Yesterday, appeared as an expert witness in the United States District Court for the Middle District of Tennessee on a 2255 hearing that involved a question of ineffective assistance of counsel at the plea bargaining stage. Essentially, the question for the Court was whether counsel’s advice led to Federal jury trial that should never have taken place. The Supreme Court held in Lafler a few years ago that there is the right to effective assistance of counsel at the plea bargaining stage — which makes sense. The criminal justice system is a system of pleas more so than a system of trials. This is particularly the case in Federal court where jury trials are rare. In the wake of Padilla and other cases, plea bargaining is a high stakes game with which comes a host of collateral consequences. I don’t make it a practice to comment directly here on the cases in which I am involved. So, I won’t do so here. However, my preparations for court yesterday caused me to reflect on some of the pitfalls criminal defense practitioners fact. And many of those pitfalls come from the curious intersection of criminal law and procedure and the mindset of the criminal defendant. I imagine the issues to involve three C’s — certainty, clarity, and completeness. All of these things sound easy on paper but are nearly impossibly complex in the trenches.

• Certainty — There was an old joke in law school that all legal questions yield a single answer. And that answer is as follows: “that depends.” All clients and families are caught up in the trauma of the circumstances, even if that trauma is of their own making. And they seek certainty in their most essential questions. These are some but not all of the questions for which certainty is nearly impossible: What are my chances? Can you win this case? How can they go forward against me when they only have her claim about what I did but “no evidence” of my guilt? How long will this case take? Can’t you prove he’s lying? Worst case, what is going to happen to me? Best case, what is going to happen to me? Can you get me out of this? Clients will ask these questions, and you will say “It depends.” You will have a discussion. And a week later you will have the same discussion. They will then rephrase the question MMPI style. And if they don’t like your answer, they will sometimes seek to wear you down until you give a different response that soothes. Of course, you cannot spin reality to shape your words. And the temporary relief you experience from just saying what they want to hear will always revisit you ten-fold in misery when the case reaches its conclusion, particularly if the conclusion is unsatisfactory. “But Mr. Key, you told me ….” Key’s maxim number one: “never ever use the language of certainty when you are in an uncertain landscape.” If you think you’re right about the law and the State is wrong, you can say so. But you must do so with the additional proviso that the judge can and often does rule with the State when the State is wrong.
• Clarity — But where the law provides clarity, you should so state the law. If a client is charged with two offenses for which the range of punishment is 1-20 years to serve, you should tell the client that he can expect a potential sentence of as little as a single year of probation or as much as 40 years to serve in prison. And you will not know the sentence until it is imposed. If you are taking a plea to ten years to serve in which the client will have parole eligibility, you should tell the client that parole is a matter of grace. You cannot say when or if the client will be paroled and that, in taking a plea to ten to serve he should be prepared for the possibility of serving every day of ten years on prison. Key’s Second Maxim: “where the law offers clarity, you should offer it, particularly where the clear possibility paints the bleakest landscape.” 
• Completeness — Your advice should be complete and comprehensive. Yes, this seems an obvious point. Yes, this seems like a truism. But keep in mind, Key’s Third Maxim: Never provide legal advice where the environment does not allow for the giving of a complete answer. What do I mean by this? If the answer is better rendered in writing than orally, then do not try to answer without putting the answer in writing. And the answer should just about always be reduced to writing. Do not allow your opponent or the court to box you into a situation where the client has minutes to make a dramatic life-altering decision. Be mindful of the environment in which the question is posed, and be willing to refrain from answering the question until you can enter into the appropriate environment. A text message is virtually never the right environment to discuss a complex client matter. If circumstances allow for anything less than a complete response, then do not attempt a response. And if you have any doubts regarding whether the environment is proper for giving complete advice, then you are likely in the wrong environment.

Plea bargaining is tricky because often the biggest hindrance to you doing an effective job in explaining the plea is the client herself and her mental or emotional status. The client craves positive news and will sometimes push you to be more positive than you can be at the moment or ever. Which leads to Key’s Fourth Maxim: practice as if the glass is half full but advise as if it is half empty. In your preparation, presentations, and negotiations, you should be confident and positive in your abilities and command of the law. Be unstoppable in the courtroom. But in the conference room be candid and maybe even a little pessimistic.