Think the guy in question does have a case from what I have been reading, he registered his domain in 2000 and I-Tunes didn't launch till 2004 during all which time he used the site redirect traffic to a music search engine. It's not as though he bought the domain, didn't use it and then tried to sell it to Apple after it had sat dormant for 4 years.
From El Reg
Quote:
Cohen, the 22-year old founder of SoJewish.com, registered the address in November 2000 after he was unable to register tunes.co.uk. Apple did not launch its iTunes service in the US until April 2003. Apple's lawyers got in touch and offered him $5,000 but Cohen was holding out for £50,000 . He uses the site to redirect traffic to one of his properties - quickquid.com.
Apple's lawyers stopped talking when Cohen made clear how much cash he wanted, according to the Guardian newspaper. Cohen is asking the High Court for a judicial review because he believes Nominet's procedures are biased in favour of big companies at the expense of smaller competitors
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I think the bit in red is what is causing the problem and why he was forced to hand it over to Apple.
More info
Here
To be honest though I don't have a lot of sympathy for him since he was only using it as a redirect and wasn't hosting a full blown site on it.