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.

And Ukrainian officials, with national survival at stake, welcomed back local arms dealers whom, before the war with Russia, they had worked hard to sideline. Early in the war, which began in February 2022, officials scrapped many public procurement and transparency rules and invited private brokers to compete with government buyers. Now, after the firing of the defense minister, Oleksii Reznikov, Ukrainian officials are publicly questioning this weapons-at-any-cost strategy.

Mr. Morales declined to be interviewed. Bryan Van Brunt, the general counsel for Mr. Morales’s company, Global Ordnance, said the company followed the law. “Contrary to what we may see in the movies, long-term success depends upon knowing, fully respecting, and following the rules of all countries involved,” he wrote in an email.

Sergeant Koyfman, a Ukrainian American with years of experience as an adviser to Ukraine’s national guard, enlisted when Russia invaded, documents reviewed by The New York Times show. His exact military duties are unclear. He told The Times that he is a chief sergeant in the Ukrainian territorial defense forces, where he supervises and trains a cadre of soldiers. “We are fighters,” he said.

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