This Herbert Kliegerman is no genius.
Firstly, Apple announced the exclusive deal with AT&T in January when they announced the iPhone.
Secondly, he had near 7 months to read the press releases, terms, news, Apple website for info on his upcoming purchases and the contractual limitations therein.
Thirdly, Apple should take his phones away from him as he is clearly not a deep thinker.

I wonder if he thought about his phone bill when he was using it in Mexico!! How many minutes did he use. He makes it seem like he just used a couple minutes and now he has a 2000.00 phone bill.
Whatever.

An idiot is born every day. Anyone who thinks that ANY agreement in the US is somehow going to be valid when you visit ANOTHER COUNTRY, especially a mobile phone contract, deserves a $2000 bill. Americans should have to take a common sense test before being allowed to travel abroad.

I hope they send him to collection and ruin his credit for being a fool.

Other than a small fraction of general population that closely follows tech, and that heard all the hype about Apple, nobody really knows or cares what is in some contract.

For years (close to a decade), GSM mobile providers were allowing their customers to unlock their phones and use SIM cards from other carriers. This is still common practice with every cellphone out there (GSM, of course). It is therefore quite reasonable to expect to be able to unlock your phone if it is GSM. Again, people that closely follow tech probably expected that Apple and AT&T will have some unique deal regarding iPhone, and unlocking would, at least at first, be out of the question. Normal consumers, however, would have no way of expecting this, since years of prior experience with GMS phones tells them otherwise. So when AT&T says: "No unlocking!", then tells user, "just have global roaming turned on", ordinary user can easily assume: "Oh, OK; I can't use local SIM, but they obviously have some special arrangement here, so my global roaming won't be exorbitant as with other phones". This makes total sense to normal, mainstream people.

Depending on the skill of the lawyer, this guy my have a case. Mind you, he isn't asking for his money back; he's asking for the ability to unlock, and for better disclosure.

Lets just say that Predrag is correct in assuming that the normal consumer is not up on the news, tech news, reading terms and conditions or basic contract law.
Why did he buy not one or two but three iPhones if he was so woefully ignorant of the terms of the contract he was signing.
By the way, it could be argued that anyone buying three of the five or six hundred dollar phones of a type never before offered and that are touted as being revolutionary and groundbreaking is probably not a "normal" consumer.

How difficult would it be to put a widget on the iPhone that summarizes account status at any given moment?

Customers who file suit dredging things up? This guy is an example of a whole new species of leech, drawing blood from the rest of us. Not every customer does this.