The parent company of iHeartCommunications, which syndicates programs by conservative talk-show hosts Rush Limbaugh and Sean Hannity, appears to be headed toward bankruptcy.

In a statement filed last week with the Securities and Exchange Commission, the federal agency charged with regulating companies that offer investments to the public, iHeartCommunications’ parent company, iHeartMedia Inc., said that it had “substantial doubt” that it would be in business by the middle of next year.

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Formerly known as Clear Channel, iHeartCommunications also distributes the shows of entertainers Steve Harvey and Ryan Seacrest. It also owns and operates more than 800 radio stations.

The radio industry as a whole has been fading away, not because people aren’t tuning in but rather because advertisers have been shifting their dollars to the online world where performance can be measured much more effectively, according to radio industry veteran Seth Resler:

“What many people don't realize is that the job of a radio salesperson is getting harder as more and more clients start thinking about advertising as a science and not an art," Resler wrote. "As an industry, we simply aren't providing them with the tools they need to compete against these new mediums.”

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According to a 2016 Pew Research Center report, more than 90 percent of Americans said they have listened to radio via an online or broadcast form in a given week.

The ad challenge is made worse for iHeartCommunications since many of its stations feature a conservative talk format whose audience is literally dying off. According to industry figures, the age of a talk show listener is about 67. Further complicating things for the company has been that its top host, Limbaugh, has immersed himself in several controversies in recent years, such as the time he called a liberal activist a “slut” on the air.

Being in an expensive, dying and controversial industry isn’t good for stock prices, which is why in 2008, iHeartCommunications became a wholly owned subsidiary of iHeartMedia in a $24 billion stock buyout transaction initiated by Bain Capital, the investment firm for which past GOP presidential nominee Mitt Romney labored for many years.

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That buyout option saddled iHeartMedia with a huge amount of debt, almost $350 million of which is about to come due, according to MarketWatch reporter Ciara Linnane.

In December, ratings agency Moody’s said that iHeartMedia had a “negative” outlook, a sign that its already junk-level bond rating might be downgraded even further.

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According to Reuters, iHeartMedia is trying to kick the debt can further down the road by trying to pay off its maturing bonds by selling new ones while undergoing yet another corporate overhaul.

But this time, the company’s bondholders aren’t playing along. Per Reuters, a group that claims to represent more than half of the company's lenders are refusing to cooperate with the restructuring plan, meaning that there is a very real possibility that iHeartMedia may have to declare Chapter 11 bankruptcy in order to evade its creditors.

Should such a restructuring happen, there’s a very real chance that it could allow iHeartMedia to force Limbaugh, Hannity and its other top talents to renegotiate their contracts for a lower payment amount. Of course, that’s assuming that there would be any takers on what are likely to be bonds that would be sold at fire-sale prices.

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Will Rush Limbaugh need a government bailout?