Criminally Yours: Don't Plead Guilty

Don't take that first plea, especially on a misdemeanor. The stigma it carries will get you rejected from jobs, loans, licensing, and even housing.

When I was a young public defender working for the Legal Aid Society in New York City, we were posted in arraignments three times a month, handling dozens of new cases, mostly misdemeanors, at each appearance.

We learned fast how things worked. Some judges were tougher than others, setting high bails for the most incidental of offenses. Others – very few – realized, even back then, how criminalizing drug possession and putting people in jail for their addictions was not a great use of public monies and did nothing to help keep them from coming back.

Most deadening was dealing with the clients too poor to make bail. This was the vast majority. For them, even if they didn’t commit the crime, it made sense for them to say they did. Simply put, they would get out of jail quicker if they just pleaded guilty than if they fought their case. It took so long to get to trial that they inevitably spent less time in jail by pleading guilty. With so many vagaries – unavailable judges, courtrooms, jurors, attorneys, cops, etc. — it was clear that the benefit of going to trial and being found not guilty was just not worth the cost of being jailed at Rikers. The minimum turnaround for a low-level misdemeanor to get to trial was generally six months. Most cases went longer. The maximum time a defendant can be sentenced on misdemeanor is one year, counted as eight months with good time, so it never really made sense NOT to plead guilty once you were stuck unable to afford bail.

One of the most frustrating realities as a young attorney was the feeling of being a cog in the wheel of injustice. It was my job to explain to a not-guilty client how pleading guilty was his quickest get-out-of-jail ticket. Then I’d have to advise him how to plead guilty to the crime he never committed — in open court, under oath. I justified this to myself in a number of ways: 1) I was young, 2) I had no power, 3) maybe he did commit the crime, I wasn’t there, after all, and 4) I couldn’t blame him for wanting to get of jail.

This system sets up a vicious cycle developing criminal histories for mostly young black and Hispanic males that bring so many negative consequences that no one, especially not the defendant eager to get out of jail, can either appreciate or foresee at the time they grab their first plea. Once you’ve got one conviction, even for a violation, you’re looked at differently in criminal court. On your next arrest, the presumption of innocence starts to morph into the presumption of guilt.

If, God forbid, on that first case, you fail to do even one day of community service, you’re branded a “risk” to return to court, a warrant is issued, and bail for any subsequent crime will be high.

The system is unforgiving, the consequences brutal.

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I’d like to tell every young person just starting on his or her journey through life, don’t take that first plea, especially on a misdemeanor. The stigma it carries will get you rejected from jobs, loans, licensing, and even housing.

All because you couldn’t make bail. What a senseless shame.

The excellent cover article in this week’s New York Times Sunday magazine, “The Bail Trap,” explains the ins and outs of why exactly this happens, who benefits, and how difficult this structure we’ve accepted for decades will be to change.

And it is changing, however slowly. Pushed by articles like this, the issue of race bias is back in the forefront. Many tough-on-crime conservatives are beginning to recognize that too much money is going into the criminal justice system for too little results. Bail reform is on the horizon.

To be honest, I haven’t seen much change in my day-to-day work in the criminal-court trenches. Judges are still putting poor people in jail for what a wealthier person would consider a pittance.

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A lot more has to happen, but at least the discussion has started.


Toni Messina has been practicing criminal defense law since 1990, although during law school she spent one summer as an intern in a large Boston law firm and realized quickly it wasn’t for her. Prior to attending law school, she worked as a journalist from Rome, Italy, reporting stories of international interest for CBS News and NPR. She keeps sane by balancing her law practice with a family of three children, playing in a BossaNova band and dancing flamenco. She can be reached at tonimessinalw@gmail.com or tonimessinalaw.com.