CITGO Petroleum Corp. v. Ascot Underwriting Ltd.

Court of Appeals for the Second Circuit·Decided October 28, 2025·No. 24-0227-cv·Published

Opinion

24-0227-cv CITGO Petroleum Corp. v. Ascot Underwriting Ltd. et al.

UNITED STATES COURT OF APPEALS FOR THE SECOND CIRCUIT

August Term 2024

Argued: January 24, 2025

Decided: October 28, 2025 Docket No. 24-0227-cv

CITGO PETROLEUM CORPORATION, Plaintiff-Appellee,

v.

ASCOT UNDERWRITING LIMITED, for and on behalf of Lloyd's Syndicate 1414, PIONEER UNDERWRITING LIMITED, for and on behalf of Syndicate 9146, MS AMLIN UNDERWRITING LIMITED, for and on behalf of Lloyd's Syndicate 2001, TRAVELERS SYNDICATE MANAGEMENT LIMITED, for and on behalf of Lloyd's Syndicate 5000, BRIT SYNDICATES LIMITED, for and on behalf of Lloyd's Syndicate 2987, SOMPO INTERNATIONAL INSURANCE, for and on behalf of Lloyd's Syndicate 5151, CHAUCER SYNDICATES LIMITED, for and on behalf of Lloyd's Syndicate 1084, MARKEL SYNDICATE MANAGEMENT LIMITED, for and on behalf of Lloyd's Syndicate 3000, NEON UNDERWRITING LIMITED, for and on behalf of Lloyd's Syndicate 2468, STARSTONE INSURANCE SE, Defendants-Appellants.

ON APPEAL FROM THE UNITED STATES DISTRICT COURT FOR THE SOUTHERN DISTRICT OF NEW YORK

Before:

CHIN, PÉREZ, and NATHAN, Circuit Judges.

Appeal from a judgment of the United States District Court for the Southern District of New York (Woods, J.) awarding $54.2 million in damages plus interest to the insured in an insurance coverage dispute over a cargo of crude oil seized by Venezuelan authorities. The policy at issue provided coverage for certain war-related risks, including for losses arising from "insurrection," and the insured asserted that it was entitled to coverage for the lost cargo because the attendant political conditions in Venezuela constituted an insurrection within the meaning of that provision. On cross-motions for summary judgment, the district court ruled that an insurrection had occurred within the meaning of the policy, and the case proceeded to trial on the issues of causation and damages. The insured prevailed at trial, and the reinsurers appeal, challenging the district court's summary judgment decision, orders on judicial notice, and jury instructions on the issue of causation.

AFFIRMED.

DAVID F. KLEIN (Richard P. Donoghue, Mark J. Plumer, John P. Chamberlain, and Jeffrey W. Mikoni, on the brief), Pillsbury Winthrop Shaw Pittman LLP, New York, NY, and Washington, D.C., for Plaintiff-Appellee.

JOHN M. WOODS, Clyde & Co US LLP, New York, NY, for Defendants-Appellants.

CHIN, Circuit Judge:

In this insurance coverage dispute, Venezuelan authorities seized nearly a million barrels of crude oil from a cargo ship under the threat of force. The oil was insured under a policy (the "Policy") that provided coverage for loss caused by, inter alia, an "insurrection." The insured -- plaintiff-appellee CITGO Petroleum Corporation ("CITGO") -- submitted a claim, asserting that the political conditions in Venezuela leading up to the seizure constituted an insurrection within the meaning of the Policy. Defendants-appellants reinsurance companies (the "Reinsurers") 1 disagreed and denied coverage, leading to the instant litigation and appeal.

1 The parties to the Policy are somewhat different from the parties to this litigation and appeal because of the involvement of other non-party insurance companies in the insurance relationship, but it is undisputed that CITGO could pursue its insurance claims directly against the Reinsurers.

On cross-motions for summary judgment, the district court ruled in favor of CITGO and held as a matter of law that an "insurrection" within the meaning of the Policy had occurred. The case proceeded to trial on the issues of causation and damages.

After a five-day trial, the insured prevailed on three of four issues presented to the jury, and judgment in the amount of $54,235,187.24 plus interest was entered in favor of CITGO. The Reinsurers now appeal, challenging the district court's summary judgment decision, orders on judicial notice, and jury instructions on the issue of causation. For the reasons set forth below, we conclude that the district court did not err or abuse its discretion in any of the challenged rulings, and we AFFIRM.

BACKGROUND

This appeal involves rulings at two different stages of the litigation below: the district court's summary judgment decision concluding that there was an "insurrection" and the district court's jury instructions on causation. As to the challenge to the summary judgment decision, we accept the undisputed and indisputable facts and otherwise construe the evidence in the light most favorable to the Reinsurers, as the parties opposing summary judgment, and we

draw all reasonable inferences in their favor. See Gary Friedrich Enters., LLC v. Marvel Characters, Inc., 716 F.3d 302, 312 (2d Cir. 2013); Green v. Town of E. Haven, 952 F.3d 394, 407 (2d Cir. 2020). As to the challenges involving the trial, we construe the evidence in favor of the prevailing party -- here, CITGO. See Saint- Jean v. Emigrant Mortg. Co., 129 F.4th 124, 133 (2d Cir. 2025). I. The Facts A. Venezuelan Politics In October 2012, Venezuela's longtime leader Hugo Chávez was reelected to a six-year term as president. But after Chávez died five months later, his then-vice president, Nicolás Maduro, stepped in as interim president. Maduro was elected to serve out the remainder of Chávez's term.

By 2015, the political landscape in Venezuela had shifted, and a coalition of Maduro's political opponents won control of the National Assembly, Venezuela's main legislative body. In response, Maduro's supporters began targeting the National Assembly and its members, including by raiding National Assembly buildings and physically attacking and imprisoning politicians from the opposition. As his supporters launched several such attacks over the next

few years, Maduro used his power to arrest and prosecute politicians from the opposition.

In May 2017, tensions escalated after Maduro issued Presidential Decree No. 2830, which called for elections to establish a "National Constituent Assembly" separate and apart from the existing National Assembly. In the face of the ensuing mass protests, Maduro stated:

We will go into combat. We will never surrender. What could not be done with votes, we will do with arms. We will liberate our nation with arms.

Confidential Deferred Joint Appendix ("Conf. App'x") at 97. Meanwhile, in the United States, these events prompted then-President Donald Trump to impose sanctions on Venezuela and decry the "establishment of an illegitimate Constituent Assembly, which has usurped the power of the democratically elected National Assembly," and the "ongoing repression and persecution of, and violence toward, the political opposition." Id. (quoting Exec. Order No. 13808, 82 Fed. Reg. 41155 (Aug. 24, 2017)).

About a year later in May 2018, Maduro called for snap presidential elections and won. On January 23, 2019, however, the National Assembly declared Maduro's reelection to be illegitimate and declared its president, Juan

Guaidó, to be the legitimate interim president of Venezuela until free and fair elections could be held. Maduro nevertheless refused to cede control over the instruments of state power, preventing Guaidó from exercising authority within the country.

The United States refused to recognize the results of the 2018 election. On the same day that the National Assembly declared Guaidó to be interim president, President Trump and Secretary of State Michael Pompeo issued statements recognizing Guaidó as the legitimate leader of Venezuela. And later that month, on January 25, 2019, President Trump issued another executive order in which he further criticized the Maduro regime and extended the existing sanctions on Venezuela. See id. at 65 (citing Exec. Order No. 13857, 84 Fed. Reg. 509 (Jan. 25, 2019)); id. at 103-04 (same). Crucially, that order broadened the definition of "Government of Venezuela" to include several new entities, such that those entities were then also subject to the sanctions imposed on the Maduro regime.

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