Picking a Lawyer (Connecticut Edition)


A good friend called the other day. I was unable to take her case due to a conflict. Who would I call if I needed help? she asked.

That is a tough question. The state is awash in lawyers, and a new crop is released on the public every year. Who would I choose?

Of course, the vast majority of individuals charged with crimes have no choice. Courthouse gossip holds that almost 87 percent of those accused of a crime are now represented either by public defenders or by private lawyers working under state contract as special public defenders.

From where I sit, in the trenches, pitching fees to one caller after another in search of counsel, the 2008 recession never ended. If there is a middle class with money socked away for a crisis, it is living in another state. The middle class is dead. Folks are desperate.

I hear certain lines over and over again from callers looking for a lawyer. “I want to be your pro bono case,” they say, knowing full well that lawyers are required to take some work free of charge for the good of the community.

“Thank you for the offer,” I say. “I hear that often. I would like you to be my paying case.”

Another frequent request is for a payment plan. I remind these callers of what I call the first-date rule.

“I’m the ambiguous stranger sitting at the end of the bar at closing time,” I tell them. “You are desperate, and making your best pitch before the bar closes. Come morning, you will forget all about me.” 

I am then assured that my bill will be paid. “I’m not like that,” they say. “You can trust me,” I am told. “I am promising you I will make it good,” I hear.

When I offer to pay my staff in other people’s promises, I am looked at as little more than a fool.

Nowhere in fiction or in the popular literature on lawyers is there anything approaching a realistic discussion of how lawyers are paid. Yet, it is a preoccupation among lawyers. Just last week, I bumped into a young lawyer I admire. He was thinking of quitting. He can’t make ends meet. I tried to talk him in to hanging in there.

But assuming cost were no obstacle, who would I pick for my lawyer if I were charged with a crime?

Picking a lawyer is a lot like getting married. One way or the other, you are bound to your chosen, in sickness or in health, in prison or at liberty. The decision about whom to pick is largely a matter of chemistry, or so I told the caller.

I then proceeded to name three lawyers about as temperamentally distinct as possible. Call them Mssrs. Fire, Nice and Ice.

If I were certain that my case had to proceed to trial, and that my liberty depended on my lawyer’s ability to dismantle the state’s witness, I’d choose Fire.

Who is this lawyer?

New Haven’s Richard P. Silverstein, known to some by the nickname “The Rooster,” no doubt on account of his red hair.

Rick’s zeroing in on 60, and is a daily presence in the criminal courts along Connecticut’s coast. Rick’s scowl is legendary. To see him strut — he doesn’t walk — the streets of New Haven is to wonder who broke his heart, and why he wears his heartbreak on his sleeve.

He tries case after case, bearing the strain of it all with something less than grace. He is Atlas, afraid to shrug lest he drop the world. I like to think of him as a warrior’s lawyer. He’d be my pick in a fistfight any day of the week.

But lawyering is more than brawling. Sometimes, you really can win more with honey than with vinegar. Who would I call if I wanted to arrange the best deal I could get? Why, I’d call Nice.

Yes, I’d call Willie Dow, if I could afford him. Willie’s a senior ambassador of the bar, with a light touch, a sense of humor and a flinty sense of the law’s, and common sense’s, limits and possibilities.

I watch Willie from afar with a sense of wonder. Was he born that smooth? Does his self-effacing charm come naturally? Can anyone really be that nice?

Call me silly about Willie.

But who would I choose if I weren’t sure about whether I wanted trial or a plea, if my case were complex, and required dogged commitment to detail, prudent counsel, and a good friend?

I’d call Ice, the lawyer with nerves of steel.

I am referring to Stamford’s Matthew Maddox, a little known player outside Connecticut’s Gold Coast.

Maddox and I have had clients in common. He’s always mastered the details of the case and spotted issues that cause difficulty if not planned for in advance. In court, he is quiet, steady, even lethal, a cerebral presence capable of the necessary crushing blow. Not once have I seen him lose his cool, no matter how dire the situation.

I just made three friends and created scores of critics. Lawyers, many of them good lawyers, who are not on my short list will feel slighted. I once wrote a piece praising several New Haven public defenders and received many a complaint from other public defenders. What am I, chopped liver? they seemed to chant in unison.

So be it.

Play the field, I say, when trouble comes calling. Muster your resources, be an eager suitor. Then follow your heart. In the valley of the shadow of death we call the courts, it is your best guide.

Also listed under: Journal Register Columns

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