The 86-year-old businessman entered the plea in Manhattan federal court six months after he was charged in the case. He had been free on $300 million bail, with a yacht and private plane serving as collateral.

Lewis did not speak as he left court, and he was shielded from photographers by his aides, a lawyer and an umbrella.

U.S. Attorney Damian Williams said the plea deal includes the largest financial penalty for insider trading in a decade.

Broad Bay Limited, which Lewis owns, will pay more than $50 million in financial penalties, the prosecutor said in a release.

“Today’s guilty pleas once again confirm — as I said in announcing the charges against Joseph Lewis just six months ago — the law applies to everyone, no matter who you are or how much wealth you have,” Williams said.

He said Lewis abused inside information he gathered from corporate boardrooms to tip off his friends, employees and romantic interests.

Federal sentencing guidelines call for a prison sentence of between 18 and 24 months, though Lewis can seek less than that. His sentencing hearing is scheduled for March 28.

As part of the guilty plea, Lewis and Broad Bay Limited have agreed that Lewis and his companies will resign and surrender control over board seats and participation in board meetings for any corporation publicly traded in the United States. They also agreed to quit ownership of certain investments over the five-year period of probation and to cooperate with the U.S. government’s ongoing investigation and prosecution.

Lewis has a fortune that Forbes estimates at $6.1 billion and assets in real estate, biotechnology, energy, agriculture and more. He bought an interest in Tottenham Hotspur, one of England’s most storied soccer clubs, in 2001.

Under his ownership, the Premier League club built a state-of-the-art stadium at an estimated cost of more than $1 billion.

Today, a trust benefiting members of Lewis’ family is the majority owner of ENIC, the holding company that owns the team. Lewis himself is not a beneficiary of that trust and relinquished operational control of the club in October 2022, according to corporate filings.

Lewis’ Tavistock Group owns all or parts of over 200 companies worldwide, according to its website, and his art collection boasts works by Picasso, Matisse, Degas and more. His business connections include Tiger Woods, Ernie Els and Justin Timberlake, with whom he built a Bahamian oceanside resort that opened in 2010.

According to the indictment against him, Lewis’ investments in various companies gave him control of board seats, where he placed associates who let him know what they learned behind the scenes. Prosecutors said Lewis improperly shared confidential information between 2019 and 2021 to his chosen recipients and urged them to profit from the tips.

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Associated Press Writer Jennifer Peltz contributed to this report.