Carl C. Icahn, the billionaire investor who was a close confidant of President Trump, has received a second subpoena from federal prosecutors in Manhattan, this one related to a series of stock trades last year.
Icahn Enterprises, one of Mr. Icahn’s main investment companies, disclosed in a regulatory filing on Thursday that it had received a subpoena in June seeking “production of information pertaining to trading in shares of Manitowoc,” a crane manufacturing company.
Icahn Enterprises said it had complied with the request, but it was unclear why the company was disclosing the subpoena only now. There was no mention of it in the 2018 annual report that Icahn Enterprises filed in early March.
The filing did not disclose details of the trades that prosecutors were interested in, but a timely sale of Manitowoc shares in early 2018 prompted questions from the news media. Mr. Icahn, who had previously served as an unpaid adviser to the Trump administration, sold $30 million worth of Manitowoc stock in early 2018, not long before the White House said it was imposing tariffs on foreign-made steel.
The tariff announcement took a big bite out of the stock price of companies that are dependent on steel, such as Manitowoc.
Mr. Icahn remains one of the company’s largest shareholders. After the details of the stock sale were reported, Mr. Icahn denied having advance knowledge of the steel tariffs.
Reuters first reported the disclosure of the subpoena. Mr. Icahn did not return a call seeking comment on Friday.
The subpoena is the second formal demand for documents that Mr. Icahn, an early supporter of Mr. Trump’s run for the White House, has received from federal prosecutors in the past two years.
The first subpoena was issued in September 2017 and sought information about his activities as a special regulatory adviser to the Trump administration on policies for ethanol and other renewable fuels. Mr. Icahn quit the unpaid position in August 2017.
Mr. Icahn’s role as special adviser raised ethical concerns because of the influence he could potentially wield over the Environmental Protection Agency and its renewable fuels standard program. At the time, an oil refinery company that Mr. Icahn controls, CVR Energy, stood to benefit from a policy change he was recommending that concerned the way corn-based ethanol is mixed.
As a special adviser, Mr. Icahn helped interview Scott Pruitt, who would become the E.P.A. administrator.
In Thursday’s regulatory filing, Icahn Enterprises said the United States attorney’s office for the Southern District of New York “has not made any claims or allegations against us or Mr. Icahn with respect to either of the foregoing inquiries.”
Mr. Icahn, 83, who is reported to be worth more than $18 billion, is no stranger to controversy. He was one of the first so-called corporate raiders and helped fashion activist investing as a mainstream strategy for hedge funds. His aggressive approach in seeking corporate changes from the management of companies he invests in has won him both fans and critics over the years.
Mr. Icahn’s name also surfaced in an insider trading case two years ago, although he was not charged. One of the brokers who testified in the trial of William T. Walters, who had been one of the most successful sports gamblers in Las Vegas, said some of the former gambler’s trading ideas had come from Mr. Icahn.
Mr. Walters was convicted of insider trading in April 2017 and sentenced to five years in prison for his role in a $43 million scheme.
