I hope this comment does not get me down voted into oblivion, but just to play the devils advocate here, the guy did sign the non-compete agreement, which, setting aside legal aspects, is kind of like giving your word. I agree, non-compete agreements are stupid, but you don't have to sign them, you can always take a different job that does not require one, probably for less money. What is your word worth?
I'm not a fan of down-votes, but I will try to (kind of) refute your central point according to the argument pyramid. (Not fully disagreeing with you, just some thoughts on the matter).
The central question is: did he really knowingly sign a non-compete agreement and is it lawful in the jurisdiction?
Yes, he signed the contract, which was likely a 20 page standard issue paper that was mostly written by Amazon lawyers in small print.
Now most of us don't send a copy of employment contracts to our layers and discuss it with them for hours before signing (that's kind of expensive).
That's why there are some limitations on what can go into a contract in some places (at least in Europe, but I assume the U.S. has something similar). For instance they can't write in there that you will be their slave, providing unpaid work without the ability to quit, be beaten as motivation and lawfully enforce it, even if you sign the paper.
Other things need to be explicitly clarified to be accepted at court. For instance, if a big software corporation would add a clause to their license agreement on page 25 that your house belongs to them if you click on "I Agree", it would most likely not hold ground in a court. If they explicitly explained this to you (with a few witnesses), it might be heard in court.
The question here is (and it's far from clear cut) is if this contract holds it's ground in court.
Back to the central point: this means, that Amazon might have to prove that they made a good effort to clarify this clause in the contract explicitly and it's lawful in the state he worked. That's up to the court to decide.
Now if they can prove that they did make a good faith effort to clarify his contract, he agreed and then went on and willfully broke it, then he is in a troublesome spot.
INAL, this is not an advice for anything and I'm not liable for any of the above.
Good point. I did not think of that, legal agreements can be made to obfuscate, much like those online agreements. If that is the case then I am with you completely, it is unfair. But if he signed it knowing the consequences then he should live them in my view.
"But if he signed it knowing the consequences then he should live them in my view."
Why? It is not immoral to break a contract. It happens all the time in good faith. The "wronged" party is only entitled to provable damages. Which as long as he isn't running away with trade secrets, or cold calling his old clients, then what provable damages are there?
Contracts are a civil matter. It is immoral to write a "punishment" clause into a contract and nobody should have to "live with them".
