EPISODE · Sep 1, 2026 · 24 MIN
The Case For The "Deep End"
from The Case For... (with Matthew Campobasso) · host matthew.r.campobasso
It's late August 2006. I'm twenty-eight years old, sitting in my office on my first day as an Assistant State's Attorney in McHenry County, Illinois. I've been filling out health insurance forms for ten minutes when the Chief of the Criminal Division walks in, tosses a case file on my desk, and tells me I need to be in Courtroom 301 in fifteen minutes to pick a jury and try a DUI trial. I don't have my law license yet. I tell her I can't try a case alone. She tells me I won't be alone — Bill will be in the courtroom with me. I walk upstairs and find Bill sitting in the back row of an empty courtroom doing his own paperwork. He informs me that the rule only says he has to be in the room. Not at counsel's table. Not helping. In the room. Back here. Good luck. Less than eight hours later, I had picked a jury, tried my first solo trial, and gotten my first guilty verdict. Then I went back to my desk and finished my insurance paperwork. This episode is about the deep end — the place where your readiness runs out and all you have left is yourself. Sometimes you jump. Sometimes someone throws you in. The water doesn't care how you got there. The learning is the same. I examine the difference between being ready and being capable, what Nicole taught me by removing my ability to hesitate, what Bill taught me by sitting in the back row and letting me figure it out, the difference between support and rescue, and why the deep end — whether chosen or forced — is the most important place you'll ever visit. If I had been given a week to prepare for that trial, I would have been more ready. But I would have missed the most important lesson of my career: a week of preparation teaches you how to try one case. Being thrown in teaches you that you're capable of trying any case. The deep end doesn't wait for ready. It waits for you.
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The Case For The "Deep End"
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