This is such an upsetting characterization of the situation.
The city government sold a bunch of medallions to investors/"speculators" (depending on your politics). Those medallions declined in value. Who should bear that loss?
The entire situation was created by a government monopoly that never needed to exist in the first place. Now that someone's figured out how to go around it, all the investors in the manufactured, useless regulation are losing their shirts.
It's really hard to feel bad for these guys. They were willing participants in a system designed to line their pockets by fleecing ordinary people, choking supply to ensure their prices were kept artificially high. They're basically the OPEC of transportation. Do we feel bad because electric cars are disrupting OPEC?
Lyft and Uber really aren't the bad guys here, at all.