An arms dealer finds a fortune from Ukrainian military ties and Pentagon cash.

Ukrainian officials gathered over afternoon drinks last month at the penthouse bar of the 11 Mirrors, one of Kyiv’s swankiest hotels. They found their host, a Florida arms dealer named Marc Morales, telling stories of his fortune; his new $10 million yacht, the Trigger Happy; and his search for a manager for his company’s nine-digit portfolio.

In the 18 months since Russia’s invasion began, Mr. Morales has become one of Ukraine’s most important weapons suppliers. The Pentagon has awarded his company about $1 billion in contracts to buy ammunition from around the world. And records show he has built a roughly $200 million side business selling to the Ukrainians directly.

Mr. Morales has done so while employing a chief sergeant in the Ukrainian military who sets up meetings with government officials — an unusual arrangement that legal experts say tests the boundaries of both American and Ukrainian corruption laws prohibiting payments to government officials. He has also hired away a longtime adviser to Ukraine’s defense minister, who was fired recently amid concerns over graft and mismanagement. And Mr. Morales’s company has been under investigation by Ukrainian anticorruption authorities over a deal that government officials said was botched.

In that way, the deals with Mr. Morales are reminiscent of Ukraine’s freewheeling past, when arms dealers forged cozy relationships with military officials, contracts were signed in secret and weapons brokers frequently found themselves under investigation. The United States has lectured Ukraine’s leaders for more than a decade about the need to clean up that system.

Mr. Morales, 51, was an unlikely choice as one of the Pentagon’s go-to arms dealers.

The Justice Department indicted him in 2009 on conspiracy and money laundering charges after it said he was caught on tape discussing methods for paying bribes to foreign officials. “You just got to be smarter than the government,” Mr. Morales said on one recording. (F.B.I. agents badly botched the case, and prosecutors ultimately dropped the charges.)

But the war changed the calculus for the Ukrainians and Americans alike. The Biden administration, seeking to arm Ukraine but reluctant to commit troops, needs people like Mr. Morales, who proved in Afghanistan and Syria that he could consistently acquire and deliver weapons.

Natalia Yermak, Daria Mitiuk, John Ismay and Tomas Dapkus contributed reporting.

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