✏️ Legal Pad
The Worst Case I Ever Tried
When I was an assistant solicitor, I prosecuted a pro se defendant charged with possession of cocaine, third offense- a ten-year felony. On paper, it should have been a routine case, but when defendants decide to represent themselves, things can go sideways quickly.
She approached a DUI checkpoint and did the one thing you absolutely should not do (setting aside the obvious): she cut a U-turn directly in front of the troopers. They stopped her immediately and, instead of staying put, she jumped into the back seat of the car, a move that instantly raised officer-safety concerns and is liable to get someone shot. Troopers broke the rear window with a baton, and what followed was some of the most surreal body-cam footage I’ve ever seen: the defendant shoveling packets of cocaine into her mouth by the handful.
At that point, the officers weren’t thinking about making an arrest, they were thinking about keeping her alive. She was rushed to the hospital, her stomach was pumped, and the baggies tested positive for cocaine. It was a slam-dunk case, and has to be the purest example of “possession” I’ve ever seen.
She was a Navy vet suffering from drug fueled mental health issues, and I felt bad for her- I have deep respect for anyone who served. But she refused every plea offer, insisted on going to trial, and fired two different public defenders. So there she was, representing herself. There’s an adage about how a lawyer who represents himself has a fool for a client, and this aligns with that.
Trying a case against a pro se defendant is the most uncomfortable position a prosecutor can be in. If you win, it feels like you beat up on a toddler. If you lose, you start wondering whether you should find a new line of work. There is no middle ground. And no matter how strong the evidence is, the risk feels existential.
To this day, I’ve never been more nervous waiting for a verdict. When the jury brought back a "guilty," the relief hit harder than it should have, almost embarrassingly so. That's what pro se cases do to you. What followed was worse: pity. She could have (and should have) pled to a lesser charge. She could have avoided a devastating sentence. Instead, she chose a path that led straight to a prison term she's still serving. Play dumb games, win dumb prizes.
She may have been the one convicted that day, but years later, I'm obviously still the one thinking about that case. Some trials haunt you not because of how hard they were to win, but because of what would happen if you lost.
💡 Sidebar
A couple of weeks ago, our extended family went to see White Christmas at the Greenville Theatre. It’s a smaller venue, with a smaller budget, and none of the spectacle that comes with the Broadway tours at the Peace Center. And yet, sitting there watching, it struck me that the talent on that stage, much of it local, was every bit as good as what we’ve seen roll through town on national tours. In some moments, it was better.
Those performers knew the room. They knew the audience. The performances weren’t calibrated for a generic crowd in a different city; they were tuned to the people sitting just a few rows away. It felt personal and confident in a way that big productions sometimes aren’t.
The same dynamic exists in the courtroom. There’s a perception that bigger firms and bigger cities automatically mean better lawyering. Sometimes they do. Often, they don’t. Trial work is local work. It’s knowing the venue, understanding how jurors here listen, and speaking plainly to people who are your neighbors.
The best advocates aren’t always the loudest or the most decorated. They’re the ones who understand the room they’re in and connect with the people who decide the case. Just like that stage at the Greenville Theatre, excellence doesn’t require a national tour, it requires preparation, authenticity, and tapping into the community.
⚖️ Closing Arguments
A few weeks ago, I tried a case that never should have been complicated. A tractor-trailer made a right-hand turn from the far-left lane: a classic wide-turn situation that any properly trained CDL driver knows not to make. The result was predictable and preventable. My client was hit and suffered a severe foot fracture that changed how she walked, worked, and lived her daily life. She's 23 and will deal with it for the rest of her life.
From day one, the defense didn’t take the case (or us) seriously. We litigated it for a year and a half- depositions, experts, motion practice, trial preparation- and the highest offer the insurance company ever put on the table was $50,000. Roughly half of her medical bills. That number didn’t reflect the injury, the responsibility, or the risk. It reflected a calculated belief that the case would never be tried.
That belief changed quickly. After the first day of trial, the offer jumped to $300,000. We said no. And as we were preparing to start the second day, opposing counsel handed me a handwritten note across the table. It said simply: “We have one million.”
Showing that note to my client was one of the more satisfying things I’ve gotten to do in a courtroom.
That kind of result doesn’t come from emails or mediation statements. It comes from the arena. From standing up in front of a jury, presenting evidence, and letting ordinary people decide what accountability looks like. It comes from a system that still believes disputes should be resolved in open court, not quietly discounted behind closed doors by algorithms.
That’s why trial work matters. And that’s why, for all its imperfections, we have the single best civil justice system ever constructed- one that empowers citizens, demands preparation, and forces responsibility when it’s earned. Those 12 strangers in the box changed my client's life in ways they'll likely never know. And ours is the only country in history where things like that happen every day, which is both astounding and humbling.
Court is in recess- see you next Friday. Merry Christmas.
