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Jessica O’Brien is senior counsel in Tressler’s Insurance Services Practice Group in Orange County, CA. She concentrates her practice on coverage matters, including bad faith and extra contractual liability litigation involving a variety of tort issues. She has a particular interest in trucking and motor carrier, construction defect and sex and human trafficking exposures. Jessica evaluates and analyzes insurance coverage matters, conducts risk assessments for insurance carriers and prepares coverage opinions and position letters. She also manages coverage litigation. Jessica has consistently obtained favorable results for her clients by settling a range of insurance coverage and liability disputes.

Jessica earned her J.D. from New England Law, Boston and her B.A. in International and Comparative Politics from Western Michigan University. 

Where are you from?
I was born and raised in Kalamazoo, Michigan. The city is best known as the hometown of Derek Jeter, for its feature in the movie "Tommy Boy" and for the Kalamazoo Promise. This program provides free college tuition to all students in Kalamazoo who maintain a GPA of 2.0 or higher, allowing them to attend any public or private university in the state of Michigan.

What was your first job?
From ages 13-15, I worked at a winter amusement park called Echo Valley, slinging candy bars and hot chocolate at ice skaters and sledders galore! 

My first legal job was as an intern with Greater Boston Legal Services, where I assisted women facing homelessness due to domestic violence. This experience had a profound impact on my perspective and shaped the kind of person I wanted to be in all areas of my life.

What is on your bucket list?
My bucket list item is to take a long trip to Thailand and work with elephants there. My husband teases me that if I ever disappear, he will find me somewhere in Asia as an elephant trainer.

Why did you decide to become an attorney?
My uncle was an attorney in the Illinois Attorney General’s office for a significant part of his career. He had a big impact on my childhood, and I wanted to one day be as smart as he was. As I got older it became a natural career choice given my love for reading and an inherent pull toward discussion and advocacy.

What is your favorite travel spot?
My brother was stationed in Italy for a long time, which gave me the opportunity to visit the country five times. My husband and I also spent our honeymoon there. There is so much to see and enjoy! Instead of taking numerous scenic photos, my husband captured a picture of me enjoying every meal at the restaurants.

Why did you choose your areas of practice?
Many people view insurance as a mundane necessity and often feel frustrated about having to pay for it. However, as an attorney, I encounter insurance claims that involve fatalities, life-altering injuries and disasters—situations that many individuals find frightening. By thoroughly analyzing these circumstances, I can make a meaningful impact during some of the most challenging times in their lives. This work gives me a sense of purpose.

What do you like most about Tressler?
Tressler is a group of some of the most intelligent and good-natured humans I have had the pleasure of getting to work with. Beyond work, everyone has such an array of cool hobbies and interests, from pilots to marathon runners to emo music aficionados!

What are you most proud of, professionally and/or personally?
I coach a youth soccer team for children aged 5 and 6 in our local parks and recreation program. The kids come from various backgrounds, and initially, I became a coach as a way to give back to the community. Over time, I’ve realized that these kids give me much more than I could ever give them. Their kindness and innocence at this age, along with their big emotions, are truly inspiring.

Throughout the season, they make significant progress. They begin as a bumbling and confused team, sometimes even scoring in the wrong goal and shedding many tears. By the end of the season, however, they are confidently dribbling the ball, scoring goals and having a better understanding (kind of!) of their positions on the field. The transformation is remarkable.

Jessica O'Brien can be reached at jobrien@tresslerllp.com. Learn more about our attorneys by visiting www.tresslerllp.com/attorneys.