>Sad story but every economic change for the better creates winners and losers. You can't regulate away loss without regulating away improvement.
The government isn't a third party here. Compensating him isn't just handing him money for a bad investment. It's compensating him for the fact that SF scammed him out of a quarter million dollars.
The reason why the government should have to compensate here isn't because he lost money and pour him. It's because the government sold him a license and then devalued the license on purpose.
You could argue that the city never promised to prevent all sorts of transportation competition. And he took that risk knowing that, for example, people could take limos or whatever. But you at least have to have that debate. You can't just write it off as a bad investment. The government is the cause of his loss. Not the market.
>As for the government stepping in - live by the fake government market, die by the fake government market. I have no sympathy for people who build businesses behind government firewalls or with government subsidies, and suffer when those rules change.
You act like cabs were regulated for the cab drivers benefit, but that's not how or why they were regulated. They were regulated for the benefit of the city and the rides. The medallion system was the other side of a compromise between the city and the taxis. The city would regulate pricing and dictate key parts of their business model, but in exchange they would be protected from competition. It was a quid pro quo.
IF you think the medallions shouldn't have been sold in the first replace, why isn't just returning them for the price paid the best solution?