Following a plea or conviction, federal practitioners would almost all agree that the sentencing phase of a criminal action is the most important and consequential part of the case. In many cases, it is usually the first opportunity for the sentencing court to understand and evaluate the individual accused as a person, both good and bad, and not just a case number. A thorough attorney will begin evaluating prospective sentencing arguments from the day they take a case, regardless of whether it appears the client intends to go to trial or enter a plea. 

While it is certainly the goal to reduce the length of prison time imposed, it is equally important to evaluate and advise clients of the potential collateral consequences of sentencing, such as the amount of restitution owed or the conditions of post release supervision, among many others. Post release supervision is similar to what most people know as probation, except that it starts after a person completes their term of imprisonment. Post release supervision may include special conditions, such as drug testing, consent to home searches without a warrant, or that the person is prohibited from associating with certain people, among many other types of conditions. These “special conditions” may considerably affect a person's life after being released. 

In order to impose a “special condition,” the sentencing court must adequately justify its reasons for doing so on the record. Moreover, a special condition must “involve no greater deprivation of liberty than is reasonably necessary” to implement the statutory purposes of sentencing. United States v. Myers, 426 F.3d 117, 124 (2d Cir. 2005) (quoting U.S. Sent'g Guidelines Manual § 5D1.3(b)). 

Recently, in United States v. Jimenez, the Second Circuit reaffirmed the longstanding principle that “[a] district court is required to make an individualized assessment . . . and to state on the record the reason for imposing [a special condition]; the failure to do so is error.” Jimenez, Case No. 22-1022, *4 (2d Cir. Mar. 18, 2024) (citing United States v. Betts, 886 F.3d 198, 202 (2d Cir. 2018) and United States v. Bleau, 930 F.3d 35, 43 (2d Cir. 2019)). In Jimenez, the Second Circuit found that the sentencing court failed to adequately justify its reasons for imposing burdensome special conditions, including that the defendant participate in “cognitive behavior treatment” and complete 20 hours of community service per week while not employed, among others. You can see from Jimenez the broad authority of a sentencing court to impose “special conditions,” and the need to ensure they are justified. Ultimately, the Second Circuit remanded the case back to the sentencing court and instructed the sentencing court that it was to make an individualized finding and justified reason as to the basis for each special condition. 

The lesson from Jimenez is that best practices include the importance of challenging special conditions that a court may set.  Luckily for Mr. Jimenez, his counsel recognized the sentencing court's error and was able to succeed on appeal. The takeaway here is that advocacy at sentencing will prevent these types of errors to preserve a client's right to a fair, just and individualized sentence.