While I appreciate your insight, and I am sorry to go off topic (as this was meant to be, for Cincinnati) but I am quite certain that Cumulus and iHeartRadio will always risk some form of bankruptcy; due to the points that I mentioned above. The only alternative for them would be to simply sell off a few stations. But that would be playing into another Radio competitors' (i.e. Entercom, Townsquare) strong hand.
The issue is that the stations, sold separately, are worth less than the total debt. A lot less. So selling a few stations at far less than were paid for them does not pay down the debt much, and reduces the ongoing cash flow that could be used to pay the remaining debt.
Example: in 2000, the 5 LA FMs were worth, in total, about $1.6 to 1.7 billion if we used what Radio One paid in that era for its single station ($400 million). Today, even with the large cash flow, they are likely worth perhaps $500 to $600 million at best... so it's not worth selling them in pieces.
Personally, I cannot understand how Cumulus and iHeartMedia have avoided Bankruptcy for so long.
They are both profitable on an operating business. The groups of radio stations make money.
They don't make enough money to pay the loans, though. They have managed to "kick the can" down the road by a combination of asset sales (like the towers, owned property sold and leased back, etc.) and refinancing. However, all they have done is postpone the payment of debts that are coming due eventually.
But one explanation is that they are being illegally funded by corporations or our own (Federal government?). These two corporations should be seeing the same things that Citadel was becoming before it eventually folded. I struggle to make sense of how they are doing it, and am wondering if there is a secret scandal going on that is keeping both companies on welfare.
It's normal business. Kind of like using one credit card to pay off another. Eventually, there is a time when the house of cards collapses or the lenders do a debt restructuring.
The government has nothing to do with this. And the only "corporations" involved are the lenders and investment bankers who bankrolled the original purchases. This is like the mobster who will break the kneecaps of someone who is behind on his vig, but who will not kill the debtor as dead men don't pay their debts.
So the lenders want both of those groups alive, because they think that they can at least get some of the money back. And "some" is better than "none". Bankruptcy generally results in none or little of the money being paid.