The funny thing is, when you see "Divas" and sports stars wearing expensive watches, they usually didn't pay for them. They're either on loan from the watch company or a gift in exchange for the promotion value of having a celebrity wear their watches. John Travolta is on the Breitling payroll, Nicole Kidman and George Clooney shill for Omega. Charlize Theron got the boot from Raymond Weil and was hit with lawsuit for breach of contract when she was spotted wearing another brand publicly. They had paid her $3 million to wear nothing else.
Since the watches are insured by the promoter, they really don't care if it's stolen or damaged - they just get a new one from the company. Even if it's a $50,000+ watch.