By Eleanor H. Sills
A real-life Captain America. Judge Robert “Bobby” E. Long, Jr., is the quintessential North Florida judge. A many-generation Floridian, Judge Long grew up in North Florida, attended Florida State High School when it was located on Florida State University’s campus, and received a Bachelor of Science in Finance from Florida State University and a law degree from the University of Florida. He currently serves as a Commander in the United States Navy Reserves. He is the first lawyer in his family, a veteran, a member of a band, a surfer, a father of four boys, and a husband. Put simply, Judge Long is a “Florida man,” but in the best way possible.
Judge Long understood the concept of law from a young age. As a self-described “typical knucklehead—likely worse—”middle-schooler, he joined the local Sheriff’s Explorers Group, which he discovered through Boy Scouts. Little did he know that his involvement with the Sheriff’s Explorers Group would start his pathway to the bench. He remained involved with the group throughout middle and high school. The group sparked his interest in law enforcement and ultimately helped him receive a scholarship to attend the police academy at nineteen.
He was admitted to the Florida Bar in 2008 and began his legal career as a Judge Advocate in the United States Navy. Afterward, he worked at Rumberger, Kirk & Caldwell, P.A., in Tallahassee from 2013–14, practicing in the civil litigation field. Eventually, he landed his dream job of being general counsel for the Leon County Sheriff’s Office. He worked for the Sheriff’s Office from 2014 until his appointment on June 26, 2016, to the Second Judicial Circuit Court by Governor Rick Scott. He was then appointed to the First District Court of Appeal on June 10, 2020, by Governor Ron DeSantis.
Luckily, throughout his life, Judge Long had many wonderful mentors. As a Sheriff’s Explorer, his mentors encouraged him and held him accountable. They taught him the importance of recognizing that some things are bigger than himself. In the Navy, he was surrounded by inspiring people, who showed him how to lead and work in a cooperative environment. As a civil attorney, he had a mentor who was generous with his time and made the effort to teach him not only how to be a lawyer, but about the business of the law and how to make a living in this career.
If it feels like Judge Long has always worn many hats in his life, that’s because it’s true. He was general counsel to the Leon County Sheriff’s Office while serving as a Major on the Executive Command Staff; he is currently a Commander in the United States Navy Reserves and an appellate judge. When asked how he does it all, he recognizes that it is not easy, and his wife often reminds him that he is doing a lot. But Judge Long enjoys challenges and trying different things, and sometimes it is just too hard to say no. He has always held a few jobs throughout his life, so wearing many hats is second nature to him.
His background as a circuit court judge has proved to be a valuable asset while serving on the First District Court of Appeal. All thirteen First District judges have extraordinary backgrounds, and each brings unique experiences to the table. There are two former trial judges on the First District, and Judge Long recognizes that it is always good to have a couple who have been in the trenches; it can be tempting to Monday-morning quarterback and think “I would have objected here,” or “I would have ruled on that issue differently.” But with his trial experience, he better understands the real world and the human experience of having to make decisions on the fly.
When asked about his writing style, he laughed and said he was no expert. He recognizes that writing is an art, not a science. He believes personalities show through in your writing, and it can reflect you and your thoughts. Personally, he tries to be clear and not hide the ball, noting that in his opinions he provides an upfront paragraph that explains where he is going and why he reached the conclusion he did. While he loves to read a fun Justice Scalia opinion, he feels that his work at the First District is the “people’s work” of resolving disputes. So he hopes to write in a way that the average layperson can easily understand his opinions.
His biggest advice to young lawyers and law students hoping to break into the appellate field is to go clerk—which he immediately laughed at and said he did not do. He feels clerking helps young lawyers understand how to approach a case and how a case moves through the courts. In addition, clerking opens doors for young lawyers and allows them to network with those involved in the appellate field.
With four boys, Judge Long’s life is full. In what little time he has left after work and other commitments, he enjoys sailing with his boys, and all of them know how to work the sailboat. Recently, he went sailing around the Florida Keys with the Boy Scouts—he quipped the waves were not quite large enough to go surfing. He still occasionally plays in a band. Although he plays a much smaller role than he did before taking the bench, he revealed that the band previously recorded an album and has played at some of music’s biggest venues.
So how does he balance it all? “A daily balance,” he says with a chuckle. He humbly told me that it is the power of the little things, treating people well, and being kind and engaged that helps him remain balanced. In sum, Judge Long is generous, hard-working, modest, multi-talented with many hidden talents, and a wonderful addition to Florida’s judiciary.
About the Author: Eleanor H. Sills is an appellate attorney with Banker Lopez Gassler P.A. She also assists in the firm’s trial litigation support group. She previously clerked for the Honorable Ricky L. Polston of the Supreme Court of Florida and worked in the appellate division of the Agency for Health Care Administration. She is a member of the Florida Bar’s Appellate Practice Section and a barrister in the First District Appellate American Inn of Court.
