The Other Side of the Courtroom
When you’re facing criminal charges, the stakes couldn’t be higher. Your freedom, your reputation, and your future hang in the balance. Yet most people have never hired a criminal defense attorney before and don’t know what to look for.
After spending 25 years as a deputy district attorney, the last several as Chief Deputy District Attorney for Washington County, I saw hundreds of defense attorneys in action. I prosecuted some of Oregon’s most serious criminal cases, from murder trials to complex sexual assault cases to cases that led to new state legislation. That experience gave me a unique perspective: I know exactly what separates an effective defense attorney from one who’s simply going through the motions.
When I opened McKey Law in 2024 to focus on criminal defense and personal injury cases, I brought that prosecutorial insight with me. Here’s what you should actually look for when your freedom is on the line.
Trial Experience Matters More Than You Think
Most criminal cases never go to trial. They’re resolved through plea agreements. But the attorney you hire needs to be someone the prosecution takes seriously, someone they know will go to trial if necessary. That threat changes everything about how your case is handled.
During my years prosecuting cases, I could immediately tell which defense attorneys had real trial experience and which ones didn’t. The difference showed in how they prepared, how they questioned witnesses, and how they negotiated. An attorney who has actually tried cases, especially serious felony cases, understands what evidence holds up under scrutiny and what falls apart. They know how juries think. They know when to push for trial and when a negotiated resolution serves their client better.
Ask any attorney you’re considering how many jury trials they’ve handled in the past five years. Ask about the types of cases. If the answer is vague or the number is low, keep looking.
Understanding Both Sides of the System
Having worked inside the prosecution system, I understand how cases are built from the ground up. I know how investigators gather evidence, how prosecutors decide what charges to file, and where the weaknesses typically hide. I’ve been part of major crimes investigations and know the pressure points in the system.
This insider knowledge matters. When I review a client’s case now, I’m looking at it through the lens of someone who spent decades on the other side. I know what the prosecutor is thinking, what their priorities are, and what arguments will actually move the needle. I can anticipate their strategy because I used the same playbook for 25 years.
You want an attorney who understands the full picture, not just one side of the courtroom.
Look for Someone Who Handles Serious Cases
Not all criminal cases are created equal, and not all criminal defense attorneys handle the same level of work. Some focus on misdemeanors and lower-level felonies. Others have experience with the most serious charges: murder, attempted murder, major assault cases, complex sex crimes.
The attorney who can handle a murder trial can certainly handle your DUII or theft case. The reverse isn’t always true. During my prosecution career, I handled cases that resulted in life sentences, cases that made statewide news, and cases that led to legislative changes in Oregon law. That level of work requires a different skill set: managing complex evidence, working with expert witnesses, and performing under intense pressure.
When you’re evaluating attorneys, find out what their most serious cases have been. The complexity of their past work tells you something about their capability.
Reputation in the Legal Community
Prosecutors talk. Judges notice. Court staff pay attention. Over 25 years, you develop a reputation, and that reputation follows you.
The attorneys I respected as a prosecutor were the ones who were prepared, professional, and ethical. They didn’t play games or waste the court’s time. They advocated fiercely for their clients but did so within the bounds of the law and professional conduct. When they raised an issue, I knew it was legitimate. When they said their client wouldn’t accept an offer, I believed them.
That kind of reputation matters because it affects how your case is treated. Judges are more likely to take seriously a motion filed by an attorney they respect. Prosecutors are more willing to have honest conversations about case weaknesses with someone they trust.
Ask potential attorneys for references from other lawyers or look at their professional recognitions. Check if they’re active in legal organizations or have received awards from law enforcement or legal groups. During my time as a prosecutor, I received the Oregon Construction Industry Crime Prevention Law Enforcement Partner Award and the Recording Industry Association of America Gold Record Law Enforcement Award. These weren’t just plaques on a wall; they reflected relationships and credibility built over years.
Someone Who Will Actually Fight for You
Here’s something most people don’t realize: a lot of criminal defense is about leverage. Your attorney needs to be someone the other side knows will take the fight all the way if that’s what it takes. I’ve seen too many cases where a defendant hired an attorney who immediately started talking about pleading guilty before even investigating the case.
The best defense attorneys I faced as a prosecutor made me work for everything. They filed motions to suppress evidence. They challenged witness credibility. They brought in expert witnesses. They investigated alternative theories. Even if their client eventually took a plea, the prosecutor knew they’d been in a fight, and that often resulted in a better outcome.
You want an attorney who sees going to trial not as a last resort, but as a real option they’re fully prepared to execute.
The Bottom line
Choosing a criminal defense attorney is one of the most important decisions you’ll ever make. Don’t base it on the biggest ad or the first name that comes up in a search. Look for someone with real trial experience, someone who understands both sides of the system, someone with a reputation for professionalism and results.
Having spent a quarter century inside the prosecution system before moving into defense work, I know what it takes to win. I know what prosecutors fear in an opponent and what judges respect in an advocate. Most importantly, I know that every client deserves an attorney who will fight for them with everything they’ve got.
Your freedom is worth that level of commitment.