Today we’d like to introduce you to Drew Willey.
Hi Drew, thanks for sharing your story with us. To start, maybe you can tell our readers some of your backstory.
If you told me ten years ago that my courtroom battles would evolve from defending people accused of crimes to fighting billion-dollar appraisal districts over commercial property valuations, I probably would’ve laughed. But here we are—and honestly, the overlap is uncanny. Both systems are massive, technical, and stacked against the little guy. And in both, the key to winning is having someone who knows how to fight smart inside a complex system.
I started my career as a criminal defense attorney here in Houston, where I co-founded Restoring Justice, a nonprofit that provided free representation to people who couldn’t afford a lawyer. At the time, Harris County was (and still is) one of the largest drivers of mass incarceration in the world—our jail population hovers around 10,000 people, second only to Los Angeles, and Texas leads the nation in prison population. Through Restoring Justice, our team prevented more than 600 years of incarceration, saved tens of millions of taxpayer dollars, and helped shift the entire county’s indigent defense system toward fairness and reform.
That experience shaped how I practice law: I learned how to take complicated, entrenched systems and turn them into fair fights. Over time, I realized that commercial property owners face a similar imbalance—this time in the world of property tax. Every year, appraisal districts across Texas (and beyond) issue aggressive valuations that can make or break a company’s bottom line, potentially putting real people’s jobs at risk. And just like in the justice system, the process can feel impossible to navigate without someone who knows how to stand their ground.
That realization led me to join Gray, Winston, & Hart as a Senior Attorney, where I now focus almost exclusively on commercial property tax litigation across Texas, Colorado, and New Mexico. The firm’s reputation for high-stakes litigation fits perfectly with my trial background—I’ve spent over a decade in Texas courtrooms, and I bring that same level of advocacy, strategy, and grit to every valuation fight.
But I haven’t left the justice work behind. I still take on selective civil rights and indigent defense cases, and recently represented unsecured creditors in the Wellpath bankruptcy, one of the largest healthcare-related restructurings in the country—holding a billion-dollar prison healthcare provider accountable to those it harmed. Today, I just support that same fight for fairness in a broader way—using the courtroom to protect both people and property, and to make sure every client, no matter their context, gets a fair shot.
Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
Not even close—but I wouldn’t trade the road I’ve been on for anything.
My early years were spent in some of the hardest corners of the legal system—working with people experiencing chronic poverty, mental illness, and trauma, many of whom society would rather forget. Through Restoring Justice, we didn’t just provide courtroom advocacy; we offered intensive counseling, social support, and holistic services to help clients rebuild their lives from the ground up. It was incredibly meaningful work, but also emotionally exhausting. There were days it felt like swimming upstream against the entire current of mass incarceration, trying to hold hope in a system designed to drain it. I saw firsthand how the system can wear down even the most determined people.
When I stepped back from that world to focus on building a new practice, it wasn’t easy. In a lot of ways, I was starting over—new clients, new industry, new reputation to build. There were moments of doubt about whether I was leaving behind what I was “called” to do. But over time, I realized I wasn’t leaving the calling—I was living it differently.
Building a property tax litigation practice has its own kind of challenge. It’s technical, data-driven, and fiercely competitive. Every case is a chess match between appraisal districts and property owners, with millions of dollars at stake. But I’ve found real purpose in it. The courtroom strategy, the negotiation, the collaboration with consultants and valuation experts—it’s all the same craft I’ve honed my entire career, just in a new arena that rewards preparation, clarity, and bold advocacy.
So no, the road hasn’t been smooth. But the rough parts shaped how I practice now—with more empathy, more strategy, and more appreciation for the people and companies who trust me to fight for them.
Great, so let’s talk business. Can you tell our readers more about what you do and what you think sets you apart from others?
I recently joined Gray, Winston, & Hart, a firm known for high-stakes litigation. It’s a team that includes trial-tested attorneys who thrive in complex, high-value disputes—and my focus within the firm is court-room, trial support.
What we do is pretty simple at its core: we help commercial property owners with consultants and attorneys to challenge unfair property tax valuations. When an appraisal district inflates a property’s value, we step in to make sure our clients aren’t overpaying what they shouldn’t owe. That can mean millions of dollars in savings, but it also means leveling the playing field against systems that can feel impossible to navigate.
What sets Gray, Winston, & Hart apart is that we don’t just negotiate—we litigate. Many firms handle property tax protests, but few take them all the way through discovery, depositions, and trial. That’s where our strength lies. We bring the courtroom firepower of seasoned litigators to every valuation dispute, so appraisal districts know our clients are ready and able to fight for a fair result.
For me personally, that’s where my role as a Senior Attorney fits perfectly. I’ve spent more than a decade in Texas courtrooms, and that trial experience translates directly into how I handle these cases—strategically, thoroughly, and with confidence.
Brand-wise, what I love about Gray, Winston, & Hart is that we’re quietly elite. We’re not loud marketers. We’re known because we win, because we prepare relentlessly, and because we treat every client relationship as a long-term partnership. Whether it’s a hotel portfolio, energy company, or commercial development, we bring a level of trial readiness and precision that gets results.
At the end of the day, our work is about protecting what people have built. I’m proud to be part of a team that not only understands the numbers but knows how to turn those numbers into justice—one case, one property, and one courtroom at a time.
Are there any apps, books, podcasts, blogs or other resources you think our readers should check out?
I’ve learned that being a great lawyer isn’t just about knowing the law—it’s about how you think, listen, and build systems that make justice and fairness possible.
I’ve always had an interest in how technology can improve legal work. I served on the advisory board of a legal tech startup that was later accepted into Y Combinator, helping it grow from a prototype to a product used by real law firms. That experience deepened my commitment to innovation in the profession. More recently, I built “Know the Code” on my firm’s website—a searchable, AI-powered tool that helps property tax professionals and attorneys navigate the Texas Property Tax Code more easily. It’s been exciting to see how technology can simplify complexity in ways that serve both lawyers and clients.
One book that’s deeply influenced me is Redeeming Heartache by Dr. Dan Allender and Cathy Loerzel, which explores how our suffering often reveals our purpose. It resonated with me because so much of my career has involved working in heavy spaces—whether in criminal justice or high-stakes litigation—and finding meaning and growth within them.
And then, there’s my family. My wife, Jessica, and our kids are the grounding force in my life. We talk about courage, justice, and imagination a lot in our house—usually somewhere between a soccer game, a bedtime story, and a hike in the mountains. That’s what keeps me centered and creative, and it’s where I find the perspective that carries into every courtroom I walk into.
Contact Info:
- Website: https://www.graywinston.com/
- Linkedin: https://www.linkedin.com/in/andrew-willey-95590016/
- Other: https://fearlesslove.substack.com/
