In one of the stiffest penalties ever imposed on individual defendants in a securities fraud case, a judge has ordered billionaire Sam Wyly and the estate of his late brother Charles Wyly to hand over at least $300 million to the U.S. Securities and Exchange Commission.

In an 83-page ruling issued on Thursday, U.S. District Judge Shira Scheindlin in Manhattan ordered the Wylys to disgorge 25 percent of their total profits from a secret scheme to hide trades in public companies they helped direct. Scheindlin also ordered disgorgement of taxes the Wylys avoided paying through the scheme. Excluding prejudgment interest, the judge put Sam Wyly on the hook for $123.8 million and Charles Wyly for $63.8 million.

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