Opening Moves – A Childhood with Chess
For some kids, childhood was about toy cars and soccer games. For Adam Fleming, it was chess. From an early age, he showed a rare talent for the game.
He learned the game from his father, playing casually with him for some time. When high school rolled around, Fleming started taking chess seriously, playing more competitively. He started reading books, studying strategies, and entering local tournaments.
“My dad and I went from casual games to real, competitive matches,” Fleming recalls. “Eventually, we were evenly matched. It was great to have a reliable sparring partner.”
Middle Game Transitions – Coming Back to The Board
Adam stepped away from chess during college, law school, and the early stages of his legal career. But, about 10 years ago, he found his way back to the game he had loved since childhood.
Since then, he has been steadily returning to top-notch form, playing a slew of online opponents, reading up on chess strategy, and refining approaches to potential scenarios faced in the heat of real-world competition. The hard work has paid off. His recent first-place finish in his class at the 2025 Arpad Elo Open marked a major milestone in his competitive journey.
“In any event like that, you’re playing well-prepared, experienced competitors,” he explains. “Nobody’s playing casually and small mistakes can cost you the game.”
Calculated Lines: Training Meets Opportunity
His preparation came full circle during the event.
“Some of the situations that came up were things I had trained on,” he said. “When you see your study translate into success over the board, it builds confidence and helps you focus on what really matters. When your preparation pays off, it’s incredibly validating.”
Next up for Fleming is the U.S. Open in Madison, Wisconsin, a much larger and more competitive tournament. He sees the Elo Open as a warmup, helping him prepare for the next level of talent he will face.
“If I get more than half the available points in Madison, I’ll consider it a win,” he says with a half-smile. “The field is that strong.”
Time Trouble: Balancing Law and the Love of the Game
So, how does a full-time attorney find time to compete at this level?
For Fleming, it comes down to efficiency and making the most of small windows of opportunity. Time is always the biggest constraint.
But online platforms, training tools, and YouTube resources make it easier to study and stay sharp.
Tactical Thinking: Parallels Between Law and Chess
He also sees clear parallels between chess and the legal world, development in one yielding dividends for both. Chess and the practice of law share the requirement of solving complex problems under tight deadlines. In each, overthinking and wasting time can mean losing the advantage.
Experience and good judgment, he said, are essential in both fields.
“Clients expect cost-effective solutions and that means using time effectively. You have to decide quickly what’s necessary to dive deep into and what’s not. That same skill applies when you’re evaluating positions over the board.”
Endgame Strategy: Staying a Few Moves Ahead
While not everyone at the firm knows about his competitive side, Fleming says a few colleagues are aware of the chess board that sits in his office, though few have taken him up on a game. For now, he is focused on sharpening his skills both as an attorney and a player and is always thinking a few moves ahead.
“In my practice area, I am drafting estate planning documents that most of my clients hope will not have to be used for many years. Just like understanding of the endgame is widely regarded as the pathway to greater success in chess, my work in Estates and Trusts requires me to always keep the long view in mind,” said Fleming. “Although it can be very easy to get caught up in the complex details of solving our clients’ immediate problems, it is critical for us as lawyers to understand the long-term effects of the short-term steps we advise our clients to take.”
Adam Fleming is a partner with WilliamsMcCarthy LLP. He is a part of the Estate Planning group, advising clients in the areas of estates and trusts. He can be reached at afleming@wilmac.com or (815) 987-8934.
