Levoff, who until last year was Apple’s senior director of corporate law, traded on advance knowledge of revenue-and-earnings figures multiple times dating back to 2011, the Securities and Exchange Commission and federal prosecutors said Wednesday. The illegal investments led to about $227,000 in profits while allowing him to avoid $377,000 of losses, according to the U.S. attorney’s office in Newark, New Jersey, which filed criminal charges against Levoff.

For instance, in July 2015, Levoff learned that Apple wouldn’t meet analysts’ third-quarter forecast for iPhone sales, the SEC said in a related civil complaint. That month, he sold about $10 million of Apple stock — virtually all of his holdings — to avoid losing about $345,000, the SEC said.

Levoff and an attorney representing didn’t immediately respond to a request for comment.

Levoff was fired in September 2018 after being placed on leave last year, according to the SEC’s filing. Over his decade long career at Apple, he was one of the company’s most senior executives, reporting directly to the company’s general counsel.

In his role, Levoff was in charge of Apple’s insider-trading policy and was its named representative on many of its subsidiaries and corporate acquisitions. Levoff was deeply familiar with the company’s trading policies, routinely sending emails to workers reminding them not to buy and sell stock amid earnings announcements, the SEC said.

The SEC is seeking monetary penalties and a prohibition on Levoff, 45, serving as an officer or director of a public company.

The allegations are a black eye for Apple, which has mostly had a clean record over financial reporting issues since its co-founder and former Chief Executive Officer Steve Jobs was accused of options backdating by shareholders in the mid-2000s.