Jonathan Bailey ’12

Jonathan Bailey
December 7, 2023

Jonathan Bailey ’12 grew up in Monroe, New Hampshire, and recalls, “It was a great place to grow up because there was enough space to explore the woods and mountains, but it was close enough to the Academy that I could easily meet my friends.” His sister, Caroline graduated in 2016.


He said, in addition to being involved with student government and the lacrosse team, his “favorite class, as difficult as it could be, was string ensemble with Jason Bergman (former Performing Arts Faculty), where I studied violin and viola. Thanks to him, I have a base knowledge of music theory and have transposed those skills to learn the guitar, piano, and bass guitar after graduation. “Adam Kennedy ’92 (former Technical Education Faculty) and Richard “Dick” McCarthy (former English Faculty) had the biggest impact on me. They really helped me see that most of the barriers we believe are in our way are mental. Also, the lessons I learned on the sports field have guided me through college, graduate school, and my career.”


After graduating from SJA, Jon attended the University of New Hampshire and then Hofstra University School of Law. He said, “I think the Academy experience prepared me to effectively juggle the multiple responsibilities that college throws at you.”


“I never expected to be practicing law. I had been training Mixed Martial Arts for a little over two years while in college. I was preparing for my first fight and didn’t have any classically professional aspirations (sorry Mom, I don’t think I told you that). However, I’d sustained some injuries that would have made a career of fighting difficult. While injured, I had a college professor, a week from graduation, tell me I should think about law school. So, I did.”


Now, Jon is the Assistant District Attorney at the Harris County, Texas, District Attorney’s Office, where he is the Chief Prosecutor in the County Criminal Court of Law No. 14. The best thing about his job? “There is never a boring day; something unexpected will always happen, and you have to be able to adapt to rapidly changing circumstances in the courtroom. However, by the same virtue of the job’s unpredictability, it’s very easy to burn out.”


Jon recently came from the Vehicular Crimes Division as a special prosecutor, and many of the responsibilities he had in that division have carried over to his recent placement. VCD prosecutes crimes related to motor vehicles and intoxication, such as DWI, Intoxication Assault, Intoxication Manslaughter, and Murder. These cases are very technical and require the prosecutors in this division to work closely with law enforcement. He elaborated, “For example, during a one-week assignment, we are on call to respond to Vehicle Fatalities where intoxication is suspected. We travel to the crash scene and assist the officers with their legal questions, draft their warrants on scene, and sometimes direct their attention to important details. In addition to the “call-out” responsibilities, I oversee three other attorneys in one of the County Courts. I help them prepare for jury trials, teach them how to properly build the State’s case, and step in to get them back on track if things go off the rails in court. Lastly, I also prepare and try my own felony cases. This involves jury selection, directing and crossing witnesses, and researching case law in anticipation of what the Defense will argue. So, there really is no normal day. Sometimes, I’m at the office for 8 hours; other days, it can be 24.”


What’s one piece of advice Jonathan has for current SJA students? “No matter what you do, explore other interests outside of your field of work or study. The more experience and knowledge you can draw from, the better you will be at whatever you choose to do for work. It will also help you avoid getting burned out.”


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