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    Wisconsin Lawyer
    October 07, 2020

    10 Questions: Aileen Henry: Fighting for the Underdog

    Kenosha lawyer and U.S. Army veteran Aileen Henry runs a small criminal defense law firm in Kenosha. Born in Jamaica, she learned from her grandparents the value of hard work and giving back to the community – values she carries into her law practice.
    Aileen Henry

    What was it like growing up in Jamaica?

    I was raised in York Castle, which is a rural, mountainous community in the northern parish of St. Ann, Jamaica. I was raised by my paternal grandparents, who considered me their 13th child. I often look back in amazement and wonder why two people over the age of 70, who had already raised 12 children, would agree to take on the task of raising a toddler still in diapers. But I’m thankful that they did. They showered me with love and provided me with an amazing childhood.

    My grandparents sacrificed a lot when they decided to raise me. Both left school at age 13 to work on their families’ respective farms. Despite their limited educations, my grandparents were very active leaders in their community and their church. They wanted a different life for me and their children – a better life – so they instilled in all of us the value of hard work, education, and the need to give back to the community. They died before I became an adult, but I hope that I have made them proud.

    What brought you to the United States?

    When I was about 3 years old, my aunt, a U.S. citizen, petitioned for my father and me to emigrate to the United States. The process lasted 16 years, and I moved to Florida in 1996 with my father. I moved to the United States because there was a lack of educational and employment opportunities in Jamaica at the time.

    What led you to serving in the U.S. Army?

    I had been living in the United States for about four months when one night I saw an ad for the United States Army on TV. The gist of the ad was that the Army was offering a sign-on bonus of $30,000 for college. The very next day, I took a bus to the recruiter’s office and signed up. Turns out that I did not qualify for the sign-on bonus. Nevertheless, enlisting in the Army was one of the best decisions I have made in my life.

    My first tour of duty was in South Korea. I loved every minute of my time in Korea. I finished my enlistment at Fort Bragg, N.C. The Army provided me with an opportunity to travel. I made lifelong friends in the Army. I am very proud of my service in the Army. I view my service as my way of giving back to my adopted homeland, which has embraced me and provided me with so many opportunities.

    How did you end up in Wisconsin?

    I met my husband in 2000 while I was still enlisted in the Army. We actually met online. Online dating was not as common back then as it is now, so my husband and I told our friends and family that we actually met at the airport – which is true, because that is where we physically met for the first time. Most people didn’t realize we first met online until we revealed it at our wedding in 2008. In any event, my husband is originally from Milwaukee, so after my enlistment ended, I moved to Wisconsin to be with him.

    What made you decide to pursue law?

    My grandparents were highly active in our community. They were known in the community as always being willing to help anyone who was in need. Their door was always open to anyone who needed a meal or a place to stay. They were always willing to share the little that they had. I loved watching them taking care of the members of our community. Whenever there was a need in the community they tried to fill that need. It is their sense of justice that led me to pursue a career in law, and the values they instilled in me are values that I carry with me today in my law practice.

    After graduating from law school, I worked for a big law firm in Milwaukee in its conflicts department. I was miserable. I hated being tied to a desk all day. I wanted to go to court, try cases, interact with clients. A friend suggested that I take pro bono public defender cases in Kenosha County, which at the time had a shortage of lawyers taking public defender cases. My first case was a disorderly conduct matter. I remember being so nervous, but the local attorneys were quite welcoming and very giving of their time to me. I then quit my job and started out taking overflow cases from the Kenosha Public Defender’s Office.

    What attracted you to Kenosha?

    Kenosha is such a beautiful little town with a big-city attitude. Its lakefront is stunning. The people are amazing. But most important, I love being a member of the Kenosha bar. I have found my bar colleagues to be extremely supportive.

    What do the recent events in Kenosha and elsewhere mean to you?

    We’ve seen extensive coverage of violence against demonstrators in Portland and Minneapolis. We’ve seen marches around the country, shootings from around the country. But the shooting of Jacob Blake brought things home to Kenosha. It made them local and took them from the “big” cities to an in-between town – fourth largest in the state, but small compared to Chicago or Milwaukee – with a distinctive name somewhere in Wisconsin. The shooting of Jacob Blake took things to main street. The heartland. To a quaint downtown. To streets people recognize because they’ve walked them or walked others like them.

    The Kenosha unrest, once again, brought together a diverse group of protestors. But we really got to see the Midwest. We saw Orthodox Jews and Christians praying together. Black and white. Attorneys and blue-collar workers. Kids and adults. Artists and advocates. It was a beautiful bright light amid so much darkness.

    I also was struck by the way law enforcement officers interacted with unarmed Black protestors versus highly armed white “militia.” Questions still remain about whether officers formally coordinated with armed civilians. But their passive allowance to let such individuals roam the streets and their active appreciation of them (water bottles, actually thanking them) show the massive disparity between how people are perceived as threats. Without words, their behavior said Black is dangerous and white is all right, no matter who has the weapon.

    What is the biggest impact COVID-19 has had on your ability to serve your clients?

    COVID-19 has significantly changed the way in which I communicate with my clients. Since COVID-19, all my communications with my clients have been via phone, Google Hangouts, or Zoom. I miss having face-to-face interactions with my clients.

    What do you love best about your legal work?

    I love being a criminal defense attorney. I love fighting for the underdog. I know what it means to be the underdog. My clients are underdogs when compared to the might of the state of Wisconsin as plaintiff. I love the sense of accomplishment I get whenever I fight for a client. People usually ask, “why do you enjoy representing people accused of committing these horrible crimes?” Well, most of my clients are good people who have made a mistake. And, I don’t believe that a client’s mistake defines who they are. I represent people, not crimes.

    Tell us about your proudest moment as an attorney.

    I’m most proud of the relationships that I have developed with some of my clients. These clients and their families have embraced me as a member of their families. I treasure their friendships. I am proud that despite the nature of our initial meetings, we were able to navigate the criminal justice system together and come out on the other side as lifelong friends.

    What is your relationship with golf?

    I have been golfing for about 15 years, and I’ve developed a very deep love-hate relationship with golf. There are many days when I have wanted to quit and have fought to keep myself from crying on the course. But then one good golf shot is enough for me to fall right back in love with the sport. This may sound stressful, but golf has actually played a large role in helping me to cope with my anxiety disorder. To have a good round, I must be patient, control my emotions, and think critically. So, while I golf to escape the realities associated with my stressful job, I carry the skills I learn on the golf course with me into my practice as well as my marriage and friendships.

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