As we have said before, criminal defense lawyers representing defendants at federal sentencing hearings must be prepared to object to unreasonable conditions of supervised release, or face an uphill battle getting them overturned.


Two lessons can be learned from the case of Carlos Manuel Del Valle-Cruz (“Cruz”). First, defense attorneys should be careful when they enter into a plea agreement with the Government that waives a defendant’s right to appeal; and, second, make sure that all objections made at sentencing are specific and detailed.


In 1997, Cruz was convicted in Oklahoma of sexual assault of a 15-year-old girl. Thirty years of age at the time, Cruz said the sexual contact (kissing and touching) was consensual. He was given a five year sentence, three of which were supervised. Following his release from prison, Cruz, as required by state law, registered as a sex offender. He subsequently moved to Florida where he failed to register as was required by that state’s laws. Over the next several years, Cruz was arrested twice for failing to register and received relatively minor sentences. In 2009, he moved to Puerto Rico where he once again failed to register as he was required to do under that territory’s law. This led to Cruz being indicted in 2012 under the federal sex offender registration law known as “SORNA.”


Cruz entered into a plea agreement with the Government. The agreement contained a general waiver of appeal clause that stated: “[T]he defendant … waives and permanently surrenders his right to appeal the judgment and sentence in the case. An expedited Presentence Investigation Report was prepared. The report was disclosed to Cruz’s counsel on December 11, 2012. The trial court conducted a sentencing hearing the following day. An appeal decision by the First Circuit Court of Appeals issued on April 6, 2015 did not explain the extraordinary haste between issuance of the presentence report and the sentencing hearing. The trial court sentenced Cruz to 21 months in prison with an additional seven years of supervised release. The court attached a host of conditions to the supervised release.


From the host of conditions imposed by the judge in the Cruz case, only two were ultimately dealt with by the First Circuit: 1) that Cruz would have to participate in mental health and sex offender treatment, including submission to polygraph and PPG testing (attaching a pressure-sensitive device around a man’s penis, showing him an array of erotic child pornography, and measuring his level of erectile responses); and 2) that Cruz have no contact with minors under 18, would not be allowed to reside in a residence with a minor, and would not work or volunteer with minors. Further, the judge ordered that Cruz could not have any contact with minors “unless approved in advance by the U.S. Probation Officer.” The latter condition was particularly crippling because Cruz has a son who was nine-years-old at time of sentencing.


These two conditions are clearly draconian. Cruz had one “sex offense” in his record—the 1997 groping and feeling of a 15-year-old co-worker. In his more than a decade of freedom between 1999 and 2012, he never had an arrest or conviction for any kind of sexual misbehavior. In fact, he attended college and was in the process of obtaining a degree when arrested in 2012. At the time of sentencing, Cruz was not a pedophile by any definition—and certainly not one who should have been subjected to the kind of severe supervised release conditions imposed by the sentencing judge.


The sentencing judge did not provide any explanations for the harsh conditions. Cruz’s counsel made a general objection that the conditions were inappropriate because the original sex offense had occurred some fifteen years earlier. Counsel offered no further elaboration for the objection. He simply asked the court to “make a record” of the objection.


The first issue the First Circuit had to decide was whether Cruz’s waiver of appeal foreclosed his right to seek appellate review of his sentence.The First Circuit has established a three-prong criterion in these kinds of cases: 1) whether the scope of the waiver was clearly spelled out; 2) whether the trial court addressed the waiver with the defendant prior to sentencing; and 3) whether the denial of a defendant’s appellate rights would constitute a “miscarriage of justice.” The first two prongs of this test were met in Cruz’s case, so the only door left open for Cruz was the miscarriage of justice prong.


The First Circuit noted that the miscarriage of justice exception is frequently sought but seldom applied. The appeals court has granted this exception only in cases where the “constitutional dimension” is clear and the government would suffer “little prejudice” by its application. Against this backdrop, the First Circuit entertained but rejected the mental health/sex offender condition, but elected to apply the exception to the condition barring Cruz from having any contact with minors.


The First Circuit followed the lead of the Third, Seventh and Eighth Circuits which have held that a condition barring contact with minors without explanation warrants resentencing. The First Circuit held:


“The record before us is devoid of any explanation for the imposition of conditions that would deprive Del Valle-Cruz of any meaningful relationship with his son. The imposition of these conditions – justified by neither the government nor the court – was a significant error. Although a court’s failure to explain its reasoning for the imposition of conditions does not automatically result in a miscarriage of justice, where, as here, the error is of this constitutional dimension, there can be no doubt that the enforcement of the [appeal] waiver would be a miscarriage of justice.”


It is incongruous that a sentencing judge would impose the kind of draconian conditions imposed on Cruz without providing any justifiable explanation. Given Cruz’s criminal history, there was no reasonable justification for imposing either condition addressed by the appeals court, or most of the other conditions imposed by the judge.


A defendant’s decision to waive his right to appeals always comes before the presentence report is issued. Counsel should insist on preserving the right to appeal both unlawful and unreasonable conditions of supervised release in any plea agreement. Failing to do that, counsel should make a detailed and specific objection to any supervised release condition that is either unlawful or unreasonable. Counsel should also insist that the sentencing judge provide detailed explanations for each condition attached to supervised release. The failure of counsel to offer a more elaborate objection confined Cruz’s appellate review under the strict “miscarriage of justice” standard. The waiver of the right to appeal should always be conditioned on the defendant maintaining his right to appeal any unlawful or unreasonable conditions of supervised release.