On June 5, 2017, in an opinion with facts that even the Court seemed to recognize read like the script for a straight-to-video movie, the Second Circuit (Jacobs, Sack, Carney) declined to overturn a defendant’s conviction and 35-year sentence despite the fact that the defendant’s counsel had engaged in an alleged sexual relationship with the defendant’s mother contemporaneously with his representation of the defendant, arguably creating an impermissible conflict of interest in violation of the Sixth Amendment. The Second Circuit deferred the issue of whether the relationship in fact infringed on the defendant’s right to conflict-free representation, reasoning that post-conviction collateral review provided a better avenue to develop a factual record as to the nature and extent of the alleged affair and its impact, if any, on the defendant’s decision to plead guilty.

1. Factual Background

Defendant-appellant Jonathan DeLaura registered with the New York State Sex Offender Registry, following DeLaura’s 2009 guilty plea in Bronx County court for sexual misconduct with a minor.

Law enforcement agents began again investigating DeLaura in 2011 after linking his IP address to child pornography files that DeLaura had shared on a peer-to-peer internet network. The agents learned that DeLaura also posed as a teenage girl in an Internet chat room to trick adolescent boys into sending him nude photos of themselves. He pressured at least one of his victims to meet him in person on multiple occasions under threat that DeLaura would publicize the photos. The Putnam County Sheriff’s Department arrested DeLaura during a sting operation, and the U.S. Attorney’s Office for the Southern District of New York charged DeLaura with receiving and distributing child pornography over the Internet, possessing child pornography, and sending obscene material to a 15-year-old.

DeLaura has an extensive history of childhood abuse.

2. Procedural History

Linda DeLaura, the defendant’s mother, retained an attorney named Gary Greenwald to represent the defendant in connection with the SDNY prosecution. Greenwald received $25,000 for his services, and shortly thereafter DeLaura expressed an interest in pleading guilty to all charges. “Then the plot thickened.” Slip Op. at 5.

During the plea negotiations, federal prosecutors contacted District Judge Kenneth Karas, who was presiding over DeLaura’s case, to inform him that they had received information “the nature of which is quite personal” indicating that Greenwald’s representation of DeLaura presented a conflict of interest. Id. In an in-chambers discussion with Judge Karas and Greenwald, the prosecutor explained that he learned Greenwald had begun a “non-platonic” relationship with DeLaura’s mother, and that Greenwald may have forgiven “significant legal fees” because of this relationship. Id. at 6–7. When confronted with the prosecutors’ suspicions, Greenwald coyly answered some questions but refused to answer others, leaving prosecutors with the impression that “the information [they] had received was . . . correct.”

In keeping with Second Circuit law, a court that is “apprised of even the possibility of a conflict of interest,” has an “inquiry obligation” to “investigate the facts and details of the attorney’s interests to determine whether the attorney in fact suffers from an actual conflict, a potential conflict, or no genuine conflict of all.” Id. at 8 (quoting United States v. Levy, 25 F.3d 146, 153 (2d Cir. 1994)). Only after such an “inquiry”—known as a Curcio hearing—may a defendant waive any actual or potential conflicts of interest, or ask for new counsel. Id. at 8–9.

Judge Karas appointed for DeLaura an independent counsel for purposes of conducting the requisite inquiry into the prosecutors’ allegations. At the conflicts hearing, with DeLaura present, Judge Karas and prosecutors reiterated the possible conflicts that could ensue from Greenwald’s continued representation of DeLaura:

(1) because the relationship ended, Greenwald might bear a grudge against DeLaura or might want to spend as little time with him as possible.

(2) given the ethical and personal problems with the relationship, Greenwald might have an interest in “mak[ing] nice to the government so that it would not report him to the disciplinary committee, or so that the relationship would not become public; and

(3) that the fee arrangement could somehow have been based on the relationship, and that Greenwald might have an interest in ending the representation quickly once he was no longer being compensated.

Id. at 7 (record citations omitted). But in an “eyebrow-raising” exchange with Judge Karas, Greenwald again refused to answer any questions about the alleged relationship, instead suggesting that Judge Karas could deduce the answers from the plot of the 2000 film The Contender, in which a female candidate for U.S. Vice President is confronted with allegations about her sexual history. Id. at 7–8. The appalled Judge Karas, said: “You won’t deny it. You won’t deny it. You want to invoke a movie, that’s fine. So let’s have the hearing.” Id. at 8.

In the end, however, Greenwald’s “intransigence” prevented the court from making any factual findings about the existence or extent of his interactions with Linda DeLaura. At an impasse, Judge Karas asked DeLaura to proceed under the hypothetical assumption that the allegations were true, and then asked if he wished to waive any conflicts the assumed facts might create. DeLaura indicated that he did, and Judge Karas accepted DeLaura’s waiver.

Soon after, DeLaura executed a plea agreement that contained a broad waiver of his right to appeal or otherwise collaterally attack his conviction or sentence. Judge Karas sentenced DeLaura to a 420-month term of incarceration. DeLaura, with new counsel, brought the instant appeal on the grounds that Greenwald was ineffective because of the possible conflict of interest. Greenwald died while the case was pending before the Second Circuit Court of Appeals.

3. Decision on Appeal

The Second Circuit affirmed DeLaura’s conviction. Writing for the court, Judge Jacobs explained when criminal defendants raise issues of ineffective assistance of counsel in their direct appeal of their convictions or sentence, appellate courts may (1) “decline to hear the claim,” (2) “remand to the district court for necessary factfinding;” or (3) “decide the claim on the record.” Id. at 12 (quoting United States v. Adams, 658 F.3d 219, 226 (2d Cir. 2014)). Despite having “qualms about a possible conflict,” the Second Circuit concluded that DeLaura’s claim of ineffective assistance could not “reliably be decided on the present record.” Id. at 11–12.

Resolving DeLaura’s appeal would require the court to engage in a two-step inquiry: first evaluating the validity of DeLaura’s waiver of the conflict of interest, and second—if his waiver is found deficient—considering whether DeLaura was prejudiced by the conflict. Id. at 12. But the Second Circuit pointed out that the record before the court allowed it to answer few of the questions presented by DeLaura’s challenge: for example, the court did not know “whether there was a sexual relationship (or its timing, duration, or terms), whether a conflict arose from it, whether that conflict was so severe as to be unwaivable, or whether Delaura was harmed by it.” Id. at 13. This decision is consistent with the Supreme Court’s expressed preference for resolving ineffectiness claims on collateral review. Id. (citing Massaro v. United States, 538 U.S. 500, 504 (2003). The Court, therefore, affirmed.[1]

4. Commentary

The Court’s ruling reflects the limited willingness of the Court to reverse a conviction or even to grant a remand for fact-finding on direct appeal. Even where the defendant’s lawyer appears to have had a sexual relationship with the defendant’s mother, perhaps in exchange for a reduced fee, the Court preferred to allow the defendant to raise the claim in a separate habeas petition. To be sure, the record could be better developed—it almost always can be better developed, given that the purpose of trial court proceedings is not to identify and explore possible ineffective assistance of counsel. But even so, the record here was compelling, and yet still insufficient.

What can counsel learn from this? A decision whether to raise an ineffectiveness claim in the post-Masaro environment calls to mind the comment about throwing a pass that is attributed to the late football coach Woody Hayes: three things can happen and two of them are bad. A defendant who raises an ineffectiveness claim on direct appeal faces three outcomes: the claim can be denied, delayed or granted. Only the last of these—the least likely—is a positive outcome, and it is uncommon, even where, as here, the facts are suggestive of ineffectiveness. The first outcome is possible, especially if the Court can rule that the defense lawyer acted reasonably because the foregone argument would have been rejected. The second possible outcome—neither rejecting nor accepting the appeal, but leaving it for a habeas petition—leaves the defendant no better off than if he or she had waited to bring a habeas petition. In essence, the real risk of rejection, balanced against the low likelihood of success, make deferring an ineffectiveness claim until a habeas petition the best choice. It is no wonder that some appellate counsel elect not to press an ineffectiveness claim on direct appeal.

The case also emphasizes the importance of evidentiary hearings to the resolution of many ineffective-assistance claims, regardless of the court in which the defendant was convicted. In this case, the Second Circuit applauded Judge Karas’s “resourceful expedient” of asking DeLaura to presume the existence of the conflict of interest and inquiring whether he wished to waive that hypothetical conflict. See Slip Op. at 9. Given that there is no right to counsel in the context of a habeas petition, the Massaro expedient of waiting for a habeas petition puts the defendant in a difficult spot. A remand by the Circuit would allow the defendant to have the assistance of court-appointed counsel in securing relief. There is an irony to the current state of affairs: DeLaura, having been likely denied conflict-free and effective assistance of counsel, must demonstrate that his right were denied in a habeas proceeding without the assistance of counsel.

Finally, we see a divergence between the Supreme Court’s ruling in Massaro, which seems to favor hearings, with its decisions that greatly limit the availability of evidentiary hearings in federal habeas cases involving state prisoners in recent years. Since the 2011 case of Cullen v. Pinholster, 131 S. Ct. 1388 (2011), district courts must accept the factual predicate for the state court’s decision, even if information gleaned after the state proceedings proves a petitioner’s claim and justifies granting the petition. The Supreme Court determined in Pinholster that the “highly deferential” standard codified in 28 U.S.C. § 2254(d)(1) limits the scope of federal habeas review to the reasonableness of the state court’s denial of a prisoner’s claims based on the same evidence that the state court had before it at the time it adjudicated the claims on the merits. Id. at 1398. However, because of the nature of ineffective assistance of counsel claims, allegations concerning an attorney’s delinquent performance are often not clearly reflected in the trial record, and defendants cannot raise effective challenges to their trial counsel on direct appeal for the reasons highlighted by Judge Jacobs in this case. But as noted, with no constitutional right to counsel in post-conviction challenges, many defendants lack a meaningful opportunity to perfect their records in time to file for state habeas relief. Absent counsel, practical impediments—such as incarceration—hinder defendants’ ability to reinvestigate their cases to support an ineffective assistance of counsel claim. In turn, this affects the viability of obtaining relief through a federal petition for habeas corpus. Differences between state and federal post-conviction proceedings challenging ineffective assistance of counsel put state court defendants in an even more difficult position than are federal court defendants.