I'm not going to comment on the taxi regulation system in SF because its pretty ugly. But the drivers have to drive for about 15-20 years to win a medallion. SF is changing this process and wants to start selling medallions for about $250,000. If you're at the top of the list (ie you've been waiting 15 years) you get first chance at buying a medallion but you're SOL if you don't have the 12K deposit.

If I were someone near the top of the list but hadn't been saving up I'd be pretty pissed too.