They make lots of money. Hundreds of millions of dollars. It's just not enough to pay off the debt.
They might have had a lot of sales but they didn’t make money. Financial Wealth is created when there is enough cash generated to pay All of the expenses including debt.
Lots of companies stopped at a couple hundred stations voluntarily. Companies like ABC and CBS chose not to over-expand. Where are they now? Why did they sell?
ABC’s radio stations were a “distraction” for The Mouse. Disney’s business is movies, TV / cable networks and theme parks. BTW I believe they did keep a couple of radio stations for ESPN radio. They basically sold the radio stations that were not large clusters in their markets (big disadvantage) at top dollar tax free to Citadel. Citadel could not execute because they: paid too much, thought they could cut staff to make a profit, thought they were better programmers / operators than ABC, got caught in an economic downturn, or combination of factors.
CBS is all about TV and networks. The radio stations were in strong clusters and generating positive cash, but were a distraction to some Wall Street folks. There are a lot of traders in the financial markets that like “pure play” businesses that have some volatility so the options players can gamble.*
IMHO: CBS, Disney, and any one that sold out to Entercom, Citadel, CC, or Cumulus walked away from radio with cash or stock that could (should) have been sold for cash. Cash allows you to move on to other opportunities.
If you are not a "radio" company, why stay in a business that is going thru "changes" when you can cash out.
* IMHO The largest Casino in the world is the stock market.