Modern Day Ceasar Faces Brutal End

By: James Trusty

Last week’s Second Circuit Court of Appeals opinion in U.S. v. Sinmayah Ceasar, 2021 WL 3640387 (2^nd Cir. Aug. 18, 2021) provides some insight into the challenging area of defining a “reasonable” sentence and ascertaining the circumstances when appellate courts might overturn a judge’s sentencing decision for being “unreasonably” lenient.

The case against Ceasar was not built in a day. The government obtained evidence that Ms. Ceasar was not only disseminating pro-ISIS propaganda on-line, but that she would connect likeminded Americans to ISIS travel coordinators for helping them join the fight in Syria. Ceasar was arrested at the airport, when on her way to marry an ISIS member in Sweden and then presumably to travel on to Syria. She was detained for over 16 months, but then released on strict conditions of pretrial release. Unfortunately, Ms. Ceasar returned to her on-line criminal participation, this time using a pseudonym. When the FBI came knocking, she repeatedly lied about her renewed activity as well as her deletion of thousands of texts and social media postings.

On the more sympathetic side of the ledger for this defendant was the horrific fact that she was routinely sexually abused by her father from age 4 to age 11, that her mother had gone blind, and that after spending many years in foster care, Ceasar had been subject to three “religious” marriages with physically abusive older men. Most recently, she had suffered a miscarriage and was hospitalized for suicidal ideation.

Ceasar pleaded guilty to material support of a terrorist organization, and her applicable advisory sentencing guideline range was a whopping 360-600 months. Judge Jack Weinstein, the iconic judicial rebel who passed away this summer at the age of 99, was well known for bucking the rigidity of federal sentencing guidelines. Although his decisions have been reversed a good number of times, he was widely respected as being principled, humble, innovative and honest in his approach. In this case, Judge Weinstein held a three-day sentencing hearing, complete with government and defense experts opining about whether Ceasar posed a risk upon release and describing her mindset regarding the horrific tenets of ISIS. Of particular interest to the judge was the fact that the U.S. has no established de-programming resources to directly address the thorny issue of recidivism in a terrorism context. The government correctly pointed to Ceasar’s return to ISIS propagandizing while under the watchful eye of the Court (and while pending what could have resulted in a massive period of imprisonment).

Judge Weinstein imposed a sentence of 46 months for the material support charge, adding only two months for obstruction and committing an offense while on release. He opined that she was well on her way to rehabilitation and that this sentence would “save her as a human being.” Enter the Second Circuit.

The Second Circuit reversed and remanded the case for a new sentencing. The Court sprinkled generous praise into their decision about Judge Weinstein’s integrity, but they determined that his over-emphasis on Ceasar’s rehabilitation needs (and the absence of deprogramming resources) was an abuse of judicial discretion. As federal practitioners are well aware, the U.S. Code delineates a wide range of factors for the court to consider at sentencing at 18 U.S.C. Section 3553(a), and while those factors include rehabilitation, they also require the court to weigh concepts like specific deterrence, the severity of the crime, and the likelihood of recidivism.

One of these components of federal sentencing that both prosecutors and defense attorneys routinely address is the notion of comparable cases. Reminding the sentencing judge of how similarly situated defendants were treated in other cases is a recurring exercise with both parties trying to nudge the court in their direction with either supportive examples from other imposed sentences or at least important distinctions from the opponent’s listed cases. In Ceasar’s case, the comparison game was highlighted by the recent sentencing of attorney Lynn Stewart. Ms. Stewart was a high-profile attorney who was convicted of crossing the line – passing messages between terrorists while representing one who was subject to special communication bans while in prison. Stewart’s guidelines called for a 30-year sentence, but the judge initially gave her 28 months. Like Ceasar’s case, the appellate court found the term to be unsupported and “shockingly low,” resulting in a remand and new sentencing. Stewart received 120 months, which is obviously significantly below 360 months, but the decision was upheld on appeal.

So what are we to take from Ceasar’s downfall in the Second Circuit? Are punitive appellate barbarians at the gate of individualized justice? I think not. The general deference afforded to sentencing judges who vary from the established guideline range is still intact. The appellate judges do not regularly relish deeming a lower court’s particularized decision on sentencing as an “abuse of discretion” or as “unreasonable.” The trend towards treating the guidelines as an advisory starting point, and in recognizing that their mechanical application can lead to unduly harsh outcomes is still the state of play around the federal circuits. But certain cases or circumstances are more likely to poke the appellate bear than a routine white-collar case, for instance. Material support of terrorism brings with it plenty of well-founded alarm. Rehabilitation feels particularly elusive, and the consequences of recidivism are severe—considerably more than the harm of a tax cheat or fraudster reoffending after sentencing. And the tipping point for the Second Circuit was clearly the return to ISIS employment while on release pending trial. Judge Weinstein only added two months to his sentence for that conduct, and he seemingly ignored the fact that her return to materially supporting ISIS was a powerful contradiction of defense experts who claimed she had “turned the corner” on her rehabilitative path. That particularly willful and powerful aspect of Ceasar’s behavior made it considerably easier for the appellate court to strike down an 87% downward variance from the lowest point of the advisory guideline range.

There will always be a tension between treating similar defendants similarly and the need for individualized justice, and Ceasar’s case is a good example of that challenge. But I would not expect the unique issues in this case to herald a new age of appellate overreach—terrorism cases are simply a different breed, and obstructionist behavior while the case is pending–bad for any defendant at sentencing–is exponentially more troublesome in a material support prosecution context.