Election 2020: Labor-Aligned Incumbent Faces Business-Backed Challenger in SJ’s D2

Election Day comes early this year. In fact, early voting is already a week underway in Santa Clara County, where every registered voter now gets the option of mailing in their ballots or dropping them off in person anytime from now through Super Tuesday.

Over the coming days, San Jose Inside will bring readers overviews of some of the most closely watched local races in Silicon Valley, starting with the handful of seats up grabs on the 11-member San Jose City Council. This year, the city’s even-numbered council districts are on the ballot—2, 4, 6, 8 and 10.

If a candidate receives at anything greater than 50 percent of the vote in the March 3 primary, then they win the race outright. If nobody nabs the simple majority, however, then the top two vote-getters move on to a runoff in the November election.

To kick off our election series, we’ll start with District 2, where Councilman Sergio Jimenez is defending his incumbency against Jonathan Fleming.

The District  

District 2 encompasses some of the southernmost swaths of San Jose, including Santa Teresa, Coyote Valley and Monterey Road.

It’s a diverse swath of the city that abuts Evergreen to the north and extends south just short of Morgan Hill’s Madrone neighborhood. It covers vast expanses of open space—sidling up next to Coyote Valley—and vast tracts of single-family homes.

It’s a district that’s booming with new development and grappling with issues shared by most of the city: a dearth of public transit access, rising traffic collisions, residential displacement and a burgeoning population of homeless people.

The Incumbent

Forty-three-year-old Sergio Jimenez hopes to capture a second term by touting some of the greatest hits from his first four years in office and his record as one of the most prolific policymakers from the progressive wing of the mostly business-aligned council.

Born in Mexico, Jimenez moved to California with his family at the age of 3. Raised by a single mom, Sabina, with his siblings in a small apartment in San Jose’s East Side, Jimenez graduated from Independence High School and went on to earn his citizenship in 2008. According to his campaign bio, he also became the first person in his immediate family to earn a college degree: a bachelor’s in political science from San Jose State.

Before winning elected office in 2016, Jimenez worked for eight years as a crime investigator for the Santa Clara County Public Defender’s Office, where he says he witnessed firsthand the intersection of poverty, violence and crime.

A longtime resident of D2, where he lives with his three children and wife Patricia, Jimenez says his history of public service—which includes his founding of the Oak Grove Neighborhood Association and six-and-a-half years of volunteering on San Jose’s Parks and Recreation Commission—sets him apart from his challenger.

(Graphic by Grace Hase)

“Public service has been a consistent theme of everything I’ve done,” he tells San Jose Inside. “It isn’t something that I’ve just grown into as of late—that’s a big distinction. I think, based on the stories I’ve heard, I believe that I have the right temperament to handle some of the tough issues before us.”

Jimenez says he’s running for re-election to continue the work he started. He wants to continue advocating for the conservation of Coyote Valley and to finally secure an agreement with Union Pacific Railroad to resolve some of the issues—train noise, trash. homeless encampments—along Monterey Road.

One of his biggest priorities, he says, is to apply a “laser-like” focus to homelessness.

“I think it’s the issue of our day, and we need to really dig in deeper and in a much more meaningful way to address the many residents that are living on the streets,” Jimenez says. “I’m interested in deconstructing the whole process and figuring out where the challenges are, limitations are, where we’ve had some setbacks, re-evaluating how we’re spending the money [and] furthering and deepening the relationship with the county.”

On top of that, the first-term council rep says he wants to start having “very deep and long-needed conversations” with the community on how to address homelessness in D2.

Jimenez also represents the city on regional governmental bodies, including the Caltrain Local Policymakers Group, the VTA Policy Advisory Committee, the Local Agency Formation Commission and the Association of Bay Area Governments.

Though the council is non-partisan, Jimenez is a registered Democrat, enjoys the backing of organized labor and favors progressive policies such as charging developers fees to pay for affordable housing, tenant protections such as eviction and rent controls and sustainability measures that limit the city’s carbon footprint.

During his first term, the D2 councilor has also prioritized the kinds of quotidian services in high demand from residents, such as litter abatement and public safety. In the 2018-19 fiscal year, he helped secure $1.5 million in the budget to open the long-idling San Jose Police Department South Substation—an achievement he considers a major victory, considering how the facility languished empty for years because of a lack of funding.

The Challenger

A veteran of the engineering industry—where he spent years working in the defense sector and designing technologies such as a blast-mitigating vehicle seat that protects soldiers from fatal brain injuries—36-year-old Jonathan Fleming is a new face in D2.

Born in Los Angeles, Fleming moved with his family to the Bay Area in 1992. Per his campaign bio, he went on to graduate from Santa Clara University with a degree in mechanical engineering, which led to his work in the high-tech sector.

Fleming’s path to civic service began during his healing from a catastrophic car crash, which he says forever altered the course of his life. Ten years ago, with traffic at a dead stop on I-880, Fleming says he was rear-ended by an 18-year-old motorist traveling at 85 mph without hitting the brakes.

That collision plunged Fleming from full health to permanent disability. It took 23 surgeries and years of therapy to mend his broken limbs. During one of his walks for physical therapy, Fleming says he encountered a neighbor who told him about a project that he felt would threaten the safety of the neighborhood. After some research, Fleming gathered signatures to oppose the project, which set him on a path of civic activism.

A dyed-in-the-wool, tax-and-regulations-averse, libertarian-leaning conservative with backing from the city’s business leaders, Fleming moved to District 2 about a year after losing a 2018 bid for then-Councilman Tam Nguyen’s seat in District 7.

Months after last year’s general election, Fleming and his wife Kristel decided to move out of the East San Jose district because they no longer felt safe raising their 2-year old daughter in their Senter Road neighborhood.

Fleming says he initially didn’t plan to run in the new district he called home, but changed his mind after residents began asking him to challenge Jimenez in 2020.

(Graphic by Grace Hase)

“His failed policies of tax, tax, tax—they’re just not ringing true, and people aren’t seeing the results,” Fleming says of Jimenez. “They look at me as someone who listens to the community, somebody who participates with the community and someone that designs solutions that will help us all out.”

As California’s intractable housing crisis drags on and younger residents flee for cheaper locales to raise their families, Fleming says getting new housing built is one of his top priorities. To achieve the level of construction San Jose needs to dig its way out of this mess, he says he wants to remove bureaucratic “red tape” by lowering fees and easing regulations for developers. Fleming says he also wants to streamline the city’s permitting process and “stand firm against implementing stricter rental policies in an effort to increase the supply of housing units.”

If elected, Fleming promises to draw on his experience as a neighborhood commissioner, a role he held from 2016 to 2018 as chair of an ad-hoc working group on homelessness. During those two years in that volunteer position, he says he advocated for more public outreach about future developments, such as San Jose’s proposal to build small sleeping cabins—called “tiny homes”—for the homeless.

As founder of the Senter Monterey-San Jose Neighborhood Association, Fleming says he wants to continue the kind of community engagement he fostered through that group and to ensure that residents’ voices are heard.

The Stakes

While the stakes are high in most of the five city council races as labor-interests seek to either hold onto or flip a seat, local political observers tell San Jose Inside that’s not necessarily the case in District 2.

“I think it's more about utilizing [Jimenez's] voice as a catalyst for what can happen in this upcoming election,” according to one campaign consultant.

Politicos interviewed for this article predict a clear win for Jimenez, who landed a coveted Mercury News endorsement—no small feat for a labor-aligned contender.

“For the most part [D2 is] a fairly happy community,” the same consultant says, “[and] the only person who stepped up to challenge him is not exactly a very strong candidate.”

Previous Coverage

San Jose Council Hopeful Stumbles Upon Rival's Event While Door-Knocking in D2

BAYMEC Unveils Endorsements for March Primary Election


  1. There is no greater threat to solving Homelessness than Councilmember Jimenez. His resentment and hate of property owners made it impossible for him to see the very real consequences of rent control. That regime of laws has lead to a massive increase in evictions, 20000+ since 2017. When warned of the reality of rent control, he just laughed and quiped, “cry me a river”. Now homelessness is up 42% since he and his compatriots got the revenge they sought on landlords.

    Not only id Councilmember Jimenez culpable is a massive spike in ruin lives, he has blocked new develooment and added to the red tape rewuired to build housing inventory. Always the wotd smith his dumbing down of the debate over UGBs through the slogan, “Measure B for Billionaires, measure C for Community” lead to the poison pilling of vast swaths of land indefinitely. CEQA and UBG are very real problems to the lives of renters and those who wish engage in the American dream.

    Either Concilmember is ignorant to the fact that his agenda hurts working class and aspirational residents of D2 or he is acting in the interests of real estate investors to permanently evict poor people and stiffle development, who knows. But I do know he is wrong in a way that cant be fixed, and needs to go before he destroys more lives.

  2. Where do I begin with Jimenez? He is in a voting bloc of 5, claims to be a “proud Democratic Socialist, never met a tax he didn’t like, has rarely ever communicated with D2 residents, has said the crime statistics in D2 is hysteria (his word) because of Nextdoor, consistently, continually votes along labor union interests, is for redistributing funds given through the budget process from D2 to other neighborhoods, falsely accuses Fleming of having moved from one district into D2 to run against him (Fleming moved because a gun battle was going on and he lay on the floor huddling his scared daughter), fought hard for Measure B and enlisted college students to help that Measure pass, and on and on and on. If anyone opposes his ideas, he says or implies they are racist, on and on and on. Even the Mercury said they PAUSED before supporting labor-backed Jimenez and said of Fleming that he was the most fiscally conservative of the two. Jimenez looks out for the interests of labor unions, never D2 interests. He will tell you he voted against Measure E as if he is against higher taxes. Actually, he said he was for A tax (linkage fees….against businesses) but not THAT tax (Measure E). This is just the tip of the iceberg of what Jimenez has done or not done to help destroy D2. If you want higher taxes, Jimenez is your guy; if you don’t want higher taxes or the funds given to D2 through the city’s budget process to be redistributed to other Districts, Fleming is your guy.

  3. District 2 is a very divided district due to our current councilman’s posture. He asks for unity that means that all of us should think like him and who does not will be suppressed by his supporters until the “unity” silences who thinks differently. Mr. Fleming asks for us to be united and being united does mean we should all think the same and it is okay to think differently. We can all be united and work together for common goals. He came from a very diverse district and is used to diversity.
    Mr. Jimenez shows that he likes to create “divisiveness” since he is part of a group that is breaking our city council apart and he is known for not being easy-going. The use of the word Unity by Jimenez shows clearly that is all about silencing who does not think like him. He earns votes helping special interest groups and not by uniting our community.
    Jimenez also doesn’t seem to be able to unite our community or remain neutral when he is learning about something. Neighbors gave up going to his office hours. His office hours has very low attendance due to his lack of sensitivity to try to understand who does not feel like him or his lack of empathy for those who are concerned about something that he is not seem to care. Some examples of his lack of leadership or people skills were the issues with the tiny homes process and the development at Blossom Hill and Snell. The meeting about the tiny homes had more than 700 people who were concerned, and he did not seem to be able to manage the process that was obscure since the beginning.
    The second meeting organized by neighbors had at least 500 people and our neighbors were called “gang” by his supporters who contacted “the fly.” If he was a good leader he would have known how to communicate properly with his constituents. These two situations would have been managed in a less stressful way for all the parties involved. During the last debate SJ lied about the development at Blossom Hill saying that was going to be only for seniors since the beginning when the developer contacted him. He was telling to all the neighbors that is low income as formerly homeless were not part of it. He puts neighbor against neighbors. One side are those believe him and the other side who saw discrepancies in his statements. The developer worked with neighbors and decided to follow their advice to house seniors and have never omitted that formerly homeless were moving in as Sergio did.
    Sergio infuriated neighbors during the meeting about the tiny homes, he wanted to have a class about homelessness instead of explaining to the neighbors present what the project was about.
    I see a lot of difficulties in the next four years if Sergio is re-elected due to this lack of empathy for his constituents feelings, arrogance, lies, leadership skills and inclusiveness of those who are not part of the “unity” team.
    We need someone who is not so involved with special interest groups like unions and need more someone who is more a community leader who knows how to keep this district United and shows empathy. This person does not need to do what we ask all the time. But it is important to be able to not be biased during the decision process.
    Sergio shows lack of empathy for neighbors who were victims of a crime, or saw crime next to their homes. He says that is all social media histeria. He completely denies the that some homeless can commit crime or some have addiction problems and even our police chief mentioned that are safety concerns about encampments near neighborhoods. Sergio told his constituents to do not have fear. Jimenez was very proud to state during the debate that he was investigating the police in his previous job but he can’t admit that homeless need help with addiction or mental illness and can commit crimes too.
    Mr. Fleming is a better choice than Mr. Jimenez because he seems to be able to show empathy for his neighbors and homeless. He is not in denial that homeless need help with having access to treatment, he witness crime at his previous address and understands the traumatic side of it, he founded the district leadership group in district, had a neighborhood association, and his life history that includes almost losing his home, and helping friends who because homeless and had issues with addiction. Mr. Jimenez did very well so far with his life and does not seem that he experienced so many difficulties due to his lack of empathy.
    I hope Mercury news made another mistake about the election results because if Sergio is re-elected it will be a very difficult healing process because all the divisiveness he caused in our district and at the council. This is not about qualifications but about personality. If he wins he needs to learn people skills and to be more inclusive. Or he will have very little support or will only have support from those who are union or neighborhood association. The damages he caused due to his lack of empathy, and using divisiveness are greater than it seems. He is a champion for having a college degree, working as a councilman, being an immigrant who succeeded, but he lacks empathy for those who have a different story than his or are not part of his agenda.
    His divisiveness tactics need to come to an end. And a way to unite our district is a new leadership that is more inclusive, and respects different opinions.

  4. Thank you for the great article Grace. There is some additional information I would like to add to the comments section:

    My family first called San José home in the late 1800’s. My great-great-grandmother was a painter and raised my relatives here. I graduated Santa Clara University with a degree in Mechanical Engineering and have called San José my home since. I was recognized by US Senator Udall for, “Saving American Lives in Combat” for my engineering design as a civilian contractor.

    I have overcome disability because I never quit and I will never quit fighting for you when I am elected to represent our District on the City Council.

    The three areas I want to expand upon are:
    1. Improve Safety – Hire More Police Officers
    2. Address Homeless Compassionately with the Fleming Homeless Plan
    3. Fiscal responsibility without Raising Taxes

    1. Improve Safety – Hire More Police Officers

    The highest priority of the San José government is to protect life and provide for the safety of its residents. Since the last election in 2016, our quality of life has worsened as demonstrated by the 20% increase in crime.

    Low police staffing is the primary reason for our City’s increasing crime rate because we are stuck in a permanent reaction mode. As Councilmember I will work to increase our Police staffing ratios to national levels while maintaining high applicant standards.

    – Short term goal of increasing staffing to 1,450 Officers
    – Will advocate for a competitive and fair wage/benefits package, including medical, to attract and retain Officers
    – Restore confidence and trust between the this council office and our Police
    – Hire more dispatch personnel to reduce 911 and 311 response times
    – Predictive policing software and modeling need to be used effectively to ensure officer safety and reduce crime levels.

    As Councilmember I will advocate for specialty Police units, specifically the Gang, Traffic, and Graffiti units as I believe that focusing on these areas will improve the efficiency of patrol officers and sharply reduce crime throughout our City. It is a fact that patrol officers responding to a murder, traffic accident, or some other crime consume more resources and create call backlogs as opposed to preventing the crime in the first place.

    2. Address Homeless Compassionately with The Fleming Homeless Plan – https://www.votefleming.com/homelessplan

    I have firsthand knowledge of homelessness because I almost lost everything after my own disability and I have lived with four homeless persons, who I invited to live with me for free under my own roof.

    Prevailing strategies and policies are protracted and limited while enable homelessness by precluding treatment of its underlying causes: mental illness and substance abuse.

    The Fleming Homeless Plan focuses on rehabilitation emphasizing sobriety, treatment for mental illness, and job placement through immediate housing in prefabricated university-like campuses away from schools and neighborhoods, with a goal of self-supportiveness while saving half a billion dollars in construction costs over current practices.

    The Fleming Homeless Plan is built upon compassion, fulfilling a vow to fix the system after I was victimized during my own disability. It is the product of four years of research on homelessness, partnering with the academic community at San José State University.

    3. Fiscal responsibility without Raising Taxes

    Our City needs to use your tax dollars correctly and grow our City’s general fund without increasing tax rates or levying new bonds to improve our core services and give us a better quality of life

    The residents of District 2 and San José are overtaxed and are not receiving the services they were promised. Our City budget continues to increase and we are not seeing the results.

    The City Auditor reported that the overwhelming majority of our residents, 81% to be exact, stated the city returned a poor or fair return on our taxes which were the two lowest grades possible.

    It is time for new representation. As Councilmember, I will not vote for another tax increase. We need to see results from the high taxes we already pay.

    Please visit my website at VoteFleming.com to learn more about our campaign and our new ideas to make San José safer, cleaner and better for us all!

  5. Let’s read what taxpayer watchdogs have had to say about Fleming and why they are endorsing him:

    I am honored to receive the endorsements of the Silicon Valley Taxpayers Association and the Citizens for Fiscal Responsibility!

    San José is too expensive for most of us and more taxes are not the answer. We need to stop wasting money on programs that do not work, reevaluate current policies, and develop new solutions to improve our everyday quality of life in San José.

    We are worse today than three years ago. Homelessness has risen 52%, crime has risen 20%, and our taxes are higher than ever. We need a change!

    It is time for a new representative in south San José and I look forward to working with you all! Vote Fleming on March 3, 2020!

    About our endorsements:
    “The Silicon Valley Taxpayers Association is dedicated to protecting the rights and interests of the taxpayers of Silicon Valley against the over–reaching and over–spending of government.”

    “Citizens for Fiscal Responsibility is dedicated to advocating a responsible approach to government that will achieve fiscal, economic, and environmental accountability and sustainability, as well as a desirable quality of life for current and future generations.”

  6. I won’t argue the fact that Jimenez has seemingly made the most of his upbringing and has attained a level of success – kudos to him for that. I will say that as a council member, he is not nearly as successful. My family has lived here for decades and I have never seen such anger, frustration and disappointment in District 2 as we are currently seeing.
    It has been clear to many of us that Jimenez does not serve his constituents – he has an personal agenda he follows and he often aligns himself with a group on the Council rather than representing what his constituents actually want or need.
    He gives lip service to being open to discussion but his office hours and other engagements with the public have proven that not to be true. After attending events with him I have given up trying to make myself heard because he clearly will not listen or give any respect to anyone with views different from his. He has the attitude that only he knows best and gives little consideration to the views of the people who elected him to office. I am embarrassed to say that I believed what he said in his first campaign but his actions have proven who he really is. He gives himself credit for various Council decisions in which he was perhaps a part of, but in no means was an initiator or leader. His talent for getting by on the coat tails of others is evident.

    Out of desperation I began researching Mr. Fleming several years ago, wishing we had someone of his caliber in D2 who would run against Sergio. When D2 residents reached out to him for consultation, he enthusiastically and generously responded. Fleming has impressed many of us with his intellect, his thoughtfulness, his interest in and respect for all he speaks with, and his desire for fiscal responsibility. He wants to work in partnership with his fellow neighbors which has been so lacking under Jimenez. Once you interact with Fleming one on one, you know immediately you are dealing with a man of confidence and character. This is a guy who, after a heated debate, offers his hand to his competitor – only to be rebuffed by Jimenez. Who in the public sector, whose job is to interact and engage with others on his constituents’ behalf in a positive way, behaves like that? Such a lack of respect deserves a lack of respect in return.
    Jimenez has implied he has felt under attack at neighborhood meetings – isn’t disagreement a part of the equation when you are an elected representative? This man must have been wounded in the past and seems to expect special consideration as a result. This is a man who lacks the self esteem to be a leader and operates under some degree of paranoia. He may be an adequate representative for SOME, but District 2 needs and wants a representative for ALL.

    I have never been active in a political campaign for office before, but circumstances we are facing are driving me to work for the best person for this job. It is imperative we vote for a change in District 2.

    We need a man of ethics who will bring new and exciting ideas to the Council, such as The Fleming Plan for Homelessness. We need a man who sees a problem and will work tirelessly until it’s successful resolution. A man who was once told he would never walk again is the man of fortitude and confidence we desperately need in District 2. Our district has been in decline for several years and it is going to take a lot of hard work from all of us to improve the situation we are in. That is why we need the leadership talent and desire for inclusiveness that Jonathan Fleming will bring to District 2. #VoteFleming.

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