I'd be awfully surprised if any of those watches had a retail price of over $500. Even if they were gifts, I think that they would be non-luxury brands with a luxury look. The GB isn't that stupid that they would open themselves up to criticism by wearing some luxury brand as well known as Rolex (or similar).
What is hysterical to me, is that as much as the WTS loves to bash educated, white collar executive jobs, many of them clearly yearn to project that image to the outside world (and to boost their own egos). Instead of wearing a $10,000 Rolex or $3,000 custom suit, they wear flashy Michael Kors watch they got on sale for $109 and the Chaps by Ralph Lauren suit they got on sale for $199, both at Marshalls/T.J. Maxx/Kohls.
Even their pocket handkerchiefs betray them. Roam the halls and conference rooms of any Fortune 500 company, and you'll see some nice linen pocket squares or the occasional Hermes silk pocket square-- not some 1990s Men's Wearhouse version like most of the GB wear.