Long story short: Yesterday Gawker issued a bounty on information on the Apple tablet. Today, Apple famously heavy handed lawyers issued a cease and desist (and send us anything you get) order.
The legality question is: Is anything that Gawker gets a violation of contract theft of Apple's trade secrets? Certainly most of what they are asking for would seem that way.
Their $50,000 prize is for a picture of Steve Jobs with a tablet. If you were at a restaurant and the guy next to you was Steve Jobs and he was showing off the tablet to Al Gore, and you snapped a picture, would it be against the law to sell it?
In any case, Gawker is getting what they wanted in the first place with this contest: