Santa Clara County Board of Supervisors.

On Sunday, President Barack Obama became the first sitting U.S. president in a decade to overnight in San Jose. That may placate some of the people who have been complaining that this president bypasses a city that overwhelmingly supported him and only spends time with the wealthy gods of social media on the Peninsula, who dispense $35,800 checks like ATMs. Truth be told, the only reason Obama was in San Jose was because he needed a place to crash.

The Bay Area’s public school system sustained another groin kick of aggressive generosity Tuesday when politically ambitious billionaire Meg Whitman bestowed $2.5 million on South Bay and Peninsula charter school programs. Apparently, the maid-firing former eBay exec didn’t spend all her money losing last year’s race for governor to Jerry Brown.

It looks like Palo Alto is about to follow in San Jose’s footsteps and is gearing up for a battle that could generate the same kind of acrimony seen last year during the Measures V and W election. The Palo Alto City Council approved a proposal this summer to put a measure on the November ballot that would repeal binding arbitration between the city and its public-safety unions.

Hewlett Packard CEO Leo Apotheker’s move to exit the consumer computer business could bring more bad news for San Jose’s budget. The Palo Alto computing colossus currently pays San Jose and the arena’s management firm $3.25 million annually to hang its sign at the HP Pavilion’s entrance. Of that amount, $1.25 million goes directly into the city’s general fund. But with the agreement set to expire at the end of 2015, and HP’s plan to spin off its line of PCs—like the “Pavilion” models—the Shark Tank’s proper name seems unlikely to stick.