Regulatory Oversight Podcast — Lessons From a Senate Insider: Legislative Strategy With Jason Smith
Host: Stephen Piepgrass
Guest: Jason Smith
Aired: May 20, 2026
Stephen Piepgrass:
Welcome to another episode of Regulatory Oversight, a podcast dedicated to delivering expert analysis on the latest developments shaping the regulatory landscape. I’m Stephen Piepgrass, one of the hosts of the podcast, and I lead our firm’s Regulatory Investigations, Strategy, and Enforcement, or RISE, Practice Group. Our podcast highlights insights from members of our practice group, including its nationally ranked State Attorneys General practice, as well as guest commentary from industry leaders, regulatory specialists, and current and former government officials. Our team’s committed to bringing you valuable perspectives, in-depth analysis, and practical advice from some of the foremost authorities in the regulatory field today. Before we begin, I encourage all our listeners to visit and subscribe to our blog at regulatoryoversight.com to stay current on the latest in regulatory news.
Today, I’m joined by Jason Smith, who recently joined Troutman Pepper Locke as a member of our practice group. Jason brings a wealth of experience from Capitol Hill, and we’re going to talk about how that background shapes the strategic advice he gives our clients. Jason is a veteran Senate lawyer and strategist who most recently served as Deputy Chief of Staff and Legislative Director to Senator John Fetterman. Before that, he was Senior Counsel to Senator Patty Murray and General Counsel to Senator Mark Begich. With more than 15 years of experience on Capitol Hill, Jason has managed major legislative teams, led judicial selection in high-stakes negotiations, and advised on voting rights, judicial nominations, and crisis response at the highest levels of federal government. Jason, thanks for joining me.
Jason Smith:
Stephen, pleasure to be here on the pod and pleasure to be here at Troutman.
Stephen Piepgrass:
Absolutely. Well, we’ll dive right in. It’s been wonderful getting to know you during the recruiting process and onboarding process and now getting to work with you here in the practice group. I think our listeners would love to hear about your background, but maybe as we get started, just talk a little bit about what you’re doing right now and how you’re bringing to bear your Capitol Hill experience in your day-to-day work at Troutman.
Jason Smith:
Great. Yeah. Well, let me say one of the hallmarks of what I learned on Capitol Hill was that there are no simple problems and there are even fewer simple solutions. What I mean by that is it’s very rare that somebody has a problem that is narrow in scope and with a simple solution. And a lot of times it involves combining litigation strategy with governmental engagement, both at the legislative and executive levels, to come to a holistic outcome. So what I’m doing here at the firm is showing people how the RISE group can combine all sorts of expertise to come up with those 360-degree solutions to people’s problems. And part of that, and part of what I’ve been engaging in already, is showing lawyers what actually moves the needle in the legislative process and on Capitol Hill. And that is, there’s both a substantive element to that, and there’s also a strategic element.
The substantive element is the thing that most people think of when they think of lawyers. How does this problem get solved? What is the provision in the law that is causing me a problem? What is the regulation that is in my way? But the second part is something that typically sits in a different silo, which is, well, if the answer isn’t in a courtroom, where is the answer? And what I bring to the table is telling our clients how to get things done outside of the courtroom. Here, okay, we have a problem, and we need a legislative solution for it. Well, I think everybody’s seen that the legislative process is not working super well these days. How do you get something through? How do you even get a senator or a congressperson interested in solving your problem at all?
And that is part of what Troutman brings to the table in that we structure our solutions for our clients not just to achieve a narrow goal or a narrow judicial outcome. It is also how do we frame this properly to get the political buy-in? How do we tailor this so that it actually solves the problem that you need solved and is calibrated for success to get through? Whether that is a legislative solution, whether that is a regulator deciding to open an investigation or close an investigation, are you speaking in the language of the regulator or of the legislator? Because folks on the outside speak in a whole different world of interests and equities.
Stephen Piepgrass:
Yeah, that’s great, Jason. And I think that highlights for our listeners why you are such a great fit with the RISE practice group. Those of us who’ve been here a while know that we really set this group up in a way that was meant to bring creative solutions to our clients’ biggest issues. And we recognize that we have to tackle those issues holistically. And that means not just looking at the courtroom. Obviously, we have great litigation chops, but also recognizing that if this is an investigation, well, we’ve got to have folks with a lot of experience in the investigation space and then having the compliance capabilities to put into place compliance protocols to carry out whatever resolution we’ve ultimately reached. But then what we’ve added on to all of that is the government relations component. And why I think you fit so well with us is you are also in your practice are bringing all four of those areas: investigations, litigation, compliance, and government relations to bear in the cases that you’re handling.
Jason Smith:
Yeah. And I would tell you, Stephen, from my experience on the Hill, and I was up there more than 10 years, is I can’t tell you how many constituents, how many folks, whether those were businesses, trade organizations, or even just individuals that I would meet with who would come to me with problems. And a lot of times these folks were represented by some very large law firms, very large government affairs firms, and they would come to me with the problem, and I would say, “Okay, well, what is the solution that you’re proposing?” And they would kind of look at me with a blank stare like, “Well, Jason, that is your job to come up with the solution.” And I’m saying, “Well, wait a second. Why have you spent all this money on these lawyers and these consultants if they haven’t baked the cake for you that you need to go now sell?” And it was as if no one understood what I was saying.
So that’s what we bring here at Troutman is, there’s a lot of people who can get you into a room. Getting into a room or getting in front of the right person is only half the battle. The second part of it, and it is the consequential part, is what are you asking for, and how are you asking? Because if you are going into a regulator and you are talking about things A, B, C, when I know the regulator really cares about X, Y, Z, you’ve missed your opportunity. And if you get in a room with Senator so-and-so, and you are pitching a very deregulatory approach to solving a problem, and that’s not a senator who believes in deregulatory approaches, you’ve missed your opportunity. So it’s knowing your audience, knowing the substance. Because the other problem that I’ve seen many, many times, especially with large institutional clients, and I’m thinking specifically in the context of trade disputes.
I worked a number of international trade disputes over the past 10 years, and sometimes I would have large US companies coming in and asking for language that would not solve their problem. And I would say, “Well, why have you come to me with this specific ask?” And they’d say, “Oh, well, somebody told me,” or, “My trade group told me that this is what I should ask for.” And I’d say, “No, when you look at it, this is not what would actually get the job done.” And the reason that I could do that, for the most part, was I broke down the silos on the government side that Troutman has broken down on the private sector side. What I mean by that is this. Typically you’ve got lawyers who sit over here and they talk about only the matters in front of them or the clients that they have and they don’t see the broader picture. And then in a different building, you’ve got the strategists, the government relations people who think only about the substantive issue that has come to them on the legislative or regulatory side and not about an individual client.
So you have to break down those barriers and talk to the practitioners about, if I change this thing, how will that manifest in your practice? How will that look in a courtroom? How will that look transactionally? What burdens does that add to you? Does that put our client in a better position or a worse position? Is it a mixed bag? How do we mitigate downside? And so that collaboration and that left hand talking to the right hand is what sets apart your average representation from something that can really get you long-term success.
Stephen Piepgrass:
Yeah, that’s great. And I think really does summarize what hopefully our clients find makes us different and unique. Love to talk with you a little bit about your experience on the Hill. Obviously, I worked on the Hill for many, many years ago for several years. And I was reading through all of the different folks who you’ve worked with, and it was making me laugh because I remember the three years I worked on the Hill, I worked for three different, two House members and a senator. People move and you can move fast, especially when you’re doing great work and you’ve been in a lot of different offices and had a lot of great experience and by the time you left, you were one of the gray hairs on the…
Jason Smith:
Yeah, seriously, I have a couple.
Stephen Piepgrass:
Right, right. I think a lot of people don’t realize how much of that place is run by folks fairly recently out of college.
Jason Smith:
Yes.
Stephen Piepgrass:
And so unlike that, you actually had a long career on the Hill. So tell me a little bit about it, the different folks you worked with and what your portfolios were in your different roles.
Jason Smith:
Sure. I started out working on the Hill for Senator Mark Begich, who was a Democrat from Alaska, and then Majority Leader Harry Reid on the Democratic Steering Committee. And basically what I did was I worked within the Democratic leadership to work with the major constituent groups on the outside, whether that was business trade associations, veterans groups, the Jewish community, small businesses. And within my portfolio, I had to cultivate relationships and figure out what in the Democratic agenda needed to be adjusted to meet everybody’s needs. I was also Senator Begich’s Judiciary Counsel. Senator Begich, as a number of senators up there, was not a lawyer and did not particularly care for lawyers. As he used to say, “Lawyers always tell me what I can’t do.” And what I said to him was, “Boss, I will tell you how to do properly the things that you want to do,” which is we will find a way to get to the promised land.
So I started on the steering committee. After a year, I moved over to Senator Begich’s Homeland Security subcommittee, and as his top lawyer, everything came across my desk by the end of the day. In that role, I dealt with the Manchin-Toomey National Background Check bill, dealt with the last time that the Congress meaningfully attempted comprehensive immigration reform, and dealt with some of the highest pressure situations in that time period because my boss was a frontline member. It was always an open question whether he would be reelected as a Democrat in Alaska. And he ended up losing by about 6,000 votes, which was a heartbreaker. But it made everything that I did in that office extremely risky. If you stepped in the wrong spot and you got a press story, that could be your job, that could be your boss’s career. So it taught to me the importance of thinking first, considering all the angles, all the possible pitfalls, and then moving decisively.
You still have to move quickly because the news cycle, the legislative cycle, requires quick action, but you can’t move recklessly. So with Senator Begich, I focused a lot on voting rights as well and some of the finer points of constitutional rights. And when he lost, I went to work for Senator Patty Murray, where I handled a wide range of issues, including housing, judiciary, agriculture. There’s nothing that says agriculture like a boy from New Jersey, I’ve always said.
Stephen Piepgrass:
It’s the Garden State. Come on.
Jason Smith:
It is. I’ve heard there is a garden somewhere in New Jersey. At the time, Senator Murray was the ranking member of the HELP Committee, which is Health, Education, Labor, and Pensions. And we’ve had some things going on in the health space over the past decade. Did a lot on pharmaceutical reform, PBMs, some of the intellectual property issues. In addition to, at the time, we did a full reauthorization of the Elementary and Secondary Education Act, which was a lot of fun. In that role, I also got my hands on a bit of an oversight team, and working with my colleagues, we did a lot of really high-consequence investigations and oversight work. We looked at medical devices that were not delivering what the company had billed to the patients. And we looked at the Labor Secretary at the time, Alex Acosta, who had, in his former role as United States Attorney, been involved in the Jeffrey Epstein situation. And we asked a number of questions and would not let it go until eventually the Labor Secretary was forced out of office.
So I know from the inside, one, what draws the attention of investigators and politicians trying to do oversight work. What are they actually looking for? What is the type of responsiveness that you should provide to Congress? And how do you answer the questions? What is a legitimate inquiry and what is a fishing expedition that is meant to really just muddy up a client or an actor? And in that time, there was an awful lot of investigating to do, and it was never dull, that is fair to say. In my last role, I was Senator Fetterman’s Deputy Chief of Staff, Chief Counsel, and Legislative Director. And of course, it was the most boring role because John Fetterman is an extremely boring man. But it was fascinating, it was a lot of fun.
And I was able to lead a team that delivered just last year more than $300 million in congressionally directed spending for constituents in Pennsylvania. Things to get bridges built, get roads built, expand airport service, make sure that there’s fire and rescue in rural communities. Really important stuff that change people’s lives for the better. And also with John, I found myself in the middle of some of the most contentious, high-profile political issues that are out there, whether that is the protests that occurred on campuses following the just absolute barbaric attack on October 7th on Israel or high-profile labor disputes. I mean, we had hot strike summer, what was that, two or three years ago? And I found myself in the middle of a number of labor disputes trying to bring sides together to get deals that put people back to work and got profits flowing to the corporations. And we found success.
And the key to that was listening to both sides and rooting ourselves in principles about what we wanted to accomplish, but understanding that there was no one road that would get us to success. People have to give on both sides in different ways that they didn’t expect. And that’s a lesson that carries very cleanly into the legislative and regulatory work, which is, you may think at the beginning of the day, and I’m gonna steal a little bit from a former speaker of the House now, you may think in the beginning of the day that you’ve gotta put up a ladder and jump over a wall and that’s how you’re gonna get past the wall. But then maybe we realize the ladder isn’t high enough, we’re gonna have to blow up the wall. But then we realize that the wall is too thick, we’re gonna have to dig under the wall. And then we realize that it goes down to the center of the earth, so we’re gonna have to get a plane and parachute over the wall. But we’re gonna get over the wall. One way or another, we are getting over it.
So yeah, it was a lot of fun being up on the Hill because there were no two days that were ever the same. And the problems that were coming in from constituents were always extremely bespoke. And that experience and the joy that I got from that is something that has also carried over to our firm, which is clients are coming in with no two problems are ever the same. Because even if the root of your problem is the same, your desires and your equities and your organization’s needs are different. So it’s, “Alright, let me see what you are presenting and how do we think about this not only from a 360-degree perspective, but how do we almost turn your problem over and look at all of the angles and say, Hey, I think you missed one pathway and that might be the pathway that gets us to success?”
Stephen Piepgrass:
Yep, that’s great. Well, we are approaching the end of our 25 minutes or so here for the podcast. One of the things that you mentioned really resonated, which was talking about bringing people together, hearing both sides, coming to the right resolution. And there are so many parallels to what you were talking about with the way that we, for example, the way you helped your client, a senator who didn’t like lawyers, get what he wanted done. So I know that in-house counsel listening to this, I’m sure that resonated with them as well as they’re thinking about working with their business colleagues. But one of the things that you said was how you work to bring people from different perspectives together to get the right thing done. And that’s one of the things that I value most about our practice group.
We’ve got folks from both sides of the aisle, but we’re all really good friends and we have a common interest, which is let’s get to the best result possible for our clients and let’s also enjoy ourselves while doing so. And I think that that’s come through as we’ve gotten to work together so far. I’m really excited about the years to come getting to work with you, Jason, and it’s just a pleasure adding you to the team. And I know that our clients will enjoy working with you as well.
Jason Smith:
Well, thanks, Stephen. I very much appreciate it. And I think we are going to have a lot of fun and a lot of success for years to come. So yeah, happy to come by the pod anytime.
Stephen Piepgrass:
Great. Well, I’m sure this will not be your last visit. So thanks again for joining me today. It’s been a great conversation. I appreciate you sharing your insights and some of your story, and I know our listeners enjoyed your perspective too. Thank you too to our listeners for tuning in. Remember to subscribe to this podcast, Apple Podcasts, Google Play, Stitcher, whatever platform you choose, and join us again next time.
