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New York Law Journal Might There Be a Broader Message in the Bolton Plea Deal? By: John E. Jones III and Joel Cohen To begin, two things can be true at the same time. One, John Bolton was indicted because he is indeed considered by the president to be an enemy. Two, the Bolton indictment, unlike investigations initiated against other Trump “enemies”, was justifiable. He had secretly secured classified information while he was National Security Advisor in order to later write a book. He forwarded his computerized notes to the unsecured computers of his wife and daughter in order to (a) be able to wipe his own computer free of the stolen secrets, (b) maintain access to the information after he left the first Trump Administration and (c) safely hide what he had done. That said however, there seems to be nothing overwhelmingly unique in the Bolton plea agreement. Typically, the Justice Department reaches an executed plea agreement with a defendant under which the defendant will be exposed to a potential jail sentence of a particular range of time – say, e.g., 12 to 18 or 33 to 41 months in jail. Notably, the judge possesses the discretion to sentence the defendant to a lesser or lengthier period than the ranges in the agreement going as high as the maximum time available under the statute. In the Bolton agreement, all there is is a maximum available time of 5 years — as under the statute to which he pleaded guilty. Thus, until a defendant appears for sentencing months later, perhaps to a longer sentence than the parties themselves expected, he simply won’t know how much time he will ultimately be required to serve. And, most importantly, he won’t be able to get his plea back if the unexpectedly lengthier sentence that the judge imposes is far longer than he had expected. As a result of this procedure, many truly guilty defendants who should plead guilty don’t because they are forced to endure a lengthy period of unnecessary uncertainty. And the principal reason for this uncertainty is that the judge cannot begin to fashion a sentence until he reviews a pre-sentence report prepared for the judge along with the parties’ advocacy submissions, which he won’t receive until long after the plea was accepted. At best at this early date, having accepted Bolton’s plea U.S. District Judge Theodore Chuang knows little more than the statutory maximum sentence—in Bolton’s case, five years. Now, there is a procedure available in the federal courts that can help to alleviate the uncertainty in the guilty plea process. It’s under Rule 11(e)(1)(c) of the Federal Rules of Criminal Procedure, where the parties can agree to a specific sentence of X months and perhaps a fine – which is not binding upon the judge unless he agrees with the sentence. So, for example, the agreement might provide for a fixed jail sentence of, say, 18 months and a fine of $200,000. When the guilty plea is entered in open court the judge tells the defendant that he will take the matter under advisement, and if he concludes that the terms are appropriate, sentence him as agreed. Conversely, he will advise the defendant that if he is unwilling to be bound by the agreement because it is too lenient, he may withdraw his plea and proceed to trial. Typically, when such agreements are authorized by the Justice Department – and they are rare — the judge does carry out the agreement that the parties proposed. So, why isn’t that procedure generally employed? Simple, many United States attorneys around the country simply don’t see it as appropriate to impose on a judge’s sentencing prerogatives, and some judges agree with that sentiment. So all there is is that under his agreement Bolton is exposed to a potential 5 years imprisonment, although it will unlikely be that high (or nearly that high). In his favor, of course, are Bolton’s age, 77, his long service to the nation, and the fact that he’s a stated “enemy” (also) of Iran who has been denied security protection by the president because the president is angry at him. Additionally, the huge fine of $2.25 million, which Bolton is to pay in full by the time of his sentencing, will be taken into account by Judge Chuang when he fashions a sentence. Still, given that there’s no binding agreement in play other than the maximum of 5 years, Bolton simply doesn’t know where he stands and to some extent is rolling the dice – even if the Justice Department prosecutor, if trusted, has whispered to his lawyer that it simply won’t be out for blood at sentencing. Federal criminal sentencing is a complex business with many moving parts. In the end, while the judge must consider certain factors and guidelines, he is fully free to reject Bolton’s likely argument that he should not be incarcerated. Indeed, he may not see the arguably sympathetic factors in play the same way – but he would undoubtedly be more likely to if a Rule 11(e)(1)(c) agreement was the procedure involved. So again, why isn’t the procedure described above used in many more cases than it is? Why are defendants and the justice system generally deprived of a better level of certainty that can easily be secured? Indeed, judges who find such agreements too imposing on the judicial process are totally free to notify the bar in their individualized court rules to not submit such agreements to them. This will allow the parties to proceed as they currently do in most cases leaving the sentence to be imposed completely in the judge’s hands on sentencing day after receiving the parties’ respective recommendations. _____________________________________________________________________ John E. Jones III is the former Chief Judge of the United States District Court for the Middle District of Pennsylvania and is the President of Dickinson College. Joel Cohen practices white collar criminal defense law at Ruskin Moscou Faltischek, PC and is the author of “Blindfolds Off: Judges on How They Decide” (ABA Publishing, 2014). Reprinted with permission from the July 1, 2026 edition of the “New York Law Journal”© 2026 ALM Global Properties, LLC. All rights reserved. Further duplication without permission is prohibited, contact 877-256-2472 or asset-and-logo-licensing@alm.com.
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