Kaplan presided over the first case where charges against Guantanamo captives were laid in a civilian court. On February 9, 2010, Kaplan ordered Ahmed Ghailani's prosecution to review the record of Ghailani's detention in the CIA's network of black sites. According to The New York Times any materials that show the decisions "were for a purpose other than national security," must be turned over to Ghailani's lawyers. Kaplan denied a motion to dismiss the charges on the grounds that due to Ghailani's long extrajudicial detention he was denied the constitutional right to a speedy trial, ruling that his extended incarceration had no adverse impact on Mr. Ghailani's ability to defend himself. This cleared the way for federal prosecutors to try him for his suspected role in Al Qaeda's 1998 bombings of U.S. embassies in Kenya and Tanzania. The New York Times reported that Kaplan's ruling could set a precedent for the cases of other Guantanamo captives, who, like Ghailani, are transferred to the civilian justice system. On January 25, 2011, Kaplan sentenced Ghailani to life, and called the attacks "horrific" and saying the deaths and damage they caused far outweighs "any and all considerations that have been advanced on behalf of the defendant." He also ordered Ghailani to pay $33 million as restitution. Working in New York City, Kaplan had been the judge in a number of federal racketeering cases involving Mafia members. In April 2010, Judge Kaplan was assigned to preside over the cases of 14 Gambino crime family members arrested on charges, among others, of racketeering, racketeering conspiracy, witness tampering, and sex trafficking of a minor. In 2016-2017 Kaplan presided over US v. Spoutz, one of the first cases of successful prosecution of attributed artwork in the United States. Eric Spoutz, an art dealer, plead guilty to one count of wire fraud related to the sale of falsely attributed artwork accompanied by forged provenance documents. Kaplan sentenced him to 41 months in federal prison and ordered to forfeit the $1.45 million he made from the scheme and pay $154,100 in restitution. Judge Kaplan also had been presiding over the environmental case brought by Ecuadorian Native groups against Texaco-Chevron. Kaplan excused Chevron from paying the judgement of the Ecuadorian courts and in turn fined the plaintiff's lawyer Steven Donziger $3.4 million for contempt and Chevron's legal fees, the largest contempt sanction in US History. Kaplan appointed private counsel to prosecute Donziger. According to The Intercept, Kaplan has written favorably about Chevron and "bypassed the standard random assignment process and handpicked someone he knew well, U.S. District JudgeLoretta Preska, to oversee the case being prosecuted by the firm he chose." Other well-known cases Kaplan has presided over at the district level include Bridgeman Art Library v. Corel Corp., Universal v. Reimerdes, , and Crandell v. New York College of Osteopathic Medicine.