Voters have big choices to make this election about the future of San Diego County government, including a sales tax hike and a sweeping rewrite of the county’s charter.
But with so much on the ballot, one supervisor race that attracted plenty of attention and money in years past has become more low-key.
The race to represent central San Diego and parts of East County on the Board of Supervisors is pitting incumbent Democrat Monica Montgomery Steppe against former La Mesa City Council member Kristine Alessio, a Republican.
Many of the key issues defining county government have divided the two candidates, including its finances and how to respond to big changes made by Congress and the Trump administration to social services programs.
Montgomery Steppe is looking to be elected to her first full term as supervisor. In 2023, she won a special election to serve out the remaining term of former Supervisor Nathan Fletcher, who resigned amid sexual misconduct allegations.
Running on records
With nearly three years as a supervisor behind her, Montgomery Steppe said in an interview her biggest accomplishments have been in criminal justice and social services.
At the county, Montgomery Steppe has successfully pushed to phase out the use of pepper spray on juveniles incarcerated at county facilities, a practice already banned in most U.S. juvenile detention systems.
At her urging, the county is also in the early stages of launching a temporary program to provide food and healthcare for CalFresh and Medi-Cal recipients who face stricter eligibility rules under federal changes to those programs.
“I’m in the trenches doing the work,” Montgomery Steppe said. “My hope is that the voters will honor that.”
In an interview, Alessio touted her own record as an elected official in La Mesa.
A member of the City Council from 2012 to 2020, Alessio names among her top accomplishments a smoking ban on city sidewalks.
She also galvanized support for a 2014 ballot measure to impose term limits on city leaders. Term limits are a timely issue in county politics with the coming ballot measure — backed by Montgomery Steppe — to rewrite the county’s charter, including extending term limits for supervisors from two, four-year terms to three. That means sitting supervisors would be able to run for an extra term.
“I think politics lends itself to people with egos and people who are attracted to power,” Alessio said. “You need to have fresh faces, fresh ideas.”
Before running for supervisor, Alessio has twice run for office in La Mesa unsuccessfully.
In 2022, she lost a bid for mayor, garnering 44% of the vote.
Another loss came in 2024 when she tried to win back a seat on the City Council, whose members are elected at-large. She came in third in that race, trailing Genevieve Suzuki by about 750 votes.
Now, nearly six years removed from holding elected office, Alessio says being a victim of the January 2024 floods compelled her to take another swing at politics.
Alessio owns Quarry Self Storage, a storage facility in Spring Valley.
The county has an open space easement on the facility’s property, which includes part of a creek. But during the floods, the creek overflowed, flooding the storage facility with 3 feet of water and destroying the property of its tenants, according to a lawsuit Alessio’s business filed against the county later that year.
The lawsuit alleges the county violated its easement agreement by allowing trash and other debris to build up in the creek, triggering it to flood.
The flood caused $372,000 in damage to the storage facility, the lawsuit says. Alessio was on the hook for all those costs.
“We didn’t have flood insurance because we are not in a floodplain,” Alessio said. “This has been for myself, for thousands of other people, a tortuous experience.”
Similar to the legal tactics of the city of San Diego as it faces lawsuits from flood victims, the county has counter-sued Alessio’s business, according to legal filings.
County spokesperson Donna Durckel declined comment on the pending litigation. The county has hired a San Francisco law firm to litigate the case, and Durckel did not return a request for comment on how much the county has spent on the outside firm.
“No one should have flooded, and no one should have had to sue them,” Alessio said. “When I saw that my opponent was running unopposed, I said, ‘You know what? This is for the flood victims.’”
Montgomery Steppe declined comment on Alessio’s lawsuit against the county, but expressed sympathy for what her opponent has experienced.
“When any person goes through something like that, it is catastrophic,” Montgomery Steppe said. “It’s extremely emotional and I want to honor that.”
Read more Judge temporarily blocks border wall construction in Texas’ Big Bend region
Sales tax disagreement
On county finances, Alessio and Montgomery Steppe have their biggest divergence.
Alessio is an opponent of a countywide ballot measure — backed by a coalition of labor unions and nonprofit leaders — for a half-cent sales tax surcharge.
The tax hike is estimated to bring in up to $450 million to county coffers in its first year, with monies earmarked to fund social services, firefighters and efforts to mitigate the sewage crisis in the Tijuana River Valley.
Montgomery Steppe backs the ballot measure, calling it a means for the county to gain independence from the federal government and shield vulnerable residents from the Trump administration.
“We’re not talking about a charity case here,” Montgomery Steppe said. “We’re talking about the well-being of an entire region.”
The heart of the ballot measure is a response to how Congress and the Trump administration has changed who is eligible for Medicaid, administered in California as Medi-Cal, and the Supplemental Nutrition Assistance Program, or SNAP, administered here as CalFresh.
New rules passed by Congress last year require many people who receive those benefits to work. Those with children 13 and under, people with disabilities and seniors are not subject to the new work requirements.
The new rules also ban certain immigrant groups from receiving benefits.
The county estimates that hundreds of thousands of residents will be impacted by the new rules, that 75,000 residents could lose Medicaid benefits because of their immigration status, and another 13,000 would lose access to food stamps.
To keep up with administering the new requirements, the county estimates it would have to hire 122 new staffers, positions that would be funded by the sales tax hike.
With some of the new rules already in effect and more set to begin at the start of 2027, Montgomery Steppe has gotten her colleagues to pass legislation launching what she’s named the Safety Net Bridge program.
The program is already providing food assistance to people who have lost eligibility for CalFresh. Plans for how the county will help provide healthcare to people who might lose Medi-Cal benefits will go back to the Board of Supervisors in the coming weeks.
So far, the county has held five food distribution events under Montgomery Steppe’s program.
About 1,300 people have received food at those events, said Aaron Hoskins, a spokesperson for Montgomery Steppe.
“My goal really is for the county to truly have skin in the game,” Montgomery Steppe said. “We want to keep the county of San Diego a place where we are able to take care of our neighborhoods when the federal government says it’s no longer going to care for our most vulnerable community members.”
On the sales tax hike, Alessio acknowledges that the county faces a big hole in its budget because of the federal government, but counters that the county has not been a good steward of the money it does control.
The candidate also supports new work requirements for CalFresh and Medi-Cal, arguing that “it’s not hard to apply for a job and show that you’re trying to apply for a job.”
“We live in a very unaffordable area and state,” Alessio said. “Do we want to blame the president? Do we want to blame the governor? I don’t really care who we blame, but we cannot ask normal people to absorb this sales tax hike forever.”
Financial advantage
There’s another difference defining the two campaigns: fundraising.
This cycle, Montgomery Steppe’s campaign has raised $116,000, according to campaign finance disclosures.
For Alessio, her campaign has raised about $8,500.
“I’m not pushing as a hard fundraiser on this campaign,” Alessio said. “I think that there’s too much money in politics.”
Those figures are a far cry from what was seen in the last two races to represent the district.
When Montgomery Steppe was first elected in 2023, her campaign had raised over $220,000.
Her Republican opponent, conservative activist Amy Reichert, raised $227,000.
Similar totals were seen in the 2022 contest between Fletcher and Reichert, with both campaigns raising hundreds of thousands of dollars.
But neither race was close, a sign of the waning power of Republicans in county politics. Montgomery Steppe won 62% of the vote and Fletcher won 65%.
Republicans have been handed other losses in their recent attempts to regain seats on the Board of Supervisors, a panel they had dominated for decades.
In 2024, former San Diego mayor Kevin Faulconer lost his bid to unseat Democratic Supervisor Terra Lawson-Remer. Chula Vista Mayor John McCann, a Republican, also failed to win a seat for his party last year, losing to Democrat Paloma Aguirre in a race to fill the vacancy left after the resignation of former supervisor Nora Vargas.
Read more Transformative or ‘bad policy’: San Diego County sales tax debate grows as race heats up
