Prosecutors claim Lewis orchestrated a “brazen” insider trading scheme by passing information about companies to friends, pilots, and a former girlfriend.

A majority of the Tottenham Hotspur soccer team is owned by Lewis’ family trust. He entered his plea before U.S. Magistrate Valerie Figueredo in Manhattan.

Lewis will be released on $300 million bond secured by his yacht and private aircraft, according to prosecutor Nicolas Roos.

Patrick O’Connor and Bryan Waugh, two of Lewis’ pilots, pleaded not guilty to insider trading charges after being accused of illegally profiting from Lewis’ tips. Each of their bails was set at $250,000.

Forbes magazine estimates Lewis is worth $6.1 billion after founding the investment firm Tavistock Group. At the arraignment, he wore a gray suit without handcuffs.

He was voluntarily brought to the United States to defend himself against charges, his lawyer said, saying that prosecutors committed an “egregious error.”

O’Connor’s and Waugh’s lawyers declined to comment after the hearing.

As a result, Tottenham has no comment on this legal matter, a spokesperson said.

According to prosecutors, Lewis lent each pilot $500,000 and encouraged them to buy stock in oncology company Mirati Therapeutics before it released favorable clinical data.

“The Boss has inside information,” O’Connor texted a friend, according to the indictment.

The share price of Mirati increased 16.7% in one day after Mirati announced the positive results, and both pilots repaid Lewis’s loans.

Lewis was notified that the repayment was a “loan payback for MRTX.”

A comment from Mirati was not immediately available.

For alleged crimes from 2013 to 2021, Lewis faces 16 counts of securities fraud and three counts of conspiracy. He could theoretically spend decades behind bars.

According to prosecutors, Lewis held board seats at several companies and deputized employees to serve on boards, giving him access to inside information.

There was no need for all of this,” Damian Williams, the U.S. lawyer in Manhattan, said. “Joe Lewis is wealthy.”

Under his predecessor, Preet Bharara, Williams’ office began cracking down on insider trading in 2009.

Both O’Connor and Waugh, who live in New York and Virginia, are charged with securities fraud and conspiracy.