Metro Silicon Valley’s issue this week looks at possible candidates to succeed Mayor Chuck Reed when he terms out in less than two years. Invariably, in every discussion, two names pop up: San Jose Councilmember Sam Liccardo and Santa Clara County Supervisor Dave Cortese. Below is an excerpt focusing on Liccardo’s upbringing, what made him go into politics, and his interest in running for mayor in 2014.—Editor

San jose Councilmember Sam Liccardo had a big mouth as a kid, which is not uncommon for the baby in many families—or future attorneys. The youngest of five siblings, Liccardo inherited the gift of gab from his father, Sal—a personal injury attorney—and then went about putting it to good use at parochial school.

Skipping kindergarten and immediately entering school as a first grader, Liccardo was younger and smaller than his classmates until a growth spurt in high school. Speaking up was his only way to gain stature, but he says it usually resulted in him getting pummeled or spending hours in detention with other talkative prepsters at Bellarmine.

“I think Bellarmine gets a bad rap for being an elitist institution,” Liccardo says. When that argument fails to gain traction, he relents. “There’s a bit of a Bellarmine mafia in San Jose, and whatever reputation it has, it’s probably well deserved.”

Liccardo went from Bellarmine to Georgetown to Harvard—he received a law degree and a master’s in public policy—and then to the U.S Attorney’s Office in San Diego, where he became the youngest prosecutor on staff.

“It made it possible to avoid working for a law firm,” he says in a nod to his father, whose office is located in the wealthy enclave of Saratoga. When Liccardo moved back from San Diego to prosecute sexual assaults and child-abuse cases for the Santa Clara County District Attorney’s Office, he settled in rent-free into his grandfather’s North San Jose home.

In his only true election, back in 2006, Liccardo beat out labor-endorsed former State Assemblyman Manny Diaz. In 2010, Liccardo ran against a puff-pillow challenger, and his well-funded allegiances were hardly tapped as he raised about $62,000.

Once a week, Liccardo crosses Santa Clara Street from City Hall and walks to Horace Mann Elementary School, where he tutors a fourth-grader named Omar for 45 minutes. (Liccardo also teaches a political science class at San Jose State University.)

Shy, yet wearing his hair in a fauxhawk, Omar reads at a second-grade level, which why he is enrolled in the “1,000 Hearts for 1,000 Minds” program Liccardo helped create with council colleagues. A few feet from the school’s parking lot entrance, a filthy sleeping bag was left stained and sprawled on the sidewalk.

The downtown vista isn’t always pretty, but it has shaped policymakers who tune in to San Jose’s hardscrabble realities.

“Any downtown councilmember is always viewed as mayoral timber,” says Dean Munro, who served as chief of staff for McEnery in addition to working on the staffs of Reed and former mayor and U.S. congressman Norm Mineta. “McEnery, David Pandori, [Susan] Hammer, Chavez—not all were successful, but all of them were serious candidates, because of who they represented and the visibility.”

Aside from one notable indiscretion, in which Liccardo accepted tickets to a San Jose Sharks game (which is curiously impermissible, according to city rules, because public officials can accept free tickets to any event as long as it’s not sports-related), his ethical conduct has been consistent. But that hasn’t always made him popular or politically savvy.

In the last year, Liccardo took several positions that he saw as principled while others wondered whether he was a step out of touch.

When the City Council had the chance to regulate the budding medical marijuana industry in San Jose, Liccardo shirked the opportunity to lead and sided with the council majority by instituting an arbitrary cap of 10 on collectives.

Liccardo pleaded ignorance on how to handle the situation—a surprise coming from someone who left the U.S. Attorney’s office in San Diego because he felt the war on drugs was ineffective.

Last spring, when police and firefighters agreed to take a 10 percent pay cut, Liccardo surprisingly voted against the deal, because he said the concessions didn’t go far enough to solve the city’s budget woes.

Having already aligned himself with Mayor Reed’s public employee pension-reform push, Liccardo’s posturing only further enraged angry police officers and firefighters. Further criticism came when he joined Vice Mayor Madison Nguyen and Councilmembers Pete Constant, Rose Herrera and Pierluigi Oliverio in supporting Mayor Reed’s fiscal emergency declaration.

But halfway through his second term, Liccardo, 41, has toed the line adeptly during his six years in office. His missteps have been relatively undamaging, and he has picked up numerous allies while representing the downtown district interests.

He sits in a good position to slide over a few seats to the middle of the council dais, where the mayor of the nation’s 10th largest city sits. And Liccardo no longer acts coy about his interest in the job.

“A few years ago I would have said hell no,” he says, “but there’s a really good chance.”

Correction: A former version of this article incorrectly stated the amount of money Sam Liccardo raised for his 2010 council race against challenger Tim Hennessey, as well as information regarding Horace Mann Elementary School in San Jose.