Herring v. United States of America
Jeffrey Herring v. United States of America; United States of America v. Jeffrey Herring
- Kenneth Karas
- 7:20-cv-09752
- U.S. District Court · Southern District of New York
- 22
In Jeffrey Herring v. United States, Judge Karas dismissed Herring’s challenge to his conviction with prejudice, rejecting both claims.
Jeffrey Herring’s federal conviction and sentence remain in place; the United States prevailed on his § 2255 petition.
What happened
In Jeffrey Herring v. United States of America, Jeffrey Herring asked the court to set aside his conviction, arguing that his lawyer mishandled plea discussions and that Hobbs Act robbery was not a qualifying violent crime. Herring represented himself in this proceeding.
The court found that Herring provided no reliable evidence of a 20-year cooperation plea offer or that he would have accepted it. It also held that controlling Second Circuit law treats completed Hobbs Act robbery as a violent crime for the firearm-related conviction.
Judge Kenneth M. Karas dismissed the petition with prejudice, entered judgment for the United States, closed the civil case, and declined to issue a certificate allowing an appeal.
The detailed version
- Herring v. United States of America · No. 7:20-cv-09752
- Kenneth Karas
- Nov. 6, 2025
Background
Jeffrey Herring filed a motion under 28 U.S.C. § 2255 asking the court to vacate, set aside, or correct his federal conviction. He proceeded without a lawyer. The motion was filed in connection with his civil case, No. 20-CV-9752, and his criminal case, No. 16-CR-302.
A jury convicted Herring on all five counts charged in the superseding indictment, including robbery-related offenses, racketeering conspiracy, murder through use of a firearm, and murder in aid of racketeering. The court sentenced him to life plus five years in prison and imposed a $500 mandatory special assessment. The Second Circuit later affirmed his conviction on direct appeal.
Claims and analysis
Herring raised two claims. First, he argued that his lawyer was ineffective during plea discussions. Herring claimed that the government had made a verbal offer allowing him to plead guilty, cooperate against codefendants, and face a maximum sentence of 20 years. He also claimed that counsel failed to explain the benefit of a possible three-level reduction for accepting responsibility.
The court rejected this claim without holding a hearing. Defense counsel submitted a sworn statement saying that the government never made a plea offer and never agreed to a cooperation arrangement or a 20-year sentence. The court also relied on the record showing that the other defendants had already pleaded guilty or were about to do so by the time Herring claimed the offer was made. In addition, the court noted that the government’s stated practice was to make plea offers in writing and that the other cooperation agreements were written.
The court concluded that Herring’s unsupported account was contradicted by counsel’s affidavit and the case record. It also held that Herring failed to show prejudice—a reasonable likelihood that better advice would have changed the result. Herring’s claim that he would have accepted the offer was not supported by objective evidence and conflicted with his sworn trial testimony denying involvement in the robbery and murder. The court further reasoned that, even assuming a 20-year plea offer existed, the proposed three-level reduction would not have lowered the sentence below the applicable 20-year statutory maximum for the robbery counts.
Second, Herring argued that Hobbs Act robbery does not qualify as a “crime of violence” under 18 U.S.C. § 924(c)(3)(A). The court rejected that argument as contrary to controlling Second Circuit precedent. It explained that the Second Circuit had already rejected Herring’s argument on direct appeal and had continued to hold that completed Hobbs Act robbery qualifies as a crime of violence. The court also stated that a later Supreme Court decision invalidating a different, residual definition of “crime of violence” did not affect the provision relevant to Herring’s conviction.
Disposition
The court stated that the petition was denied and concluded that it was dismissed with prejudice. It directed the Clerk to enter judgment for the United States in the civil case, close that case, terminate the pending motions in the criminal case, and send Herring a copy of the opinion. The court also declined to issue a certificate of appealability and certified that an appeal from the judgment on the merits would not be taken in good faith.
Read the full 22-page opinion on CourtListener, the free public archive maintained by the Free Law Project.