Robert Chestman, a stockbroker, first met Keith Loeb in 1982 when Loeb sought to consolidate his and his wife Susan's holdings in Waldbaum, Inc., a publicly traded supermarket chain. During their initial meeting, Loeb told Chestman that his wife was a granddaughter of Julia Waldbaum, a member of the board of directors of Waldbaum and the wife of its founder. Julia Waldbaum also was the mother of Ira Waldbaum, the president and controlling shareholder of Waldbaum. Over the next four years, Chestman executed several transactions involving Waldbaum stock for Keith Loeb, and Loeb sent Chestman a copy of his wife's birth certificate indicating that his wife's mother was Shirley Waldbaum Witkin.
On November 21, 1986, Ira Waldbaum agreed to sell Waldbaum to the Great Atlantic and Pacific Tea Company at $50 per share for a controlling block. Two days later, Ira told three of his children, his sister Shirley Witkin, and his nephew Robert Karin about the pending sale, admonishing them to keep the news confidential and offering to tender their shares along with his to simplify the process.
Despite the caution, Shirley told her daughter Susan Loeb on November 24 that Ira was selling the company, warning her not to tell anyone except her husband Keith because disclosure could ruin the sale. The next day, Susan told Keith about the pending tender offer and cautioned him similarly.
On November 26, Keith telephoned Chestman at 8:59 a.m., leaving a message to call ASAP, and later between 9:00 and 10:30 a.m. told him he had some definite, accurate information that Waldbaum was about to be sold at a substantially higher price. Chestman responded that he could not advise Loeb what to do in a situation like this. Later that morning, Chestman purchased 3,000 shares for his own account at $24.65 per share and between 11:31 a.m. and 12:35 p.m. purchased an additional 8,000 shares for his clients' discretionary accounts, including 1,000 shares for the Loeb account. After another call, Chestman indicated Waldbaum was a buy, and Loeb ordered 1,000 shares.
The tender offer was publicly announced after the market closed, and the stock rose to $49 the next business day. In December 1986 and April 1987, after learning of investigations, Loeb contacted Chestman, who claimed the purchases were based on research. Loeb agreed to cooperate with the government, disgorging profits and paying a fine. A grand jury indicted Chestman on July 20, 1988, on thirty-one counts. The district court denied Chestman's motion to dismiss the indictment. After a jury trial, he was convicted on all counts. A panel of the Second Circuit reversed the convictions, but the court granted rehearing en banc on the Rule 14e-3(a), Rule 10b-5, and mail fraud convictions.
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