[Note from co-editor-in-chief Ryan Goodman: 

I spoke with Thomas Green, Senior Counsel at Sidley Austin, and an attorney who has had an extraordinary practice in white collar criminal defense work. Green formerly managed Sidley’s federal and state investigation and white collar defense practice group and has represented clients in some of the nation’s most important criminal prosecutions over the last half century.

With the advent of federal and state indictments of former President Donald Trump and dozens of indicted and unindicted co-conspirators, some of whom may decide to cooperate with prosecutors, I turned to Green for his analysis. I asked Green under what circumstances, in general, he would advise a client to consider pleading guilty, what kinds of factors he would discuss with his client to help them decide what is in their best interests, and how that process plays out.]

Green’s response follows.]

Keep in mind that a lawyer is normally retained by a white collar defendant very soon after the client learns he is under investigation.  The lawyer will then follow the course of the investigation, often utilizing joint defense agreements, in order to understand the scope and contours of the government’s accumulating evidence as it relates to the events under scrutiny.  In this process the defense lawyer should have a distinct advantage: he has access to his client, and presumably his client knows the facts surrounding the subject matter of the investigation.  But getting his client to reveal the true facts is often an arduous task.  White collar defendants are often reluctant to confide in their lawyer and they are typically adept at rationalizing their conduct to the point that they are simply unable to admit that they did anything wrong.  Hopefully, over time, the lawyer will develop an intimate relationship with his client, and, better yet, with members of his family as well.  As trust develops between lawyer and client, the lawyer embarks on a process, part psychological and part reality testing, to induce the truth from the client.

Simultaneously the lawyer must continually examine the government’s emerging case to find and assess all potential factual and/or legal flaws.  Either before or after indictment, there comes a point in this process where the lawyer is in position to weigh the government’s evidence against his ability to contest and rebut that evidence in the courtroom, which includes an assessment of the strength of the client’s evidence and his demeanor and the impact both will have on a jury.  There are a number of reasons why a client could be persuaded to consider pleading guilty.  Personal finances, health, family welfare and the possibility of severe punishment are among them. But I have also resorted to considerations touching on religion, atonement, integrity and courage.

Still, the overriding consideration in my calculus is whether I have reached the conclusion that we are so unlikely to prevail at trial that the only way for the client to improve his position is to consider pleading guilty under a heavily negotiated agreement. Nevertheless, my assessment never controls; the decision belongs to the client or to the client and his family.  As difficult as the process may have been to secure the truth from the client, it often pales by comparison to the process of bringing the client to stand before the court and admit his guilt.  There are times at this moment when everything breaks down, and whether Humpty Dumpty can be put together again is often in doubt.  Extraordinary hand holding by the lawyer may be required, and long discussion about the client’s need to focus on his own destiny (and that of his family) rather than misguided notions of loyalty are part of the process to try to revive the plea process.  Throughout all of this, I am acutely aware that all I can do is to give advice.  More often than not, my advice is ultimately embraced by my client.  But if not, and absent an irreparable breakdown between us, the client’s decision to proceed to trial will be honored.


Editor’s note: Just Security is publishing this article alongside Katya Jestin, Marcus A.R. Childress and Caroline M. Darmody, A Letter to Kenneth Chesebro on Pleading Guilty, September 7, 2023

IMAGE: Gavel with American flag in background (via Getty Images)