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Plead Guilty or Take it to Trial? The Ultimate Dilemma

October 10, 2024
By Josie Mastandrea
Josie Mastandrea, a rising junior at the University of Richmond, spent the summer of 2024 shadowing Attorney Chris Fiorentino to develop a better understanding of what the life of a criminal defense lawyer looks like. The following article is one of a series documenting the insights she derived from the experience. 

I’ve always loved courtroom dramas–the cross-examinations turned on-the-stand confessions, the satisfying closing arguments, the verdict for the underdog. But any lawyer will tell you these movies don’t exactly show you what it's like to practice law in real life. Sure, real trials can be dramatic, but most cases never even get to that point. Surprising, right?


Chris was a prosecutor for a couple years before he went into criminal defense and personal injury law. He told me that as a prosecutor, the goal in every case is to settle – to be so prepared that the other side knows they can’t win at trial, and now just wants to make a deal. When you’re dealing with so many cases at one time, it doesn’t make sense to waste the time and effort that goes into a trial when a simple agreement outside of the courtroom will achieve practically the same result. Now being on the other side of things, he explained that things aren’t quite as simple. As a current defense attorney, he’s the one helping defendants make what is usually the hardest decision of their life so far: whether to take a plea deal or take their chances at trial.

The Game Time Decision 


This past week, I saw just how hard this decision can be. I was in Wrentham District Court with Chris when he got a call–a colleague told him one of his clients was being transported to court that morning for an arraignment. The client had a warrant out for her arrest on a couple of assault and battery charges, one for domestic violence and one with a deadly weapon. He couldn’t make it to Wrentham to handle the hearing–Chris was being called in as the ringer. 


Chris and I went down to the lock up immediately. The lock up is where defendants already in custody are held before and after they appear in court–it's like a mini jail. I asked him whether we were going to look at the client’s case file first, but he told me the most important thing at the moment was that the client felt comfortable, knowing that at least for the short term, her future was in his hands. 


The client we met in the lock up was not at all who I expected to see in for assault charges. She was a young girl, small, pretty, and respectful even amid her distress. The two of them discussed the case, he shook her hand, and we went back up to the courtroom.


The Back and Forth


Chris went to work to figure out what the young girl’s options were. As soon as he looked at her file, which included a record three pages long consisting of drug charges, restraining order violations, and now the assault and battery charges, he told me the prosecutor was going to file a motion to revoke bail. Essentially, the prosecutor is going to argue that this girl is dangerous and needs to await trial away from the public and the victim of her alleged crimes. 


We went to talk to the prosecutor, who told Chris that was exactly what he was going to do. When Chris asked about a plea, he said he would drop the deadly weapon charge, but not the domestic. 

Chris went back down to the lock up to explain to the client that she could either plead guilty to the domestic assault charge, and probably get a year or so of probation, or she could go to trial, where the charges could get dismissed altogether. The issue is this motion wants to revoke bail. If successful, it would mean this young girl spends a minimum of 30 days in jail before the trial if that’s the way she wants to go–not to mention that she could end up with a greater sentence if she’s found guilty at trial. 


Chris recommends that she go to trial, nonetheless. He explains that if she does, her accuser probably won’t show up the day of–case dismissed. Nothing gets added to her record, no probation, 1 month and done. Chris knows that it's easy for him to say and much harder for her to do. When he made this suggestion, she dropped to her knees, sobbing, at the thought of going back to jail, and she had been there just one night.

Only a year of probation might sound more appealing than sitting in jail for a month, but Chris knows that probation would mean a long rehabilitation program, mandatory drug testing that could lead to violations, new charges, then more probation. She might get tied to the court system for the next few years. As crazy as it sounds, a month in jail is the better option here.


After a long conversation, she agrees she should go to trial. We go back up to the courtroom to wait for her case to be called. Then, the court marshal motions to Chris to go back down to the lock up–she’s changed her mind. We go down, she tells him she can’t go back to jail, Chris tells her he understands and respects her decision, and we go back up to the courtroom. This sequence takes place about three more times–trial, no trial, trial, no trial. 


How Do You Make the Choice?


Usually, your attorney will be able to see that one bad option is better than the other. 


The Benefits of a Plea Deal



Plea deals provide a defendant more certainty because a tougher sentence could be issued at trial than is offered in a plea. 


The Benefits of a Trial


A trial, on the other hand, is the only way to get justice if you’ve been wrongly accused. Moreover – even if the defendant committed the crime just as the prosecution says – that doesn’t mean the prosecutor will have all the evidence it needs to prove the charges on the day of trial.


The Non-Answer to an Impossible Question


The question truly has no answer. That’s why, at the end of the day, it's entirely the client’s decision. An attorney can assist in explaining a client’s options and managing strategic legal decisions, but in the end, their job is to carry out the client’s wishes, not their own. 


This is also why the 6th Amendment provides all criminal defendants the right to an attorney. It’s hard to be logical amid so much fear and anxiety. A lawyer can take the emotion out of the decision. 


So, the only solution, really, is to hire an attorney that understands the system and cares about your outcome. There is never a right choice, but there are certainly smarter ones.


Epilogue: In the end, the client accepted Chris’ advice and scheduled the matter for trial. The charges were later dismissed with the prosecutor was unable to produce all the evidence necessary to prove the case. 


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