From the article:

" Although critics question the legality of TRAPs, a legal analysis published last year found that courts generally uphold the agreements in challenges brought under anti-kickback provisions of the Fair Labor Standards Act, the law establishing a federal minimum wage. However, the author of the study, Loyola Marymount associate law professor Jonathan F. Harris, said another type of legal challenge might prove more successful: courts could refuse to enforce TRAP contract language under the so-called unconscionability doctrine, a legal principle that allows judges to void agreements containing unreasonable terms dictated by a party “with superior bargaining power.” In 2000, the study noted, a federal judge in Manhattan nullified one employment agreement in the financial services industry, ruling that the language of the contract “approaches indentured servitude.” "

Additionally, it does not cost tend of thousands of dollars to have a law firm draft demand letters for debt. Even if the debt is contestable, theoretically, it remains a huge problem and not something that can be ignored.

I've been in a similar situation before. Employers who put this sort of stuff in their contracts are like landlords who say "you have to repaint the place on your own dime after 10 years of living there". They think they are being cleaver.

These employers don't want to go to court, they don't want to collect the debt, they just like scary language.

My employer threatened me with similar language, so I shrugged my shoulders and said "ok?".

Never heard of it again. They won't spend $20 to buy pizza for their employees, you think they'll spend money on lawyers?

You’re rolling the dice there on corporate attitude. If they’ve got lawyers on their payroll already it will just be standard cost of business to sue yet another employee. Or just straight up vindictiveness.

You can't get blood from a stone, and there's no law that says you can't deliberately set up your finances to be maximally stone-like. IMO you should be doing this anyways so that the medical billing system can't decide to steal your life savings.

Pretty much. The older I get, the more I realize there are "rules" and then there is what people are actually willing to do.

Sure, why wouldn't they? They only need to make an example of one employee every now and then to deter the rest.

What example? How can they get any money out of someone that doesn't have anything? Eventually, the debt will go to collections and someone might get 10% of the money collected.