Trish DeBerry‘s alarm was going off. Home late after a campaign event the previous night, she had planned to get up early and work out.

“I was kind of coherent, meaning I could hear the TV, and then I hear, ‘Trish DeBerry would walk across hot coals. She’s so desperate to be county judge.’ I was like, ‘Am I dreaming? Or did I hear that?'” said DeBerry, who flipped on the light and hit rewind.

What DeBerry heard was part of a political ad paid for by a dark-money group called Friends of Bexar LLC that reportedly bought more than $250,000 worth of TV time to attack the Republican candidate for Bexar County judge, beginning late last month.

“Yep. I wasn’t dreaming. This is where we’re at,” DeBerry said.

The 57-year-old DeBerry is now in the final weeks of an uphill campaign against longtime family court Judge Peter Sakai to win a county judge seat only one other Republican has ever held.

Her bid to replace retiring Bexar County Judge Nelson Wolff, who has held the seat since 2001, comes as Republicans’ hopes for big wins in the 2022 midterm election have faded in recent months. And she’s battling in a county so blue it favored 2020 Democratic U.S. Senate challenger MJ Hegar, a nine-point loser statewide, by 12 percentage points and Joe Biden by 18-plus points over Donald Trump.

“Partisan politics is tougher than it used to be,” said Cyndi Taylor Krier, Wolff’s predecessor and the first and only Republican to be county judge.

Indeed, DeBerry is finding the race very different from her past political experience.

She gave up a hard-fought seat on the Commissioners Court after just 11 months to file for the county judge race minutes before the filing deadline, when just one other candidate had signed up to run. She defeated Nathan Buchanan, a conservative activist and former perennial candidate for constable who raised less than $2,000 for his campaign.

The dark-money ad is just one in a series of attacks — many of which she considers sexist — that DeBerry has weathered in this campaign, even as she has tried to focus on policy proposals such as relocating the county jail and leveraging existing local public health resources.

And despite decades of working closely with members of both parties in Bexar County’s tight-knit political community and encouragement from leaders on both sides to run, few allies are now standing up for DeBerry in the final weeks of a race many Republicans think is out of reach.

“I thought we were going to get past that after I got through the primary, where I was called a drunk, a two-bit whore. Why wasn’t I married? She must be lesbian. I mean, stupid stuff,” DeBerry said of attacks from fellow Republicans in the race for the party’s nomination for county judge.

As the race comes down to the final weeks, DeBerry has held her own against Sakai when it comes to fundraising. Campaign finance reports covering July 1 through Sept. 29 indicate she raised $241,000 to Sakai’s $284,000. DeBerry heads into the final stretch with $169,000 on hand, including a $50,000 personal loan she made to the campaign on Sept. 28. Sakai reported $239,000 on hand as of Sept. 29.

And she plans to defend herself against the attacks with “a significant buy” of TV advertising beginning next week, she said Friday.

A taste for politics

Born and raised in San Antonio, DeBerry graduated from Trinity University and went on to pursue a decade-long career in broadcast journalism. She later pivoted into public relations and was recruited to manage the successful mayoral campaign of Ed Garza in 2001, despite having almost no prior political experience.

In an interview between campaign events last week, DeBerry said Garza approached her for the job because of her background in communications. She was hesitant to take on the role, but ultimately decided it would be a learning opportunity and took a leave of absence from her PR firm to do it.

“I wasn’t married, I didn’t have kids, and it was 24/7,” DeBerry said of the campaign. “As it turns out, it was one of the best experiences of my life.”

“I think if you work in politics, whether you’re consulting in politics or whether you’re a candidate, it takes a unique skill set, a special person to be able to do it just because it’s so intense,” she said. “Either you really love it or you learn very quickly, ‘I want to get the hell out of here. I’m not made for this.’”

Eight years after working on Garza’s race, DeBerry launched her own campaign for mayor, finishing a distant second behind Julián Castro in a field of nine candidates.

“My first fundraiser when I ran for mayor, we had 25 people,” DeBerry said of her campaign, which she launched with just five months to go until election day. “The last fundraiser I had was at [former AT&T CEO Ed Whitacre Jr.’s] house … and we probably had 200 people were there, so there was momentum, I just felt like we ran out of runway because I decided I was going to get in the race too late.”

Though she was encouraged by that first race, DeBerry said when she and her husband divorced two years later and she became the primary caregiver for her children while running her own PR firm, politics got put on the back burner.

Late to the party

DeBerry didn’t reenter the political arena until 2020, when she joined the race to replace Republican Kevin Wolff on Bexar County Commissioners Court. She faced a field of eight candidates in the GOP primary, vying for the traditionally Republican Precinct 3 seat.

“I just felt like the government doesn’t make it easy to be a small business owner,” said DeBerry. “And so for that reason, as a fiscal conservative, I felt like running on the Republican ticket was right for me.”

Trish DeBerry, left, and former Pct. 3 commissioner Kevin Wolff stand for a photo during a 2020 campaign event.
Trish DeBerry, left, won the Precinct 3 Commissioners Court seat previously held by Kevin Wolff, pictured here at a 2020 campaign event for DeBerry. Credit: Scott Ball / San Antonio Report

After finishing second in the primary, DeBerry went on to defeat former judge and former Bexar County District Clerk Tom Rickhoff in a runoff for the GOP nomination.

“The environment and politics today, especially in primaries, is very toxic, very combative,” DeBerry said. “You may find yourself in alignment really more in the middle, but if you don’t subscribe to the extreme, then you’re not a Republican. And so that was hard.”

DeBerry easily defeated family lawyer Christine Hortick in the general election and quickly became an outspoken member of the Commissioners Court.

She picked fights with Sheriff Javier Salazar over staffing shortages at the jail, rallied support for lowering the property tax rate and endeared herself to many in the business community as the lone Republican on a court run by Democrats.

During her tenure on the court, DeBerry’s PR firm continued to accept county contracts. Though she promised to divest from the business, she didn’t sell the firm for three months after taking office — an issue that’s figured prominently in the attacks against her during the judge race.

A direct mail ad paid for by a group called Patriots Lead Inc. depicts DeBerry’s head atop an animated Winnie the Pooh who gets his head stuck in a honey pot, suggesting she’s “gotten rich from government contracts” and still has not fully divested from her old firm.

“The attacks are baseless, at this point, and unwarranted because I fully divested myself from the company and sold it to [new owner Anamaria Suescun-Fast] in July,” DeBerry said of the firm formerly known as the The DeBerry group, now called TalkStrategy.

Though DeBerry continued to work there while serving on the Commissioners Court, DeBerry said she didn’t have to recuse herself from any votes due to conflicts of interests with her business.

“I took a back seat [at the firm], said I was only going to work on private accounts, I wasn’t going to work on any government contracts, and we were never awarded any government contracts when I was a county commissioner,” DeBerry said.

‘Very, very savvy’

When Wolff announced plans to retire, most Republicans were skeptical of their chances in a county Republicans haven’t won since Gov. Greg Abbott was on the ballot against Wendy Davis in 2014.

“Given changing demographics and voting patterns, any countywide Republican candidate faces an uphill climb,” said Republican political consultant Kelton Morgan, who worked for a moderate Democrat, Ina Minjarez, in the county judge primary and runoff.

But gubernatorial election years have historically offered Republicans their best prospects in Bexar County, and DeBerry was eager to capitalize on what she saw as a potentially good environment in the 2022 midterm election. President Joe Biden’s approval was lower, gas prices were higher, and the Supreme Court had not yet overturned Roe v. Wade.

“She became convinced that it was easier to find someone else to fill [the] commissioner Precinct 3 [seat] than it was to find someone to run for county judge,” said Krier, who talked to DeBerry before she entered the race.

Outgoing Bexar County Judge Nelson Wolff, left, with then Bexar County Precinct 3 Commissioner Trish DeBerry, center.
Outgoing Bexar County Judge Nelson Wolff, left, with then Bexar County Precinct 3 Commissioner Trish DeBerry, center. Credit: Scott Ball / San Antonio Report

Without the built-in draw of a presidential race, a midterm candidate from either party must rely on enthusiasm from their base, with whom DeBerry’s relationship has been complicated.

Over the summer DeBerry said she backed out of a campaign event hosted by local GOP precinct chairs when supporters of the Jan. 6 insurrection were added to the speaker lineup.

But San Antonio developer David Starr hosted a recent fundraiser for DeBerry with former Republican presidential adviser Karl Rove, Abbott endorsed her on Tuesday and Republican Party of Bexar County Chair Jeff McManus praised her tireless work ethic on the campaign — all signs that the party has embraced DeBerry in spite of her sometimes spirited differences with the GOP base.

“Trish DeBerry is a fighter who is ambitious, tenacious, and has great vision for the county,” McManus said. “She’s a very, very savvy person.”

Changing environment

Still, the political environment also has made it hard for DeBerry to play up what she sees as her biggest strengths in the county judge race: her strong interest in county policy and willingness to bring forward out-of-the-box solutions to address longstanding problems.

Though Democratic and Republican operatives both say Republican candidates have had success focusing on national issues like crime and cost of living increases this election cycle, DeBerry has instead focused on her experience and ideas.

Throughout many debates and candidate forums, DeBerry has used her time to tout ideas for moving the county jail to promote development on the West Side, addressing the reliance on overtime to staff the jail and merging the city and county’s health systems.

Meanwhile, moderate Republicans across the country are up against a Democratic Party that wants to tie them to GOP’s most extreme elements.

“One of the local Democratic strategists cornered me in a restaurant and asked me why I want to support this ‘right-wing extremist’,” Trip Pilgrim, a friend of DeBerry’s who shares her moderate political views, said. “It’s the narrative of, ‘Let’s push her to the furthest right that we can,’ which is not who she is.”

Shadowy group

Little is known about who was behind the ad that ran on local TV stations claiming DeBerry was “desperate” to become county judge in order to enrich herself.

The group Friends of Bexar County used a corporate filing service to register as an LLC last month in Delaware with few identifying details; its website has since been removed. Texas law requires that a group that spends more than $920 must register as a political committee and file regular reports of its campaign contributions and spending, said Texas Ethics Commission Executive Director J.R. Johnson. Failure to do so can result in criminal and civil penalties.

So far no such registration or reports have been found for Friends of Bexar County, and DeBerry said she has filed a complaint with the ethics commission, the first step required to trigger an investigation.

Cyndi Krier
Cyndi Taylor Krier, former Bexar County judge

Advertising agreements between the dark-money group and two local TV stations list Juli Branson as Friends of Bexar’s executive director. Branson has longstanding ties to Republicans, including former U.S. Rep. Lamar Smith, according to the San Antonio Express-News. DeBerry said Smith called her to say he had no connection to the ads or to Branson.

“These aren’t real issues where you can be for or against it,” Krier said of the dark-money ads that ran against DeBerry. “She’s ambitious? I mean, give me a break. She would crawl over hot coals? That is mean and without foundation, and made to draw attention and to create impressions on which there are no facts to base.”

After the TV attack ad aired, DeBerry called a press conference to accuse — without offering evidence — personal injury attorney Thomas J. Henry and prominent ad agency leader Bob Wills of being behind the ad. She also alleged Sakai knew about the ads. All three denied any involvement.

A few days later she turned to Sakai at a debate hosted by the North San Antonio Chamber.

“You’ve said for 26 years that you stand up for women and you stand up for children,” said DeBerry, referring to her opponent’s decades as a children’s court judge. “I’m asking you today to stand up for women who run for political office, because this is not right.”

In a nod to the rapidly shifting tone of the race, Sakai, who just months ago suggested there was little difference between him and DeBerry as candidates, flatly rejected her plea. 

“What I hear you say is you’re questioning my integrity, you’re questioning my character, and you’re questioning my reputation,” Sakai responded. “I have stated openly on the record that I’ve had nothing to do with that ad. … I am not going to repudiate something that I have nothing to do with.”

Bexar County judge candidates Trish DeBerry, left, and Peter Sakai participate in a forum hosted by the Real Estate Council of San Antonio at the Petroleum Club on Wednesday.
Bexar County judge candidates Trish DeBerry, left, and Peter Sakai participate in a forum hosted by the Real Estate Council of San Antonio at the Petroleum Club in September. Credit: Nick Wagner / San Antonio Report

DeBerry has pledged to keep searching for the source of the ad, and stands by her decision to keep talking about it.

“I’ve had plenty of phone calls from people, I have plenty of texts from people [expressing support], but you know if I stand up there and I can’t name the source associated with who’s responsible for it, I mean, that’s challenging,” DeBerry said.

Driving the conversation

Despite the recent turn the campaign has taken, DeBerry has no regrets about her decision to seek the county’s top job.

“The hardest part for me was having to resign my [county commissioner] seat because I loved the seat,” DeBerry said. “I worked hard for it. And I thought I was really incredibly effective at it.”

DeBerry said she’s spent the last seven months hitting multiple campaign events per day. Win or lose, she believes she has influenced the race, leading to a more substantive conversation on the issues.

“If no Republican had stepped up, would Peter really have had to frame the kind of platform and talk [about] the things he’s talking [about] today? … No,” DeBerry said.

If she’s successful, DeBerry will oversee a record $2.8 billion budget and have the opportunity to steer the county government in a new direction after Nelson Wolff’s long tenure.

If she loses, DeBerry, who lives in Alamo Heights, said she will likely go back to the private sector, where she can perhaps put some of recent experiences to use.

“I’ll go into consulting, whether it’s crisis communications consulting or some other [form],” DeBerry said.

“Or,” she added, “I may do something totally different.”

Andrea Drusch writes about local government for the San Antonio Report. She's covered politics in Washington, D.C., and Texas for the Fort Worth Star-Telegram, National Journal and Politico.