When Kevin Wolff appears on my computer screen, I get a glimpse of his much-talked-about hat collection on the wall behind him. It’s vast and expertly arranged from light to dark colors, Brooks Brothers-style.
The only hat missing is the metaphorical one he wears as Bexar County’s Precinct 3 commissioner.
“I have always been follically challenged, as we see here,” he says lifting his felt hat in gentlemanly way. “For me, that is first a tool, and second, a fashion statement.”
The eldest son of County Judge Nelson Wolff is drawing closer to the end of his third and final term on Bexar County Commissioners Court. Last year, the younger Wolff told reporters he wouldn’t seek re-election after nearly 15 years in elected office, an announcement that shakes up his family’s political legacy.
In January, when Commissioner-elect Trish DeBerry is sworn in as his successor, Wolff will return to the private sector. Indeed, the Republican tells me he never intended to leave it for as long as he did.
Politics, nonetheless, is in Wolff’s blood. As our interview unfolds, he explains how his look and political prowess were inspired by the styles of both Harry Truman and Lyndon B. Johnson, two U.S. presidents he says are historically underrecognized.
“What I saw out of those two and other presidents is not so much about doing this party line or that party line, but more about doing the business of actually getting the government to run,” he says. “LBJ was a master of legislation and politics, especially at the federal level.”
Wolff’s lessons in statesmanship came early.
When he was 5, his dad — a Blue Dog Democrat — won a seat in the Texas House of Representatives. In later years, he watched his father become a state senator, a city councilmember, and in the early 90s, mayor of San Antonio.
Wolff, however, decided against following in his father’s footsteps, instead pursuing a career in the corporate world, where he thrived for more than two decades.
In 2002, Wolff’s “service ethic” kicked in after three members of San Antonio City Council were charged with bribery.
“[That] was the straw that broke this camel’s back,” he says. “This is my hometown [and] here are these people messing it up.”
For Wolff, running for council’s District 9 seat became an act of moral necessity. He left his $300,000 a year position as the chief operations officer at First American Title for a servant-leader position that paid $20 a week.
He planned to serve two terms then jump back into the corporate world. However, after his council tenure, he set his eyes on the Precinct 3 seat on the Commissioners Court, one physically — though not politically — to the left of his father’s. Since 2009, the pair have often been in opposition on political issues, which the younger Wolff chalks up to different life and career experiences.
I ask him what it’s like working with his father on such a public stage.
“So, while Dad and I have what I’ll call usually a fun time in regard to arguing [about] things that are happening at the federal or even state level, we really don’t fight a whole lot on the local level,” he explains. “Simply because when you look at local elected positions and local politics, you’re doing what I call the nuts and bolts of government.”
Wolff describes himself as a “rational Republican,” a position that comes with political challenges, especially in the Trump era.
“The more middle you get, the more your pain increases, certainly more at the federal level,” he says. “Because you don’t only get beat up by the other side you get beat up by your own side. [You] get tired real quickly [of] having the crap beat out of you by both sides, and that’s unfortunate. I see that as the biggest current downfall of our overall governmental system. Over the past 15 years that I’ve been in office, I’ve seen that gap widen and deepen, and that concerns me.”
Few elected officials leave political life unscathed; Wolff is no exception. In July 2016, he made headlines when he was charged with driving while intoxicated.
“Obviously, that was a very, very difficult time for me and my family,” he says, adding that he learned important lessons from the incident.
Not seeking re-election was a gradual decision, one he discussed with his wife Sandi and his daughter Sydney over a six-month period.
“Once, we had finally decided, it was a great relief,” he says. “I don’t know how else to explain it. You don’t realize how much you think about something until you don’t have to think about it anymore.”
Although Wolff isn’t exactly sure where he’ll work next, he’s hopeful he’ll locate a good match for his talent and experience. In the meantime, he’s relaunched his consulting work, which he started before entering public life.
“I will miss being able to do the job,” he says. “Because you can get some really good things done, especially in local government.”
Wolff, who focused on transportation issues during his time in office, ticks off some of his accomplishments, which include adding the San Antonio area’s first high-occupancy vehicle highway lanes. Those, he says, are lasting rewards for his time in public office.
He pauses for a moment, then smiles.
“You know, on a personal note, I’m probably going to miss working with Dad,” he adds.
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