This is an especially poignant story, and it's hard to not feel bad for this driver. On the other hand, people face investment risk all the time, i.e. when franchising a restaurant. When Chipotle or whoever comes in and devours the fast food market, I wonder if the local struggling burger franchisee asks the city for help? I can't speak on behalf of other cities, but anyone who has lived in SF pre-Uber has no shortag…
People face investment risk all the time, but medallions are a case of a city setting explicit expectations when selling the medallions and then changing the terms of the deal post facto. Chipotle devoured a huge chunk of the fast food market, but the city didn't collect money from McDonalds for a guarantee that Chipotle wouldn't be allowed to enter. Notably, this is illegal by federal law for auto manufacturers and…
You can't make a contract with a legislature. Exchanging anything of value for changes to the law is literally illegal. Imagine what would happen if you could bribe Congress to pass some corrupt legislation granting you untold powers and the next Congress was prohibited from undoing it. The only thing that binds Congress is the constitution.
Obviously that leaves you in a tough spot if you have to rely on the state of the law, but legislatures know that. If they make huge unexpected changes to the law it tends to have a negative effect on the markets, so they try to avoid doing that, and people then rely on them trying to avoid doing that. But sometimes they have to, or sometimes they do it when they don't have to, and you take your lumps (or vote the bums out).