Hochstadt v. N.Y. State Educ. Dep’t, 2013 U.S. App. LEXIS 19418 (2d Cir. Sept. 19, 2013):

We review "for abuse of discretion a district court's decision to grant or deny an extension of time to file a notice of appeal." Williams v. KFC Nat'l Mgmt. Co., 391 F.3d 411, 415 (2d Cir. 2004). Pursuant to Federal Rule of Appellate Procedure 4(a)(5)(A), the district court may extend the thirty-day window to file a notice of appeal if a "party shows excusable neglect or good cause." In Pioneer Investment Services Company v. Brunswick Associates Limited Partnership, 507 U.S. 380, 395 (1993), the Supreme Court set forth four factors to be considered when a party asserts "excusable neglect" as justification for missing a judicial deadline. These factors are: "(1) 'the danger of prejudice' to the party opposing the extension; (2) 'the length of the delay and its potential impact on judicial proceedings'; (3) 'the reason for the delay, including whether it was within the reasonable control' of the party seeking the extension; and (4) whether the party seeking the extension 'acted in good faith.'" In re Am. Exp. Fin. Advisors Sec. Litig., 672 F.3d 113, 129 (2d Cir. 2011) (quoting Pioneer Inv. Servs. Co., 507 U.S. at 395). "While th[e]se  [*3] factors are the central focus of the inquiry, the ultimate determination depends upon a careful review of 'all relevant circumstances.'" Id.

Here, Penkovsky sought an extension of time to file his notice of appeal on May 18, 2012 -- thirty-eight days after the district court's April 10, 2012 order imposing sanctions. Penkovsky stated that he had been unable to file a notice of appeal within thirty days because, on May 2, 2012, his former spouse received an eviction notice and his attention subsequently became "almost entirely focused" on that matter. In applying the Pioneer factors to the instant appeal, we conclude that the opposing party arguably would not have suffered prejudice if the extension had been granted (as the sanctions were payable to the district court). However, at least two of the Pioneer factors favor the district court's denial of Penkovsky's motion. Specifically: (1) an extension to file a notice of appeal -- a document that simply needed to identify what orders Penkovsky sought to appeal -- would have only further delayed the resolution of this case, which has been ongoing since 2008; and (2) the reason for Penkovsky's delay related to an incident occurring from May  2, 2012 onward, leaving him twenty-two days before that date to file a timely notice of appeal, an opportunity Penkovsky does not explain foregoing. As to the fourth Pioneer factor, we simply note that Penkovsky consistently failed to comply with the district court's orders and, for over sixteen months, did not pay the sanctions imposed on him until the district court warned him that he would be arrested barring payment. Accordingly, considering "'all relevant circumstances,'" it cannot be said that the district court abused its discretion in denying Penkovsky's motion for an extension of time to file his appeal. In re Am. Exp. Fin. Advisors Sec. Litig., 672 F.3d at 129 (quoting Pioneer Inv. Servs. Co., 507 U.S. at 395).