Court jails advisor for flouting SEC ban and running firm

A financial advisor who ignored a federal ban and kept running a firm anyway just lost his appeal—and the court isn’t letting him off easy. 

On November 18, 2025, the First Circuit Court of Appeals upheld a twenty-month prison sentence for Craig Medoff, a name that’s become familiar in regulatory circles for all the wrong reasons. Medoff’s story is a cautionary tale for anyone in the investment business who thinks they can outmaneuver the SEC or brush off a court order. 

Let’s rewind to 2016. After years of trouble with the Securities and Exchange Commission, Medoff agreed to a court order that was supposed to sideline him from the securities industry for a decade. The order was clear: no more issuing, offering, or selling securities – directly or through any company he controlled. He was also hit with a $100,000 penalty and told to pay back profits from earlier misconduct. But Medoff didn’t pay up, and he didn’t stay out of the business. 

Instead, he quietly took the reins at Nova Capital International LLC, a financial services firm, and kept collecting fees – about $1.8 million worth – while using an alias to cover his tracks. The SEC eventually caught wind and brought the matter back to court. This time, the judge decided that civil penalties weren’t enough. With Medoff’s track record of ignoring orders, the court turned up the heat and charged him with criminal contempt. 

Medoff pleaded guilty in 2024. At sentencing, the judge looked at the whole picture: not just this latest violation, but a pattern stretching back to the 1990s. Medoff had a history of running afoul of securities laws, failing to pay fines, and generally refusing to play by the rules. The court decided that the usual four-to-ten-month prison range wasn’t going to cut it and doubled the top end, sending Medoff away for twenty months and adding a $20,000 fine. 

Medoff tried to argue that the judge was biased and that his sentence was too harsh, but the appeals court didn’t buy it. The First Circuit said the judge was right to take Medoff’s long history into account and to send a message that court orders matter. 

For those of us in the investment world, the lesson is simple. If you get banned, you’re expected to stay out. If you don’t, the consequences are real – and the courts are watching. This isn’t just about one advisor’s downfall; it’s a reminder that compliance isn’t optional, and regulators have the tools – and the will – to enforce the rules.