To be clear about exactly what happened.
In 2007~2008 the CTA was having financial difficulties. The Illinois legislature made a deal to bailout the CTA from some financial difficulties.
At the last minute Governor Blago, who is now in jail for trying to sell a Senate set, thew in an additional condition: free rides on all Il public transportation for handicapped and seniors.
It really pissed the legislature off because they had to redo the whole budget, but it got passed. He looked like a hero to seniors and the handicapped.
Eventually he got inmpeached and the new Gov discovered that free rides were not sustainable. So they means tested it.
Keep in mind though, that a largbe part of the cost is due to pensions for Chicago machine "cronies".