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Running for Office as a Trial Lawyer

AAJ President Lori Andrus spoke with attorneys Tyler Bailey, Lindsey Cheek, Jessica Ramirez, and Stephen Skinner, all of whom have sought to win election to public office—some successfully, some not. Together, they discuss why they decided to run and how candidacy can benefit the trial lawyer community.

Lori E. Andrus September 2024

LORI ANDRUS: Trial lawyers make natural candidates for public office. We’re gifted speakers. We are often leaders in our communities. We look out for folks who don’t have a voice and help lift them up. We’re problem-solvers. All of these things are critical to being a public servant. So, let’s start with brief introductions.

TYLER BAILEY: I joined AAJ immediately after law school. When I started my practice, I became active with the Minority Caucus and the New Lawyers Division, and I participated in the AAJ Leadership Academy as well. Most of my work is in the civil rights realm. I handle civil rights and personal injury cases, and I represent a lot of crime victims in civil cases.

I also serve on the Columbia City Council in South Carolina’s capital. South Carolina is a red state, but the values of Columbia’s demographics lean more toward mine. I felt sitting on the city council would be a good way for me to serve. It means I have influence to get policy done versus fighting. I won an at-large seat in November 2023, and in January 2024, I was sworn in.

LINDSEY CHEEK: I’m a longtime member of AAJ. Originally from Houston, I moved to Louisiana almost 10 years ago to start my own firm. My firm handles cases involving cancer, asbestos, mesothelioma, and talc.

In August 2022, the Democratic Attorneys General Association (DAGA) reached out to me unexpectedly and asked me to consider running for attorney general of Louisiana in 2023. At first, I thought, “No way. I live in a red state. I have a successful law practice. I enjoy my autonomy and privacy.” But, after much consideration, I qualified in August 2023 and ran as a Democrat to be the first female attorney general of Louisiana.

JESSICA RAMIREZ: I have been an attorney for over 20 years, but I’m new to the civil law world as of 2015. Before that, I was a criminal defense attorney. I’ve practiced immigration law and many other types of law as a sole practitioner.

I am newly elected to the New Jersey State Assembly. I represent the 32nd District, which includes Jersey City and Hoboken and is one of the most diverse districts in the country. In the state legislature, I serve on the Community Development and Women’s Affairs Committee, the Joint Committee on Economic Justice and Equal Employment Opp, and the Military and Veterans’ Affairs Committee.

STEPHEN SKINNER: I am celebrating 30 years since I graduated law school. I handle consumer rights and significant injury cases. I’m an AAJ Stalwart, and I’m the immediate past chair of the LGBT Caucus. I served in the West Virginia Legislature’s House of Delegates for two terms before losing my bid for state senate in 2016.

LORI ANDRUS: Tyler, you’re a sitting city councilmember. Are you able to still practice law?

TYLER BAILEY: Councilmembers in South Carolina are part-time employees, but our work is never-ending, so, essentially, it’s a full-time job. I’m still able to practice law to some extent. Usually, I’m in the office every day. But that’s why I chose to run for city council, specifically: I have two young kids. I wanted to run and serve in a capacity that would still allow me to practice law and earn a living.

LORI ANDRUS: Stephen, tell us a little bit about your journey to becoming an elected official.

STEPHEN SKINNER: I was always interested in politics. I grew up in West Virginia, and then moved to Washington, D.C., and then New York. I intended to eventually return to West Virginia and try to do some good here. When I came back, the first thing I did was found the statewide LGBT advocacy group, and I used the advocacy group as a platform to run for the House of Delegates. I won and became, as far as I’m aware, the first openly LGBT member of the state legislature.

I was 40 years old and already established in my career. I then became very involved and moved quickly into leadership in the state legislature. Being a trial lawyer in a Democrat-majority house and senate gave me a lot of opportunities to move quickly. But then, in 2014, the Democrats lost the house in West Virginia.

I ran for state senate in 2016 and lost by a few points. In West Virginia, we’re still dealing with the aftershocks of the 2014 election. It completely changed everything here.

LORI ANDRUS: Lindsey, it was obvious to me from watching and supporting your campaign that you weren’t afraid to have fun while running for office. Tell us your fondest memory.

LINDSEY CHEEK: My fondest memories are from visiting little towns all over Louisiana for campaign rallies and events and meeting women, LGBTQ+ folks, and so many others from all walks of life who would be lined up around the corner to meet me. They were all just so appreciative that a female Democrat plaintiff attorney was running for attorney general. They knew I would take a stand and fight for them. It was wild. I would ask my campaign staff, “What’s going on? Who are they here for?” And my staff would tell me, “They’re here for you. They believe in you.” It was humbling, to say the least.

LORI ANDRUS: What was your biggest fear when you were considering running?

LINDSEY CHEEK: The scariest thing for me was wondering what would happen to me, my practice, my reputation, and my family as a result of my running for a high-profile, statewide office against a well-funded, strategic opponent. Even if you have done everything ethically possible to make sure you’ve toed the line your entire career and life, you still just don’t know what could come up or how anything you’ve done in the past could be perceived.

The solution: opposition research. I hired my own opposition team to do a thorough deep dive on me, my family, and my career several months before I qualified to run. I wanted to know everything negative that could possibly be out there so I could prepare for the battles ahead.

When my folks told me, “We didn’t really find anything,” I raised an eyebrow and told them, “Go look again, because there is no way there’s nothing out there.” I was running against a well-known GOP candidate who had a healthy head start on fundraising. I would be putting my law firm, my reputation, my life, and my integrity on the line for the world to see and scrutinize.

JESSICA RAMIREZ: My biggest fear was the unknown. I knew that I wanted to step up and run for office, but that is a scary thing to take on when there is so much unknown. That said, I do live in a blue state and was fairly confident that I would have a great deal of support behind me.

TYLER BAILEY: Columbia’s city council is nonpartisan, but everybody knows where people stand. Like most cities across America, Columbia has struggled with gentrification through urban renewal, and demographics have changed in recent years. In 2021, a Republican won the mayorship seat, and crime was up. I’m a Black civil rights attorney, and I’ve also sued police departments, so I was worried that the opposing side would use that against me and mistake my civil rights work as being anti-law enforcement. But I just leaned into it.

When people asked me if I am a small business owner, I replied, “Yes. I’m a civil rights lawyer. I have my own law firm.” The key is to be authentic and let people know where you stand. Doing that stole the thunder from those who tried to change the narrative about my work. Rather than shy away from my work, I highlighted how my legal work made me uniquely positioned to lead on certain issues.

STEPHEN SKINNER: As somebody who’s openly gay and running for election in a state with a reputation like West Virginia, I knew the opposition would focus on that. But I had prepared for how to deal with any issue related to being gay. That didn’t worry me. I feared losing. That’s a very general thing, but nobody wants to lose, and it’s a mighty motivator to do whatever you need to do to win.

LORI ANDRUS: How did you put your team together, and how long did it take you to plan and prepare to run?

TYLER BAILEY: When I ran in 2021, I had a campaign manager and a couple of consultants. We were a campaign team of six. When I ran in 2023, my campaign had two separate consultants: one for the Black side of the town, and one for the majority white side of the town. Our messaging was the same. We just phrased it differently. It helped to just cut to the center and let the people know what the issues were and what my stance was and not have demographics get in the way of a good campaign.

JESSICA RAMIREZ: The mayor of Jersey City and the state senator were really supportive. Their team knew that this was my first time running for office and that I needed a lot of support. The state senator and I essentially shared a team. I had a running mate—another assembly person—and the state senator was also on our ballot. They were both seasoned nominees. Their team was my team.

And the volunteers were amazing. They want to work with you because they just love politics. I was surprised by how people want to help. They didn’t know me well at the start, but they believed in the cause.

LORI ANDRUS: What impact do you hope to have as an elected official?

JESSICA RAMIREZ: I’m on the Military and Veterans’ Affairs Committee, and that has become my baby. My brother is a disabled veteran, and I come from a family of veterans, so I’ve always had a special place in my heart for veterans. I asked to serve on this committee, but I didn’t know how impactful it was going to be in my life. I just passed my first resolution, which is difficult to do as a freshman.

Injured workers are another area of focus for me. So many of my fellow Latino immigrants are constructing our nation, and they’re being exploited. I’m currently working on a bill regarding workers’ compensation liability.

TYLER BAILEY: In Columbia, I’m the second Black person to win a citywide election for an at-large council seat, as far as I’m aware. I want Columbia to remain a diverse city where people of all economic levels can live, work, and play and not have the city turn into one that only the affluent can enjoy. Demographics have changed significantly in Columbia in recent years. The cost of living is high. So, I want to make sure that working-class folks can still live in Columbia.

I want to fight for people. The community knows I want to fight for what’s best. I want my legacy to ultimately be: “Tyler, he’s a fighter for us. He did good for our community. He helped Columbia remain a city where everybody can live.”

LORI ANDRUS: Tyler, while you were running for office—and now that you hold a spot on the city council—have you had to shield your children from anything or take any steps to protect them?

TYLER BAILEY: I did have a security team for a while. I received death threats. I knew I needed to take safety seriously for my family’s sake. When you’re a public official, you’re a public official. People will know your address. I’ve had people show up outside my home, asking about my position on a random policy position about guns.

In a situation like that, I didn’t know what the person’s intent was—if this was an uncomfortable but friendly discussion or one that was unhinged and heading toward violence. People will say anything to you as an elected public official. With the angry ones, you don’t know if they’re making just a random threat or if there’s some real hate behind it.

LORI ANDRUS: Lindsey, will you run again?

LINDSEY CHEEK: The “trauma” of a grueling statewide campaign—and the ultimate loss—is still very fresh for me. There were a lot of missteps, disappointments, and eye-opening moments during my campaign that I am still processing.

AAJ—and especially the Women Trial Lawyers Caucus, the plaintiff asbestos litigation bar, and my fellow dragon-slaying lady trial lawyers of Women En Mass—all stepped up to support and help raise significant funds for me in a very short period of time. I will be eternally grateful for them.

If you’re going to put yourself out there and run for office—and I would love to see more trial lawyers do it—know that it’s intimidating, but it’s possible to do. I didn’t win the attorney general election, but I stayed true to myself and my values, and I’m very proud of the campaign we ran.

LORI ANDRUS: Stephen, do you think you’ll run again?

STEPHEN SKINNER: Running as an openly gay Democratic candidate in West Virginia was challenging. There may be a unique opportunity for a Democrat in the future—but I wouldn’t run for the legislature again, even if I could win because it is a quality-of-life issue for me. I live 330 miles away from the state capital. I live closer to Manhattan than I do to my state capital.

Serving in public office can be difficult on your personal life. You have to take that into account, and you have to really understand the job. If you’re a politician, you’re on all the time—you’re a part of it 365 days a year. Despite the difficulties, I didn’t think I could live with myself without running for office and trying to make a difference. I had to do it.

LORI ANDRUS: Tell us about a public servant who you admire.

TYLER BAILEY: I’ve always admired Black trial lawyers who serve in their communities. In 1970, I.S. Leevy Johnson became one of the first Black people elected to the South Carolina General Assembly since the Reconstruction era. He is also a lawyer, and he owns a funeral home. I’ve always admired people who serve as lawyers and also serve the public one way or another.

LINDSEY CHEEK: I greatly admire and am proud to call former Gov. John Bel Edwards (D-La.) a friend and mentor. He served two terms as governor, from 2016 to just this past January. He was a successful trial lawyer before he ran for governor, and few people thought he had a chance at winning in a red state like Louisiana. He pulled off a historic win, and we were lucky to have him for eight years. He had many significant achievements during his tenure, notably repeatedly vetoing tort “reform” efforts.

JESSICA RAMIREZ: I admire Annette Chaparro, who was my predecessor in the New Jersey General Assembly. She is Latina—a Puerto Rican woman like myself—who took me under her wing. She’s a class act.

STEPHEN SKINNER: Some kid fresh out of college and working in D.C. rented one of the apartments in my townhouse. We kept in touch through the years. It turns out that kid was Pete Buttigieg, who is now the U.S. Secretary of Transportation and openly gay. He’s had the career path that Tyler suggested, starting locally. Buttigieg worked on congressional campaigns, John Kerry’s presidential campaign, gubernatorial campaigns. He ran for treasurer of Indiana and was mayor of South Bend, Ind. Starting locally and progressing from there, like he did, is a great pathway because you learn raw political skills.

LORI ANDRUS: Is there any other advice you’d like to share with fellow trial lawyers who are thinking of running for office?

TYLER BAILEY: Don’t overlook local politics. City council, county council, school board, statewide. Get active in your community. Figure out who the stakeholders are. Figure out who the local consultants are. You probably don’t know who the real consultants are because, if you’re a good consultant, you’re in the background.

Figure out what your goal will be, that is, how many votes you need to win. Get an idea about fundraising. Also look at your own financial position and ask yourself if you really have all it takes to put everything into a campaign. Because if you’re running right, you’ve got to go all the way in, and there is no guarantee that you’ll win. A campaign will cost money, even at the local level.

LINDSEY CHEEK: Believe in yourself and your ability to make a difference. Even if you don’t win the election, know that you will bring important issues to the forefront and that your willingness to put yourself out there can inspire others to do the same. Speak your truth, rise to the occasion, and stay true to who you are and what you believe in, even if everyone around you is telling you otherwise.

You will learn new and surprising things about yourself, and you will do things that you didn’t know you were capable of. You will see yourself in a totally different—and very public—light, which can be uncomfortable, but it is also an opportunity to make yourself a better, more open-minded human being.

Take it all in, enjoy the ride, and know that, no matter the outcome, the day after any election, the sun will rise and set just like it always has, and you will be just fine.

STEPHEN SKINNER: Be as involved in your community as you have the capacity to be. This is not just a great place to start for business networking but also for political engagement. Make yourself the go-to person for people involved in local politics.


Lori E. Andrus is a partner at Andrus Anderson in San Francisco and can be reached at lori.andrus@andrusanderson.com.

Tyler Bailey is a sole practitioner at Bailey Law Firm in Columbia, S.C., and can be reached at tyler@baileylawfirmsc.com.

Lindsey Cheek practices in New Orleans and is the founding member of The Cheek Law Firm and can be reached at info@thecheeklawfirm.com.

Jessica Ramirez practices law with D’Arcy Johnson Day in Egg Harbor Township, N.J., and can be reached at jr@djd.com.

Stephen Skinner is an attorney with Skinner Accident & Injury Lawyers in Charles Town, W. Va., and can be reached at sskinner@skinnerfirm.com.

This article was adapted from a livestreamed AAJ panel discussion held on March 27, 2024.


VOLUNTEER TO PROTECT THE VOTE

The fundamental right to vote should ensure that every person’s voice is heard when electing the people who will represent us. But in recent years, there have been efforts to suppress voters’ access to the polls across the country. To help combat voter suppression, AAJ created its non-partisan Voter Protection Action Committee (VPAC) in 2012 to help protect the right to vote. VPAC has coordinated with national organizations to get lawyers, paralegals, and law students to volunteer at polling places, work in call centers, and work with local and national organization field offices on Election Day. And AAJ members are encouraged to close their firms on Election Day to allow their employees and colleagues ample time to vote or volunteer.

As Tuesday, Nov. 5 approaches, AAJ will again call on plaintiff attorneys to help safeguard voting rights and make sure that all votes are cast and counted. By volunteering on Election Day, you can help ensure that voters have fair and equal access to cast their ballots. AAJ members should watch their email for more information about ways to get involved or go to justice.org/VPAC.