Both of the examples you've used are contracts that regularly get trounced on in courts. Just because something is written in a contract doesn't make it legally binding. Crazy at it sounds, and as much as it pains me to type it, it's the truth. A sporting complex can state in their contract that they are not responsible any personal injuries during your stay at their complex, but if a hand rail breaks and you fall down the steps, you can still sue them.
I know this will shock some, but it's the truth. I've seen enough busted contracts in my day to know...
I think you're conflating the issue by confusing what it means for a contract to be legally binding... Allow me to explain...
Using the sporting complex example...
1. The contract you enter into is enforceable and binding provided that both parties knowingly entered into the contract... Whether you read the contract or not, "knowingly" means that they knowingly provided you a service for which you knowingly paid them consideration (e.g. money), both equal to the service and consideration agreed to in writing.
2. Contracts that are unenforceable by design are pretty limited. These include gambling bets and contracts interrupting or interfering with the binding marriage of one person to another, and/or contracts in which the service required is blatantly illegal... Agreeing to waive certain rights is not necessarily illegal unless it is stipulated expressly in statutory law that it is. A contract is not implicitly illegal simply because it involves rights being waived. This includes waivers of liability, and waivers of rights enumerated in the Constitution UNLESS the other party to the contract is a governmental body because Constitutional rights enjoin only Congress, the government, and agencies/departments of the government.
The mistake you're making is confusing the enforceability of a binding contract in principle with the initiation and outcome of litigation aimed at interpreting enforceability as well as the relevant sections of law.
Back to the sporting complex... If you agree to waive liability rights upon entry to a sporting complex, there's nothing illegal about it. Whether or not you can sue them has nothing to do with whether a waiver of rights is criminal or not. Disputes between two parties are torts.... this case is tort law, not criminal law. The fact that you can file suit to dispute the interpretation and enforceability of waiver doesn't guarantee that you will win, nor does it guarantee that the court will not bind you to other provisions of the contract that are themselves wholly enforceable.
The enforceability of a waiver clause also depends on where the negligence lay...
I'll give you two examples with separate potential outcomes:
1. Guy is leaning over a railing and falls and breaks his wrist. This guy will most likely be unsuccessful in bringing suit against the complex because he waived his rights and the accident was due ostensibly to his own negligence... Even worse if warning signs advise patrons to not lean on the railings (which they usually do). This example is the reason why sports complexes include such a clause.
2. Guy is walking up stairs that are icy, have not been cleaned by the complex proprietors, and have no warning signs indicating ice on the stairs. The guy falls and breaks his leg. This guy COULD win because despite the liability waiver, the negligence here is the stadium's. They failed to properly maintain the stairs, to properly block off or to warn the patrons of the risk.
3. Guy is pushed down the stairs by a staff member forcibly and breaks his leg. Guy wasn't doing anything wrong and the staff member was being a jerk. Not only could he sue the stadium but also the individual who pushed him. He could sue the stadium for negligence and the individual for assault and battery, and there could be criminal charges brought against the individual for assault and battery. The waiver of liability may not apply here because there was negligence by stadium staff AND a criminal act involved.
Note that in all three of these examples there may be no statutory law that sets in stone what the outcome will be. In these scenarios it's up to a judge and/or jury to determine the outcome based on their interpretation of a combination of statutory law as well as case law (precedent decisions), and the underlying protections implied by both.
Since tort lawsuits can end up costing a lot of money, as lawyers don't work for free, it is always best to try to resolve such disputes directly. The guy ultimately wants his iPhone serviced... but the store is potentially misinterpreting the contract. This may just be an honest mistake by the store. Stores get things wrong sometimes... they're not manned by legal experts making $300 an hour. But a quick discussion with the right people could lead to a happy outcome for all. If the guy knows he is well within his rights to get service, he should explain his reasons for believing so to someone who is in a position to authorize that the service be done.
If after escalation it goes nowhere, one has to weigh how much the issue is costing them against how much fighting the issue will cost them. Ultimately, in a class action lawsuit the lawyers on both sides are the ones who make the bulk of the cash and the little guy may make out with nothing... even possibly be in a bigger hole.
