In what may turn out to be one of the most expensive races ever for a local county office, Cindy Chavez has captured the District 2 Supervisor seat held by her disgraced former ally, George Shirakawa, Jr. The victory places the largest county government in the global home of leading edge technology—from Teslas to Google Glass—firmly in the hands of an old-fashioned political machine; a classic one that delivers votes, wins elections, rewards its followers and dispenses benefits. Over the next two years, the board will vote on billions of dollars in employee compensation contracts—the county spends $3 billion a year on salaries, benefits and pensions—for the members of the unions who returned the former San Jose city official to public office.

Well over $1 million was spent in the political sprint, the majority by Chavez’s campaign and a network of public employee union-aligned committees. According to a review of the latest campaign disclosure filings with the county and Secretary of State’s office, the Chavez campaign and the committees it coordinated with spent no less than $752,000 on the primary and runoff, and that total should be much, much higher when all forms are counted. This total does not include any money spent on mailers by the South Bay Labor Council’s Committee on Political Education (COPE), which has aggressively campaigned on Chavez’s behalf.

Chavez benefited from a compressed election cycle orchestrated by her allies on the Board of Supervisors over the objections of community members who appealed for an Aug. 20 election. Activist Omar Torres argued for the three extra weeks, saying, “Our community is fed up. ... We want a candidate who will be beholden to the community residents of District 2, not to the powerful interests who have long dominated Santa Clara County politics.”

The brief, low-turnout balloting during the dog days of summer benefited the candidate with an organization at the ready and interested parties to tap for contributions. It’s a machine that has its roots in the 1990s, when Chavez’s mentor, Amy Dean, rose to the helm of the South Bay Labor Council. To boost the labor council—a measly six-figure operation—Dean incorporated a tax-exempt non-profit to squeeze money out of the foundation community. The 501c3 Working Partnerships USA would bring in more than $25 million in donations over the next 15 years, according to tax filings.

“Our first big win with a local candidate was the election of Cindy Chavez to the City Council in 1998,” Dean wrote in a 2003 essay titled, “Taking Over City Council.”

“In 2001, we continued to organize for working class power on the City Council by throwing our energy behind Nora Campos, a young Latina from the East Side (the low-income district of San Jose), who won a three-candidate race outright with over 50 percent of the vote.” Campos is now Speaker pro Tempore of the California State Assembly and her brother, Xavier, sits on the San Jose City Council.

Dean called the following year’s campaign to elect Terry Gregory “our most important race.”

“In November 2002, a decade of political work and strategizing by the South Bay Labor Council of California culminated in the election of candidate Terry Gregory to the San Jose City Council. Gregory became the sixth member of the 11-seat council elected on the basis of their support for the Labor Council’s progressive working class agenda. For the first time the nation’s eleventh largest city would be governed by a council committed to working class issues.”

Adept at counting votes and marshaling majorities, Chavez served as Mayor Ron Gonzalez’s de facto whip on the council, leading to her appointment as vice mayor.

But labor’s moments of glory would be short lived. Two years after Gregory joined the council, he was censured for taking gifts and not reporting loans while in office and resigned a few months later as part of a plea deal. Chavez meanwhile became embroiled in the Norcal trash scandal when she voted to retroactively approve $11 million in additional wages paid to trash sorters in a union deal negotiated secretly by Mayor Gonzales four years earlier. Chavez was called before the grand jury three times and answered “I don’t know,” “I don’t recall” or “I don’t remember” more than 75 times in response to questions about what she knew about the trash pact.

Chavez’s credibility was further damaged two years later when she introduced a plan to give $4 million to the San Jose Grand Prix a day before a council vote, even though she had met with race officials to discuss the subsidy five months earlier.

The scandals cost Chavez her opportunity to become mayor in 2006. She was soundly defeated by Chuck Reed, who stayed on message with a campaign that promised honesty, accountability and fiscal responsibility.

Chavez then started a political consulting firm that was hired in 2007 by the East Side Union High School District, then chaired by Shirakawa, to organize a charitable foundation. She was paid $79,000 but didn’t file the incorporation papers or seat a full board. The foundation raised few donations and later lost its nonprofit status.

In 2009, Chavez returned to the South Bay Labor Council, where she had been political director prior to being elected to San Jose City Council in 1998. She succeeded Phaedra Ellis-Lamkins as CEO of the labor group and its sister organization, Working Partnerships.

For two years, Chavez also served as co-chair of Team San Jose, the hotel tax-funded labor-business coalition that operates San Jose’s public theaters, convention center and visitor marketing bureau. Losses shot up to $8.5 million during one year during that period, forcing the city to call a default and oust management and board leadership.

Labor suffered other setbacks in San Jose, as pension reformers won council seats and allies defected, costing it the council majority. A series of pension reform ballot measures further eroded labor’s power.

At the county level, however, the labor coalition maintained its majority, with Dave Cortese, Ken Yeager and Shirakawa championing initiatives crafted by Working Partnerships strategists.

The county supervisors approved a series of contracts that poured money into Working Partnerships. WPUSA was paid to lobby for municipal ordinances to ban smoking in outdoor dining areas; to serve healthy meals and juice drinks at union halls; to register voters; to advise the county on health care policy. Hundreds of thousands of dollars flowed into WPUSA to pay for programs, as well as staff and executive salaries.

The county also funded SBLC-controlled non-profits such as the Santa Clara Family Health Foundation, which steered monies to Working Partnerships and Labor Council campaigns and consultants during two attempts, one successful, to raise county sales taxes by half a billion dollars.

Supervisor Shirakawa’s arrest for using public funds and campaign money to support his freewheeling lifestyle put labor’s power at risk and drew attention to the county contracts. Labor had lost San Jose’s 18th floor and could not afford to lose Hedding Street.

SBLC took the biggest risk a chess player can take: It threw the queen into play. The most powerful actor can knock out other players more effectively than other board piece, but if the queen is captured in a miscalculation, the game’s over.

Chavez declared for District 2 and hit quickly with a swarm of social media buys, lawn signs and precinct armies. She got four pieces into district mailboxes before Alvarado had her first one stamped.

“Labor needs this race. They need it desperately,” said Dr. Larry Gerston, a San Jose State University political scientist and TV election commentator, in the days preceding the District 2 balloting. “The days in which labor was dominant in Silicon Valley are far behind us.”

Gerston believes that labor will try to use Chavez’s victory to “help re-energize and use it as a springboard for 2014,” meaning the contest to succeed Reed as mayor of San Jose.

If the 2013 supervisor race proved anything, it’s that Chavez and her allies understand how to get everyone on the same page. The campaign, working in coordination with the Santa Clara County Democratic Central Committee and the South Bay Labor Council’s Committee on Political Education, targeted Democratic District 2 voters with studied precision. SBLC pinpointed union members and their families with targeted mailers that rarely went negative—except to suggest that her opponent was a closet Republican being backed by unnamed shadowy, headless tie-wearing special interests. (Chavez ensured her opponent would have to form uncomfortable alliances by absorbing Alvarado’s natural base.) Meanwhile, the DCC’s vast email and home address database, honed during its recent county-funded voter outreach and registration initiatives, allowed it to target anyone who registered as a Democrat, regardless of whether they were formally affiliated. The trio then hit the phones and doorbells with a consistent workforce that easily outflanked Alvarado, whose campaign may have had outside committees spending on her behalf but lacked Camp Chavez’s cohesion. Firefighters, nurses and county attorneys unions formed their own independent expenditure committee to support Chavez, flooding websites with banner and sidebar ads that featured a consistent message in English and Spanish.

The machine’s ability to stay on message and drown out opponents worked as flawlessly as it ever has, leveraging allegiances from California Democratic Party Chair John Burton to Lt. Gov. Gavin Newsom making weekend visits for fundraisers.

Even Sheriff Laurie Smith, a Republican, got into the act, spending the campaign’s final day going door-to-door on Chavez’s behalf. Smith could face a serious challenge in her re-election bid next year, as peace officer unions have started to rally behind her challenger. But while Smith’s efforts in the supervisor race may not keep the SBLC base on her side, having Chavez to support her budgets when they come before the board can’t hurt.

With Chavez’s victory now secure, the machine has deftly shifted from dominating the nation’s 10th largest city to now controlling America’s 16th most populous county. Chavez and her labor-aligned supervisors, Cortese and Yeager, will find few disagreements, while Supervisor Joe Simitian is not so foolish as to rock the boat, with a future congressional run in mind and money to be raised.

With two decades of bare knuckles political experience and the ability to overcome scandals and setbacks, it will be only a brief moment before Chavez grabs the steering wheel from her less cutthroat colleagues.

Josh Koehn contributed to this piece.

More information on Working Partnerships, South Bay Labor Council and Cindy Chavez can be found at SanJoseInside.com (enter a term into the search box for full archives).