Composite photo of two men's headshots
The political relationship between former New York Mayor Michael Bloomberg and former San Jose Mayor Sam Liccardo stretches back a decade, before Bloomberg backed Liccardo's run for Congress with half a million dollars.

When New York billionaire Michael Bloomberg mounted a short-lived run for president in 2020, then-San Jose Mayor Sam Liccardo became his campaign co-chair and first major California endorsement.

The relationship between the two former mayors has spanned nearly a decade — from Liccardo’s early city hall days to Bloomberg now funding his path to Congress.

“That’s where you get back to Liccardo’s ethics,” Larry Gerston, a political analyst and retired San Jose State professor, told San José Spotlight. “That’s where you get to the shady accusations that he’s vulnerable to, the emails, all of that stuff, and that’s where Bloomberg’s past comes in. Are these birds of a feather?”

Gerston said while the support might not be unusual, any moral issues about Liccardo’s history with Bloomberg would have to come from Liccardo’s opponent — Assemblymember Evan Low. Gerston said Low’s campaign could highlight the alliance and the amount that Bloomberg donated. Liccardo’s campaign could argue he’s deflecting from policy issues.

Liccardo, a former criminal prosecutor raised in Saratoga, got his start in politics in 2006 by winning the San Jose City Council’s downtown seat. He won a race for mayor eight years later and served two terms. Bloomberg and his philanthropic efforts loomed in the background, funding the new mayor’s travel and showering the city with multimillion-dollar grants during his administration.

Nine months after he took the mayor’s seat, Liccardo put in a request to go to London for a week in October 2015 — funded by Bloomberg Philanthropies. The trip, which cost nearly $4,000, was approved unanimously. Liccardo at the time defended his frequent travel, including a trip to Rome, by saying invitations from the Pope and Bloomberg don’t come around often. The trip to London was to attend CityLab‘s annual conference exploring “urban solutions” to challenges big cities face.

Bloomberg Philanthropies funded a trip to New York for Liccardo’s staffer two years later for another summit.

Under Liccardo’s tenure, the city snagged a grant from Bloomberg Philanthropies for $2.5 million to explore climate solutions and reduce carbon emissions.

Now, nearly a decade after Bloomberg’s interests flew Liccardo to London, the billionaire Democrat is funding his campaign for Congress.

Bloomberg on Feb. 7 contributed $500,000 to Neighbors for Results, a super PAC that’s been supporting Liccardo’s bid for Congressional District 16. He’s the super PAC’s largest funder next to former NetApp CEO Daniel Warmenhoven, who contributed $50,000.

Neighbors for Results has already spent almost $458,000 to support Liccardo through mail advertisements, text messages and polling. Neighbors for Results also funneled $102,000 into another super PAC named Count the Vote, which paid for a controversial recount of the congressional race. Liccardo claimed he had no part in the recount request, though it came from one of his supporters and was paid for by the fund backing him.

The recount broke an extraordinary tie between Low and Santa Clara County Supervisor Joe Simitian for second place, knocking Simitian off the ballot and positioning Liccardo in the favorable position of facing only one opponent in November.

Liccardo’s campaign denied coordinating with the super PAC, which is illegal for candidates to do.

“I’m not surprised that Bloomberg has been supportive. They have had a history of close collaboration in San Jose, working together to address climate change, gun violence and improving city services,” Liccardo campaign spokesperson Gil Rubenstein told San José Spotlight.

Rubenstein said the two former mayors met in 2018 at the Bloomberg Harvard City Leadership Initiative, a yearlong municipal leadership training program hosted at Harvard University and sponsored by Bloomberg Philanthropies. Liccardo was part of the initiative’s second cohort of mayors.

Bloomberg could not be reached for comment, and Bloomberg Philanthropies did not respond to a request for comment.

It isn’t the first time the two men shared political alliances.

Days after Liccardo’s pick for president — Kamala Harris — dropped out of the 2020 race, he flocked to support Bloomberg. Liccardo became the first big endorsement for Bloomberg and went on to co-chair his campaign in California by advising on strategy, policy and serving as a surrogate. Liccardo called Bloomberg “courageous, innovative, and pragmatic.” He even kicked off a campaign event for Bloomberg in January 2020 with wealthy donors in Pleasanton.

“I supported Kamala Harris for the same reason that I support Mike Bloomberg and that is — we’ve got the biggest bully in the history of the planet occupying the White House and I want to support those who can take down bullies,” Liccardo told San José Spotlight at the time.

San Jose Mayor Sam Liccardo speaks at a campaign kickoff event for presidential candidate Mike Bloomberg Jan. 2020 in Pleasanton. Photo by Nadia Lopez.

But Liccardo’s support for Bloomberg sparked backlash from some of his Silicon Valley political colleagues. Assemblymember Ash Kalra, who served on the San Jose City Council with Liccardo, criticized the move and likened Bloomberg to Trump.

“It is the wealthy elites like Trump and Bloomberg that have created the oppressive economic state we are in where the very few have hoarded the wealth and power over the millions struggling to get by,” said Kalra, who supported Sen. Bernie Sanders for president.

Bloomberg’s era as mayor of New York City was marred by his support for policing that targeted people of color, namely the “stop and frisk” policy which a federal judge deemed unconstitutional in 2013. Under the policy, police officers disproportionately targeted African American and Latino residents across New York City. Bloomberg, who previously was a Republican and supported Republican Meg Whitman’s bid for California Governor against Jerry Brown in 2010, later apologized for the policy. Liccardo said he believes the apology was genuine.

The three-term New York mayor dropped out of the presidential race in March 2020, after reportedly spending more than $1 billion of his own money on the four-month campaign for the White House. Liccardo then backed President Joe Biden.

Bloomberg became the target of a #MeToo controversy after facing accusations of sexual harassment, gender discrimination and allegations that his companies are hostile workplaces for women. The women reportedly signed nondisclosure agreements. Liccardo stood by Bloomberg despite the scandal which was among a string of criticism he faced on the national debate stage.

“As Democrats, we have to be keeping our eye on the prize,” Liccardo said at the time. “There is room for very healthy debate over matters of policy and record, but the individual we have to defeat is Donald Trump, or all is lost.”

Contact Ramona Giwargis at [email protected] or follow @RamonaGiwargis on X, formerly known as Twitter. Contact B. Sakura Cannestra at [email protected] or @SakuCannestra on X, formerly known as Twitter.

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