See also:United States District Court for the Southern District of New York (Carroll v. Trump, 1:22-cv-10016)

On May 9, 2023, aUnited States District Court for the Southern District of New York jury found former PresidentDonald Trump (R) liable for sexually abusing and defaming E. Jean Carroll. Trump was ordered to pay Carroll $5 million in damages.^[2][3] Kaplan presided over the case.

Following the ruling, Trump said, "I have absolutely no idea who this woman is. This verdict is a disgrace - a continuation of the greatest witch hunt of all time!"^[4]

Carroll issued a statement after the ruling, saying, "I filed this lawsuit against Donald Trump to clear my name and to get my life back. Today, the world finally knows the truth. This victory is not just for me but for every woman who has suffered because she was not believed."^[5]

In a June 2019New York Magazine article, Carroll said that Trump sexually assaulted her in the mid-1990s.^[6] At the time, Trump released a statement saying, "I’ve never met this person in my life. She is trying to sell a new book - that should indicate her motivation. It should be sold in the fiction section."^[6]

Carroll initiated the lawsuit in November 2022. The complaint said, "When Carroll’s account was published, Trump lashed out with a series of false statements. He denied the rape. Trump made additional false claims about Carroll in 2022. [...] Trump’s underlying sexual assault severely injured Carroll, causing significant pain and suffering, lasting psychological harms, loss of dignity, and invasion of her privacy. His recent defamatory statement has only added to the harm that Carroll had already suffered."^[7] The suit was brought under New York's Adult Survivors Act, a 2022 law that created a one-year window for adults who experienced a sexual offense before 2019, when the state extended the statute of limitations for civil lawsuits about certain sexual offenses, to file claims in civil court.^[8]

See also:United States District Court for the Southern District of New York (Chevron Corp. v. Donziger, 1:11-cv-00691-LAK-JCF)

On March 4, 2014, Judge Kaplan ruled in favor of Chevron, an oil and natural gas company, in a case alleging that a multi-billion dollar pollution judgment against it, issued by a foreign court, had been obtained through illegitimate means of fraud and corruption.^[9]

In the underlying case, Judge Nicolas Zambrano of Ecuador found Chevron liable for polluting the Lago Agrio rainforest on February 14, 2011, assessing about $19 billion in damages and fines against the company. Chevron refused to pay the fines or accept responsibility for the pollution, and the company brought this case on U.S. soil, alleging that much of the evidence used to obtain judgment was fabricated by lead attorney Steven Donziger. Donziger denied the allegations. Judge Kaplan disagreed; in an almost 500-page ruling, he noted, "an innocent defendant is no more entitled to submit false evidence, to co-opt and pay off a court-appointed expert or to coerce or bribe a judge or jury than a guilty one."^[9]

Judge Kaplan further noted that Donziger and his team subverted justice in their actions, writing:

Donziger pledged to appeal the ruling, calling it an "appalling decision from a deeply flawed proceeding."^[9] The appeal was heard before theSecond Circuit Court of Appeals on April 20, 2015.^[11]

See also:United States District Court for the Southern District of New York (United States, v. Ahmed Khalfan Ghailani, S10-98-cr-1023-LAK)

Judge Kaplan was the first federal judge to preside in a trial of a Guantanamo Bay detainee. On July 2, 2009, Judge Kaplan set a September 13, 2010, trial date for Ahmed Ghailani. Ghailani was charged with numerous crimes, including murder, for his involvement in the killings of 224 people and the injury of thousands more in nearly simultaneous bombings of American embassies in Tanzania and Kenya in 1998. Ghailani, a Tanzanian, was alleged to be a bomb-maker for Osama Bin Laden, though other reports stated he was a cook and bodyguard. He had been held in the facility at Guantanamo Bay since 2006. The death toll from the attacks included 12 Americans.^[12]

On November 19, 2009, the judge overturned his previous decision, finding that Ghailani did not have a right to be represented by his military defense lawyers in a civilian court. The lawyers had been reassigned by the Department of Defense although they were willing to represent the defendant, and the judge had previously allowed it. In the decision, Judge Kaplan found that Ghailani's Fifth and Sixth Amendment rights to due process and effective legal counsel would not be violated by his denial of the request. Despite so holding, the judge commented that there had been "near-insurmountable difficulties created by the U.S. government."^[13]

A jury eventually found Ghailani guilty of conspiracy to destroy government buildings, for which there was a possible sentence of 20 years to life in prison. The jury acquitted him of more than 280 other charges, including every count of murder.^[14][15]

In January of 2011, Judge Kaplan imposed the maximum sentence of life in prison. He commented that whatever Ghailani had suffered "pales in comparison to the suffering and the horror" caused by the terrorist attacks.^[14]

See also:United States District Court for the Southern District of New York (Five Borough Bicycle Club, et al., v. The City of New York, 1:07-cv-02448-LAK)

Judge Kaplan ruled on February 16, 2010, that the City of New York did not violate the First Amendment when the New York Police Department instituted a new rule that would let them ticket or arrest any recognizable group of 50 or more cyclists riding together without first obtaining a parade permit from the Police Department.^[16] One of the groups most affected was Critical Mass, an organization that held frequent bicycle protests in the city. In 2004, during the Republican National Convention, over 100 cyclists were arrested for disorderly conduct after a group of roughly 5,000 rode past Madison Square Garden in protest against former President George W. Bush.^[16]

After the law was passed, the Five Borough Bicycle Club (5BBC) sued the city in 2007, describing the process of obtaining permits as a "bureaucratic nightmare" and challenging the NYPD's assertion that it would ticket or arrest a group of 50 cyclists or more without a permit. The 5BBC asserted that the requirement violated its members' constitutional rights to expressive association, free speech, and travel; several individual plaintiffs also asserted that the NYPD retaliated and selectively enforced regulations against those who participated in rides organized by Critical Mass.^[16]

In his decision, Judge Kaplan asserted his sympathy for the cycling groups' position and their complaints about the inconvenience of the law. Nonetheless, he found that the City of New York had a sufficient interest in facilitating traffic flow and protecting the interests of those on the road, and therefore, that there was no violation of the First Amendment.^[16]

See also:United States District Court for the Southern District of New York (In re Lehman Brothers Securities and ERISA Litigation, 1:08-cv-05598-LAK)

On January 2, 2010, Judge Kaplan threw out a lawsuit involving participants of Lehman Brothers retirement plan filed against fund directors for failing to protect the plan when knowing of the deteriorating condition of the funds. Participants of the fund were seeking to recover damages after allegedly showing that directors violated theEmployee Retirement Security Act. There was not enough evidence, according to the judge's ruling, to determine if Lehman's fund managers were negligent in handling the retirement funds.^[17]

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• Judge on senior status, Southern District of New York