Before the Trail

How a Chain-Smoking Lobbyist Made My Career and Ruined My Life

I didn’t plan any of this.

I grew up on the Eastern Shore of Maryland, the son of blue-collar parents who believed in hard work and loyalty, not résumé-building or career strategy. College wasn’t something anyone expected from me. It was a leap of faith; somehow, I made it work. I was the first in my family to go, and the first to finish. What came next wasn’t part of any blueprint. There was no master plan, no five-year goal, just a series of opportunities, gut decisions, and wrong turns that somehow ended up pointing in the right direction. At the time, it all felt random. Looking back, it almost feels like it was supposed to happen exactly that way.

I still remember the first time I met Mark Sanford. I had no clue I’d end up as his Chief of Staff or be part of an international political scandal that would plaster my name across cable news fifteen years later. That wasn’t in the cards, and to be honest, it would be another couple of years before I even went to work for him. And that only happened because I got fired and someone took my call at just the right moment. We’ll get to that later.

And here’s the thing. It’s still like that. My career has never followed a clean, predictable line. It’s been built on unexpected chances, people willing to take a risk on me, and decisions that felt more like cliff dives than calculated moves. There’s no single storyline to wrap it all up neatly, but there is a thread that has run through every chapter. Service, trust, and stepping in (or stepping up) when it matters, even when it’s messy.

If you’re looking for the version of this story that people tend to ask me about, the one that leads to the headlines, I have to rewind and start at the beginning. Not with the scandal, but with the first job that brought me to Washington and taught me how the place actually works.

---

My First DC Job

After college, I knew I needed to be in D.C. I’m not going to say politics was some lifelong dream. I wasn’t the kid who idolized Capitol Hill. But I wanted to be part of the conversation about where the country was headed. At the time, I was married and had a kid, so there wasn’t a lot of wiggle room. I didn’t have the luxury of internships or time to bounce between jobs. I needed something real. I ended up taking a job at Citizens Against Government Waste, working in media and government relations.

It wasn’t glamorous, but it was solid. I wrote press releases, tracked legislation, delivered letters to congressional offices by hand, and when needed, I filled in at the front desk as a backup receptionist. I did whatever needed to be done. It was one of those classic entry-level jobs that teaches you how the sausage gets made, and like a lot of people who come to D.C., I was paying my dues without really knowing it.

My starting salary was $44,000 in 2025 dollars, at the very low end of Capitol Hill pay today. What’s worse, I had to live on the Shore and drive 90 miles to work, one way. That’s not a made-up “in my day story.” I did that for ten years and three cars.

---

Not Your Average Joe

My boss at CAGW, Joe Winkelmann, was a real character. He had spent twenty years at the National Restaurant Association, the other NRA, and was a Vietnam vet with a short fuse, a chain-smoking habit, and a Jaguar that technically belonged to his wife’s travel agency. You always got the sense that he was five seconds away from losing his temper, and you didn’t want to be in the blast radius when it happened. We used to joke that he probably snapped a few necks back in the day, and while that was a joke, I once saw him throw a stapler and hit a coworker square in the leg. It became office legend.

He insisted on drinking at lunch and made us go to Mr. Eagen’s every Tuesday, a little hole-in-the-wall Irish Pub on Connecticut Avenue that served, in Joe’s opinion, the best shepherd’s pie in the District. And yet, for all his rough edges, Joe had an uncanny ability to spot people who would grind when things got hard. When he hired me, he pulled me aside and said, “I wanted you. The rest of those kids interned at their daddy’s law firms. You worked through college to make it. F**k those guys. They’re all going to be just fine.”

You don’t forget moments like that.. Joe had plenty of flaws, but I would’ve run through a wall for him after that.

---

The Smartest Guy in the Room

Not long after I started, Joe brought me along to my first Capitol Hill reception. It was one of those schmoozy meet-and-greets, hosted by the Texas State Society in the courtyard of the Rayburn Building. Here's a quick breakdown for those who haven’t spent time navigating the House office buildings. There are three of them, Cannon, Longworth, and Rayburn, each named after former Speakers. Rayburn is the newest and by far the most confusing. It’s a maze of long, identical hallways; delivering letters there could save half your day. Everyone hated it. So we’d split it up so that one person did Rayburn and the other did Longworth and Cannon, and you still never wanted to do Rayburn.

So we’re driving to the Capitol, and Joe decides to hit me with a little life advice.

“Scott, do you know who the smartest guy at every reception is?” he asks, taking a long drag from his cigarette.

I said, “No, who?”

He replied, “The guy who’s not drinking. That guy doesn’t say anything stupid, he remembers every conversation, and he never wakes up wondering if he screwed something up.”

Made sense to me. I wrote it down like it was the smartest thing I’d ever heard.

We got inside, slapped on our name tags, and Joe immediately headed to the open bar. Naturally, I followed.

“I thought the smartest guy in the room doesn’t drink,” I said, a little confused.

Joe grinned, ordered a highball, and said, “That’s right. And tonight, you’re going to be the smartest guy in the room.”

For whatever reason, that moment stuck with me. I wasn’t a heavy drinker to begin with, but from that point on, especially at professional events, I kept it clean. Club soda with lime. That simple rule probably saved me from more than a few career-ending mistakes.

---

Gotta Catch ’Em All

After the 1994 Republican Revolution flipped the House and brought in a flood of new members, Joe saw an opening. One day, he called me into his office and gave me a very specific assignment.

“Every week, I want you to walk into ten congressional offices, introduce yourself to whoever’s sitting at the front desk, hand them your card, get theirs, and talk to them. Find out where they’re from, what they care about, and what sports team they follow. Anything.”

He told me the front desk person is the gatekeeper. If they like you, they’ll let you in. If they don’t, you’ll never get past that front door.

I took it seriously. Every week, I hit those offices, made conversation, and collected business cards. A few weeks later, Joe followed up. I showed him my stack and gave him a quick briefing on what I’d learned.

“Good,” he said. “Now go back and ask to meet someone on the legislative team. Start a conversation about a bill. Learn their names, get their cards, and add those to the list.”

Before long, I had two full Rolodexes on my desk and probably knew more Hill staffers than most junior lobbyists. Joe pulled me aside again and gave me what might be the most useful piece of advice I’ve ever gotten in Washington.

“There’s a thinning out process on the Hill. Some people burn out and leave after a year. Some people stick around and rise. Staff assistants turn into LAs, then LDs, then Chiefs. If you keep that Rolodex up to date, treat people with respect, and keep showing up, it’ll be the best investment you ever make.”

I didn’t fully grasp it then, but Joe wasn’t just teaching me how to network. He was teaching me how the game works. He also laid out the path for the rest of my career.

---

What’s Next

Next time on Political Hangover, I’ll tell you about the moment it all came crashing down, how I got fired, and how one of those business cards I picked up during those early days saved me at exactly the right time. It also set me on a course with the Appalachian Trail.