JD, a 40-year-old laborer, was charged in federal court with entering the United States illegally after having been previously deported or denied entry, under 8 U.S.C. 1326. Months before his federal court charge, JD had been charged with a state court crime. He was held in custody pending his state court trial. Unfortunately for JD, the evidence in his state court case was overwhelming. The Commonwealth agreed to dismiss one of the charges, if JD agreed not to go to trial. JD saw the advantage to pleading guilty - receive a significantly lower state prison sentence.

Knowing that deportation was inevitable, he decided plead guilty early in the process. JD just hoped that the judge would impose the federal sentence "concurrently" with his state sentence. When two sentences are imposed concurrently, it means that they are served at the same time. By contrast, sentences imposed "consecutively" must be served one after the other.

Having experience in both federal and state courts, Henry knew that JD should not plead guilty to his state case first. Doing so would expose JD to a greater potential federal sentence. So, Henry and the state prosecutor agreed that JD would plead guilty to the state crime after JD plead guilty to the federal crime. Meanwhile, to place JD in a favorable light, Henry drafted a memo for the federal judge, highlighting the sentence that JD was going to receive in state court. Henry asked the federal judge to sentence JD "concurrently" with the soon-to-be imposed state sentence and to designate that JD serve his federal sentence for Illegal Re-Entry in a Massachusetts state prison.

At the sentencing hearing, the Judge expressed concern about the federal sentence running "concurrently" with JD's state sentence. The Judge questioned whether the defendant's conduct of re-entering the country illegally warranted a punishment distinct from the punishment imposed for the state crime. Henry advocated that allowing JD to serve his sentences at the same time in a state prison would save resources. Fortunately, the government agreed with Attorney Fasoldt. The judge was convinced - he sentenced JD to 90 days in prison, to be served concurrently with the state sentence in a state facility.