How the Powell and Chesebro Guilty Pleas Affect the: (1) Advice-of-Counsel Defense; and (2) Federal Case

Like many other Americans hoping for a way to save the country from the prospect of a second Trump presidency, I was heartened by last week's news that Sidney Powell and Kenneth Chesebro pleaded guilty to Georgia state charges for their efforts to undermine the 2020 Presidential election. But what about the fact that neither of them will do prison time?

Powell pled guilty to six misdemeanor charges. Under her agreement, she will serve six years of probation and will be fined $6,000. Chesebro pled guilty to one felony count and will get five years probation, a $5,000 fine, 100 hours of community service, and will eventually have his conviction expunged, which will probably enable him to continue (or, after a pause, resume) his practice of law. Both Powell and Chesebro also must write apologies (Chesebro wrote his already) and, most importantly, must cooperate in the prosecution of their co-defendants, including, insofar as they have relevant documents and testimony to offer, Donald Trump.

That last point appears to be good news. Why would the prosecution accept pleas that require only relatively light punishment for Powell and Chesebro? Presumably because they each agreed to provide testimony and/or documents that will be very useful in the case against Trump. Powell met with Trump in the Oval Office and can thus testify to Trump's statements that are relevant to his state of mind. It is not entirely clear how much, if any, direct contact Chesebro had with Trump, but he worked closely with two other defendants: Rudy Giuliani and John Eastman. The peril from documents and testimony to be supplied by Powell and Chesebro is no doubt being used by the prosecution to pressure Giuliani and Eastman--who did have considerable direct contact with Trump--to flip as well. Whether they will remains to be seen.

Even if Giuliani and Eastman don't flip, documents and testimony from Powell and Chesebro could be used to undercut the force of the advice-of-counsel defense that Trump apparently plans to offer in both the Georgia case and in special counsel Jack Smith's case against Trump in federal court in Washington, DC, where Powell, Chesebro, Giuliani, and Eastman are all unindicted co-consipirators. I'll now discuss: (1) the advice of counsel defense; and (2) the implications of the Powell and Chesebro pleas for the federal prosecution.

(1) Advice of Counsel

Prosecutors can attack the advice of counsel defense in at least five ways. First, advice of counsel is not a defense to most crimes. Where the law requires only that the defendant have intentionally acted in some way, it does not matter that the defendant believed in good faith--whether on the basis of counsel's advice or for some other reason--that the conduct was legal. If your lawyer tells you that murder isn't a crime on Halloween and you intentionally kill someone on October 31, you are guilty of murder, even if you were fool enough to believe your lawyer. However, reasonable reliance on advice of counsel can serve as a defense where the law requires corrupt intent, which is true of at least some of the charges Trump faces.

Second, some advice of counsel is so facially implausible that it provides no defense--much in the same way that "just following orders" is not a defense to war crimes where the legal obligation is clear. Suppose that Chesebro or Eastman had told Trump that Vice President Pence had the right to reject certified Electoral College votes from any state in which Pence unilaterally decided that the "Democrat governor of the state is a woke socialist, so we should have a do-over supervised by the US military." Trump could not reasonably rely on such a statement. Further, the outlandishness of the advice itself casts doubt on a defendant's sincerity in claiming to have believed it.

Third, the reasonableness and sincerity of reliance on advice of counsel can be undermined by the fact that a defendant received contrary legal advice. The lawyers providing Trump the most aggressive legal analysis were on what former Trump campaign manager Bill Stepien aptly described as "Team Crazy." One can question Stepien's self-serving description of himself as part of "Team Normal," while recognizing that an advice-of-counsel defense is surely weakened by the fact that a defendant is told by lawyers that a course of conduct is illegal but then looks for other lawyers who will tell him the opposite. Trump's cycling through Attorneys General--from Bill Barr to acting Attorney General Jeffrey Rosen to Trump's contemplation of replacing Rosen with (Georgia case co-defendant and federal case unindicted co-conspirator) Jeffrey Clark--bespeaks the intent of a defendant who was looking for a lawyer who would tell him what he wanted to hear rather than one relying in good faith on legal advice.

Fourth, the ability to rely on counsel can depend on the credibility of counsel. On this point, Chesebro's flipping is more important than Powell's because, while Powell was apparently once a respected and highly competent lawyer, by late 2020, she had pretty clearly lost touch with reality. The same can be said of Rudy Giuliani. And neither Powell nor Giuliani was ever a constitutional lawyer (as underscored by Giuliani's statement in open court that he didn't understand what "strict scrutiny" meant). By contrast with Powell and Giuliani, both Chesebro and Eastman were and are highly credentialed and knowledgeable constitutional lawyers. In form, at least, what they said was credible. Accordingly, if Chesebro can testify to the fact that everybody--including Trump--understood that the fake electors scheme was unlawful, that would be extremely useful to the prosecution in undercutting an advice-of-counsel defense.

Fifth, as a brief filed last week by Jack Smith's team argues in the federal case, presenting an advice-of-counsel defense comes with a very serious downside. Because the defense depends on the defendant's having reasonably believed what he was told by his lawyers, a defendant who presents an advice-of-counsel defense thereby waives attorney-client privilege both as to what his lawyers told him and what he said in response manifesting his mental state. The government brief and accompanying proposed order seek pre-trial disclosure from Trump of: "(1) the identity of each attorney who provided advice; (2) the specific advice given, including whether the advice was oral or written; (3) the date on which the advice was given; and (4) the information the defendant communicated or caused to be communicated to the attorney concerning the subject matter of the advice, including the date and manner of the communication."

That last point alone could mean that, even before Powell and Chesebro flipped, the advice-of-counsel defense was not very potent. If so, then the cooperation by Powell and Chesebro will mostly be relevant to the prosecution's case in chief rather than to any defense.

(2) Fifth Amendment Right Against Self-Incrimination

Suppose that Fani Willis or another lawyer on her team calls Powell and/or Chesebro to testify at trial in Georgia. They are required by their plea agreements to do so, but each of them has a realistic fear of prosecution on federal charges. They could go from unindicted to indicted co-conspirators. Accordingly, each could invoke the Fifth Amendment right against self-incrimination. What happens then?

The answer depends in the first instance on what, if anything, the full plea agreement with the Fulton County DA states with regard to this question. Failing to testify, even if to assert a valid Fifth Amendment objection, could void the agreement. For that reason, one would expect that Powell, Chesebro, and their attorneys would have at least sought use-and-derivative-use immunity for their testimony. Although Willis, acting for Fulton County and the state of Georgia, has no power to grant Powell or Chesebro any kind of immunity against federal prosecution, pursuant to the SCOTUS decisions in Murphy v. Waterfront Comm'n (1964) and Kastigar v. United States (1972), a state prosecutor's grant of immunity eliminates any Fifth Amendment privilege and precludes subsequent use and derivative use of the testimony in both state and federal prosecutions.

However, the issue is unlikely to arise in the way I've just described, because the federal case will likely go to trial well before the Georgia case. The federal trial is scheduled to begin on March 4 of next year. Powell and Chesebro exercised their speedy trial rights, which is why jury selection in their trials would have begun last week had they not pled guilty. A trial date has not been set for the other defendants. If a combination of carrots and sticks leads many of the other defendants to plead guilty following the lead of Powell and Chesebro, that could simplify the Georgia case and thus result in the trial happening sooner than it otherwise would have, but it's still unlikely to get underway before March 4. Indeed, I would not be surprised if the Georgia case does not get underway until after the 2024 election--and if Trump wins (or is otherwise installed as President via chicanery in state legislatures)--that could forestall the Georgia trial until 2029 (or forever, if, say, Trump declares himself President for Life) should the courts accept the inevitable contention that a state may not prosecute a sitting President.

Accordingly, unless I'm wrong about the timing of the Georgia case, the Powell and Chesebro guilty pleas are less valuable as Trump-stoppers than they at first appear to be. One is thus left wondering whether Powell, Chesebro, and/or possibly unindicted co-consipirators in the federal case have been negotiating immunity deals in exchange for cooperation in the federal case. Without such deals, they can certainly assert their Fifth Amendment rights. Meanwhile, the possibility of their being indicted on federal charges after all gives Smith some leverage against them. Accordingly, it would seem to be in the interest of the unindicted co-conspirators and the prosecution to strike an immunity-for-testimony deal.

Indeed, I consulted with a very experienced criminal lawyer, who explained that in the usual course of plea negotiations involving charges that overlap state and federal prosecutions, the federal prosecutors would have either signed onto the plea agreements with the state prosecutors or would have had their own agreements with the state defendants. Given the sophistication of the Willis team, the Smith team, and the defense attorneys for both Powell and Chesebro, there is thus a substantial probability that Powell and Chesebro have already agreed to testify against Trump in the federal case in exchange for immunity.

Thus, the real value of the Powell and Chesebro plea agreements may have less to do with what ends up happening in Georgia than what it tells us about their willingness to cooperate in exchange for leniency in the federal prosecution.