The View from the Other Side of the Table
For a quarter century, I sat on the prosecution side. I handled some of Oregon’s most serious criminal cases as a deputy district attorney, eventually serving as Chief Deputy District Attorney for Washington County. I watched hundreds of defense attorneys work. Some were exceptional. Many were not.
Now that I’ve moved into private practice at McKey Law, people often ask me what makes the difference. What should someone facing criminal charges actually look for in a defense attorney? The answer isn’t what most people expect.
Trial Experience Matters More Than You Think
The biggest gap I saw from the prosecutor’s table was between attorneys who had real courtroom experience and those who didn’t. Many defense lawyers rarely go to trial. They negotiate plea deals, handle paperwork, and hope the case resolves without a jury.
But here’s the problem: prosecutors know who will actually fight. When your attorney has a track record of taking cases to trial and winning, it changes every conversation. Plea offers improve. Evidence gets scrutinized more carefully. The entire case is treated differently.
I spent years as a member of Washington County’s Major Crimes Team, prosecuting murder cases, sexual assaults, and attempted murder. I know what it takes to prepare a case for trial. I also know how prosecutors evaluate defense attorneys. If they sense hesitation or lack of experience, they push harder.
Understanding Both Sides of the System
Most defense attorneys have only ever worked defense. They learned the criminal justice system from one angle. That’s a disadvantage.
Having prosecuted cases for 25 years before moving to defense work, I understand how prosecutors build their cases, what evidence they prioritize, and where their weak points typically hide. I know the difference between a strong case and one that looks strong on paper but won’t hold up under cross-examination.
This perspective shapes everything. When I review discovery in a criminal case now, I’m not just looking at what the state has. I’m thinking about what I would have done as a prosecutor, and more importantly, what I would have worried about.
The Importance of Relationships and Reputation
Criminal defense isn’t practiced in a vacuum. Your attorney will interact with judges, prosecutors, court staff, and law enforcement. Relationships matter.
I worked alongside the same prosecutors, judges, and officers for decades. I know how the system works in Washington County. I understand local court culture, individual judge tendencies, and how different prosecutors approach different types of cases.
That familiarity doesn’t mean cases get special treatment. It means your attorney can navigate the system efficiently, knows who to talk to and when, and has credibility built on years of professional relationships. When I say something about a case, people listen because they know my track record.
Look for Someone Who Has Handled Your Type of Case
Not all criminal cases are the same. A DUI requires different expertise than a murder charge. A sex crime defense demands specific knowledge that doesn’t overlap much with theft or assault cases.
I prosecuted murders, sexual assaults, hit-and-runs, and violent crimes. I know these cases inside and out. If you’re facing serious felony charges, you want someone who has been in that arena before, not someone who mainly handles misdemeanors and is hoping to figure it out as they go.
Ask specific questions. How many cases like yours has the attorney handled? What were the outcomes? Have they taken similar cases to trial, or do they always settle?
The Reality of High-Profile Cases
Some attorneys advertise their work on high-profile cases as a selling point. What matters more is the outcome.
I handled many of Oregon’s most serious and high-profile cases during my time as a prosecutor. I learned that media attention doesn’t determine case difficulty. Some of the hardest-fought cases never made the news. What matters is the legal complexity, the evidence, and the skill required to navigate it.
When evaluating an attorney, look past the headlines. Focus on the substance: Did they win? How did they win? What was their strategy?
Questions to Ask Before You Hire
If you’re facing criminal charges, here’s what I’d ask any potential defense attorney:
How many jury trials have you handled in the past five years? What were the verdicts?
Have you prosecuted cases before, or have you only worked defense?
How many cases like mine have you handled, and what were the results?
Do you have established working relationships with the local court system where my case will be heard?
Will you be the one handling my case, or will it be passed to a junior attorney?
These questions cut through marketing and get to what actually matters: experience, skill, and results.
Trust Your Instincts, But Verify with Facts
Finally, trust matters. You need to feel confident in your attorney. But don’t let personality replace competence.
I’ve seen clients choose attorneys because they liked them personally, only to regret it when the attorney couldn’t deliver in court. On the other hand, I’ve seen clients work with attorneys who weren’t particularly warm but who fought brilliantly and won cases that seemed unwinnable.
Look for both. Find someone you trust and who has the proven experience to back it up. Your freedom, your record, and your future depend on it.