This program will explain the principles of the insider trading law under Section 10(b) of the Securities Exchange Act and describe why it has proven to be so difficult to apply consistently. In recent years, the underlying, conceptual problem in the law was highlighted when judges of the Second Circuit sharply disagreed with each other in two high profile cases. In U.S. v. Newman, a unanimous panel reversed the conviction after trial of two hedge fund portfolio managers, declaring that their alleged insider trading conduct was in fact not illegal. Just a few years later, in U.S. v. Martoma, a different panel of Second Circuit judges affirmed the conviction of another portfolio manager as it disagreed with the thrust of the Newman opinion. A dissenting judge in Martoma wrote a vigorous dissent accusing the majority of flatly contradicting Newman. This split remains unresolved. In a new Second Circuit opinion affirming the conviction of another trader, U.S. v. Blaszczak, the Court condoned a wholly separate avenue for insider trading prosecutions that the Government will likely pursue in the future to avoid the mess that Newman v. Martoma presents. This will likely not be the last word on this complex area of the law.