Will NY's courts automatically hold a 'key employee' to a non-compete agreement?

The short answer is no, they won't. While there are certainly some circumstances where New York's courts will be more likely to uphold a non-compete clause against a key employee than against a standard employee, the standard applied is still a daunting one. For additional information on this standard that the employer must satisfy under New York law before a key employee will be restrained from competing with his former employer, please see "When NY Courts Won't Enforce a Key Employee's Non-Compete Agreement."