For Dwain York, you might say the gravitational pull towards education was strong. It began teaching mathematics and coaching football in the high plains of West Texas and eastern New Mexico, made a short detour through the Permian Basin oilfields, and took root 25 years ago in the Wimberley Valley.
York began his career in public education as a secondary math teacher, head varsity football coach, and athletic director. But in 1980, with oil prices soaring, a friend convinced York to take a much more lucrative job in the petroleum business. A mathematics major, he took a desk position in Midland preparing work orders to improve oil well production. On this particular day, he was making his first drive out to the oilfields to present his recommendations.
“I’ve never been out there, and I’m in a shirt and tie, and I show up with this nice typed-up work order,” York remembers. “The foreman comes in and he’s in his jeans and boots and cowboy hat and I’m sitting there telling him what needs to be done to his wells. And then he asks me if I’ve ever been on a platform. I say no. Do you know anything about pump jacks? Nope.”
“And then he says ‘when is the regional office ever going to understand that if they just let me do my job instead of sending guys like you out trying to tell me what to do?’ I said yes sir, and I just left,” says York.
It took a couple more experiences in the oil business - including a harrowing helicopter ride to an offshore oil rig and some dangerous fracking episodes - to convince York that the oil business wasn’t suited for him.
Because York had coached football and basketball before his stint in the oil patch, he quickly landed a job as a high school math teacher and coach in Eunice, New Mexico. After accepting an offer that he couldn’t refuse to coach the girls basketball team, the program went from dismal to a playoff contender. During that time, York learned that the dynamics of girls basketball were much different than varsity football.
“I wouldn’t stay seated, and I was constantly getting a technical because my voice carries so bad,” York says. “So when I started getting agitated, my student manager learned to tug on my jacket and hand me a peppermint, and that was my cue to sit down and shut up.”
To this day, that student manager from Eunice is still on York’s team. Michelle Warren has spent her last 16 years as a counselor in the Wimberley ISD and is married to Doug Warren, the Wimberley Texans head coach and athletic director.
York was happy coaching and teaching into the late 1990s, but he would soon arrive at a crossroads. Feeling the allure of college football, he was toying with the idea of moving up in the ranks and coaching on a bigger stage. That’s when another York teammate - his wife Teresa and current Wimberley ISD librarian - offered some coaching advice of her own.
“She said let’s talk about just the family; not you, not your career. We’ve got two girls that have kind of been dragged around with your coaching jobs, and one is entering high school and another is about to be,” York says. “So I think it’s time you use your education management degree and get into administration.”
Of course, York had no experience as a principal, so he knew he was likely headed for a pay cut as an assistant principal - if he could even find someone who would take him. A short time later, Teresa had found an open position: assistant principal at Danforth Junior High in Wimberley, Texas. York says he really hadn’t heard of Wimberley, but applied for the job anyway.
After an interview process that York says was more intense than any of his athletic director positions, he got the job. “I guess I answered their questions correctly, because next thing you know, we’re moving our family here to Wimberley,” York says.
Once the new school year started, York’s daughters told their dad that they didn’t feel adequately prepared for the material that Wimberley students were tackling - expectations were that much higher in Wimberley.
“Our daughters really struggled that first year because they will tell you they really didn’t know how to study - they had never had any real homework before. It was a real eye-opener, and that’s a story I tell to parents thinking about moving here. That speaks to the quality of Wimberley schools, both academic and extracurricular expectations,” says York.
At that time, the Wimberley ISD faced difficult financial times. To exacerbate those troubles, the district was also facing designation as a “Robin Hood” district, which is one that has to pay into a state fund that goes to districts in communities with lower average property values. Adding to the chaos, the high school principal had left abruptly, and there were rumors of layoffs. York figured that since he was one of the newest hires, he’d likely be the first to be let go. Luckily, York befriended Randy Palmatier, the district’s assistant superintendent at the time.
“Randy and I really hit it off, and he became a mentor. I told him my aspiration is to be a high school principal and see where that takes me,” York explains. “So Randy convinced Marian [Strauss, Wimberley’s superintendent at the time] to give me a shot. And so the next thing you know, I’m moving over to the high school.”
The first year of Principal York was rocky at best. He was used to an athletic director’s leadership style that was “my way or the highway.” York quickly learned from a group of his school’s most respected teachers that he had to change his leadership style, and quickly.
“These pillars of the high school all sat down with me just before Christmas break. And they said listen, we’re willing to work with you, but we don’t want to work for you. And that changed my leadership style for sure,” York says. “It brought me back to my younger coaching days when another coach would say ‘hey, look, you can’t just break kids all the time and expect them to perform for you. So I took that into the classroom.”
York implemented faculty advisory meetings and listened to his staff. He began visiting band practices, attending school plays, focusing on UIL academics, and immersing himself in Wimberley High School to help him see his school from different perspectives. For the next nine years, York enjoyed his time as principal.
In 2007, the financial outlook for Wimberley ISD had grown more desperate. York says the district was $2.67 million in debt and facing potential insolvency because of inflated enrollment numbers. The school board decided that it was a time for a change in leadership, and they tapped York to lead the district as its new interim superintendent.
Almost immediately, the district initiated a $25.4 million school bond package to build Jacob’s Well Elementary and begin paying off its debts. York admits he was in way over his head, but credits his success with surrounding himself with experts who could navigate sensitive budget issues. He also says his mathematics background and his brief time in the oilfield helped him decipher volumes of spreadsheets.
While contentious, the bond package passed, and York was able to begin the long and difficult process of fixing the district’s financial problems. He also ended the district’s food service and bus contracts and brought them in-house, which saved money and made them more responsive to the needs of the district.
“Mr. York has led our district through some really tough times, going from only $200 thousand in our fund balance to $8.9 million today,” says Dee Howard, Wimberley ISD assistant superintendent. “He has been very involved in school finance at the local and state level. He has served on committees that have tried to make improvements to the way the state allocates and takes funds from districts.”
Once the debt problem was taken care of, York could focus on finding money to increase teacher salaries, which helped to slow turnover and keep valued faculty within the district. Just as he had immersed himself in his high school, he got more involved in the workings of pre-K through fifth grade. He formed cross-district leadership and advisory teams to garner input.
To increase enrollment, the district began accepting transfer students. In the first year alone, 82 students and their families enrolled in Wimberley schools, which had an immediate and significant impact on finances. Last year, approximately 375 transfer students have enrolled, saving nearly $2.7 million for the district. Those students are held to high academic, attendance, and behavior standards.
York also made it a priority to strengthen connections in the community, attending city council meetings and building relationships outside the district - something York has continued to do during his career. He credits the outreach with residents approving new bond packages in 2013, 2016, and 2018, totaling $77.4 million for facilities and land acquisition (most notably the Blue Hole Primary School), renovations, technology, and transportation.
More than anything, York credits his teachers and staff with making Wimberley ISD the premier school district that it is. York says he believes in retaining talent and promoting from within. In fact, 22 Wimberley teachers grew up as students in the district. And he adds that nearly a dozen who left the district for “greener pastures” have returned to Wimberley after a year or two.
“His leadership resonates in the teachers and employees that have been with the district for many years,” says Dottie Busby, York’s administrative assistant since 2007. “When you look at the final product, the achievements of the students from Wimberley, that should always reflect on the Administrative team and leadership.”
One former Wimberley staff member coming back home is Dr. Greg Bonewald, York’s replacement as superintendent and one of 57 applicants for the job. York was principal at Wimberley High when Bonewald was a teacher and assistant principal. He also promoted Bonewald to principal when he took the superintendent position in 2007.
“I’ve been impressed with Greg since I first got to see him in action as a teacher and a coach. I immediately received positive feedback from students about him - he was a natural,” York says. “I’ve continued to be impressed with his strong leadership as I’ve watched his career progress. He’s a man of integrity and a class act, and I’m thrilled that he’s coming back to Wimberley.”
York’s tenure hasn’t been without its difficulties. He cited the debate over allowing HEB to build on the former site of the Bowen Intermediate School and the recent trademark registration dispute over the Wimberley Texan logo - not to mention the challenges of leading teachers and students through a pandemic. It’s enough to make anyone reconsider their chosen profession.
In fact, Wimberley is one of more than 80 districts in Texas alone that is making a superintendent transition this summer. Many public school administrators have cited the pandemic as well as the increasing political and social pressures that come with the job. York downplays that, however, and says it was simply time for him to do something else.
“It was never COVID, because I think that’s a huge feather in our cap as a school district. We were the only school district that really provided face-to-face learning through all of this. We started school on time and we graduated on time. It took a toll on our kids and that took a huge toll on our teachers,” explains York. “But I wasn’t retiring for that reason. It just got to a point where, you know, it’s time for me to retire.”
So what does retirement look like for York? He has four grandchildren in the district, and he plans to watch them grow up. He’s hoping he’ll have time for more hunting and fishing. And he’s open to the possibility of consulting other districts on how to navigate intricate school finance laws. Those who know him best say he’s a quick study.
“Mr. York’s knowledge of all aspects of the district – from the school zone lights to the completion of bond construction to Texas legislation on school finance – is what I feel has made him successful,” says Busby. “He is well-informed – and if he isn’t, he will be by the end of the day.”
For his part, York says his successful career is mostly about open communication, learning quickly, and persevering.
“Most of the time I didn’t know what I was biting off until I really got into the middle of it. You just do it – you just find a way to do it. It’s no different than coaching, where you take kids and you learn what their abilities are. There’s a certain amount of trial and error but you keep working at it.”
