A big boy letter is a private agreement between sophisticated parties for sale of publicly traded stocks with a negative covenant not to sue or litigate over withholding of material inside information in such transaction. By subscribing to such agreement the buyer virtually recognizes that the seller is better equipped with vital information but promises not to sue the seller. This understanding seeks to protect disparate information position of the parties.
The validity of big boy letter is a vexed and debatable issue in law. Judicial opinion is divided on the practice of big boy letter. Such situation has raised not only security law issues but also common law fraud issues. Under the provisions of Section 29 (a) of the Securities Exchange Act of 1934 waiver of liability for securities fraud is void. While some courts have upheld agreements similar to big boy letter against the buyer, others have struck down such agreements, relying on the aforesaid anti waiver provisions of the Securities Exchange Act.
Insiders are prohibited from trading in securities on vital information that they have been privileged to receive in confidence, to their undue advantage over other investors. For instance, insiders with information advantage might persuade others to sell stocks of the company at a throw away price to them or their nominees when the company is on the verge of reporting high profits and declaring good dividends. Significant challenge to big boy letter arrangement is on the ground that the same constitutes insider trading, which is banned. Rather illegal insider trading, punishable with insider trading penalty, is encouraged in the practice of big boy letter.
The perception is growing that any body in possession of valuable non public information has an absolute duty to disclose the same or otherwise refrain from trading in such securities altogether.