Liccardo received a bachelor's degree in government from Georgetown University, where he graduated magna cum laude and Phi Beta Kappa.

[11] The statewide homebuilding industry vocally opposed the measure, and sued after its passage; subsequent litigation prevented its implementation until the California Supreme Court eventually sided with the City of San Jose in 2015.

In the decade prior to his election as mayor, San Jose saw retiree pension and health care contributions nearly quadruple as a result of retroactive benefit increases, poor market returns, and rapidly rising unfunded liabilities.

[33][34][35] As Mayor, Liccardo has pushed for transit, cycling, and other alternatives to the automobile in San Jose, a city that grew rapidly in an auto-dominated, suburban model in the 1950s and 60s.

Both during his time as City Councilmember and mayor, Liccardo served as a board member of the Valley Transportation Authority (VTA) (which he chaired twice) and Metropolitan Transportation Commission (MTC), advocating for the creation of a bikeshare program, expansion of Bay Area Rapid Transit (BART) to San Jose, and for the launch of the region's first bus-rapid-transit line, all of which began operations during his mayoral tenure.

[47] Liccardo has also urged more innovative approaches to supplant the region's plodding, poorly performing light rail, such as autonomous, electric bus rapid-transit.

[64][65] Mastercard's CityKey technology enabled unhoused to safely keep cash, while preventing purchases in such businesses as liquor stores, and could be used to facilitate the provision of health and other services.

The "Open Homes" program help victims of natural disaster find emergency housing with an AirBnB host without cost,[66][67] and since its launch in San José, now serves cities globally.

[80][81][82] Liccardo vowed to push to find a successful alternative, and in 2019, he partnered with SiliconValley@Home and other affordable housing organizations to put Measure E—a supplemental transfer tax on properties sold for $2 million or more—on the March 2020 ballot.

On February 21–22, 2017, after one month of heavy rainfall, Anderson Dam overspilled, causing the Coyote Creek flooded in central San Jose, displacing 14,000 people.

In 2015, Liccardo publicly expressed a desire to halt plans for large-scale development in Coyote Valley—an environmentally sensitive, little-developed area south of San Jose—instead preserving it as wildlife habitat and open space for future generations.

[103][104] After overwhelming support of Measure T from the electorate[103] the City worked with POST and OSA to consummate a transaction for almost 1,000 acres of land, and the Council unanimously approved it.

[113] Mayor Liccardo advocated for the adoption of a Community Choice Energy program as a way to take action against climate change while President Trump's administration turned back to fossil fuels.

[133] After Amazon generated extensive national news coverage for its "beauty contest" of cites for its "HQ2" campus, Liccardo wrote an op-ed in the Wall Street Journal asserting that San Jose would not offer any public subsidies or tax breaks—and urging other cities to follow suit.

[135][136] For several years before the 2017 announcement, Liccardo had repeatedly sought to encourage Google to consider a Downtown campus, and in late 2016, met with executives to discuss plans for an expansive project that would comprise twice the size of Apple's nearby global headquarters.

Liccardo apologized for failing to sooner include his wife's property in his annual public financial disclosures, but the City Attorney concluded that there was no legal conflict of interest because the condo was not sufficiently proximate to the project.

[144][145][135][146] Google made a separate public commitment of a $1 billion revolving fund to finance affordable housing in the San Jose metro area.

In response, Liccardo partnered with several organizations, including Destination:Home, Cisco Systems, and the County of Santa Clara to launch the Silicon Valley Strong Fund to support struggling families and small businesses.

Within a month, the group raised more than $20 million of private donations[148] which the City matched with federal Cares Act dollars as well to provide local direct relief for struggling families.

Liccardo faced no major challengers in his reelection bid, with the Mercury News reporting ahead of the June 2018 primary election that he was "virtually guaranteed to win.

[154] In 2019, Liccardo announced[155] a first-in-the-nation initiative to require that gun owners pay annual fees to fund violence-reduction efforts, and to retain liability insurance.

In the meantime, the initiative spurred several state legislators–such as in California[162] and New Jersey[155] – to introduce similar requirements of their own, often referencing San Jose’s spearheading efforts.

In 2022, Liccardo and the City of San Jose were sued for alleged failure to disclose official communications in violation of the California Public Records Act.

[163] The lawsuit was brought by non-profit news outlet San José Spotlight and the First Amendment Coalition after Liccardo denied the existence of and refused to find official communications on his personal email account in previous public records requests.

[169] Two voters in the district submitted recount requests: Jonathan Padilla, a past Liccardo campaign employee,[170] and Dan Stegink, a former San Mateo County Supervisor candidate.

"[175] At the conclusion of the recount, in which several ballots not previously counted were deemed admissible, Simitian was ultimately eliminated and Low advanced to the general election by a 5-vote margin.