Looks like the time is nigh for Clear Channel iHeartMedia to pay the piper.

Those who hold a significant portion of iHeart’s $20+ billion in debt are balking at the company’s attempt to kick the can down the road. This spring, iHeart floated proposals to creditors to extend the time the company gets to pay back on its debt while pegging a higher interest rate and some equity to the revised payback-plan. The offers were roundly rejected – fewer than 1% of existing note-holders accepted the terms, and now the company’s repeatedly extending the deadline to creditors hoping they will accept it.

This is unlikely given the fact that a group of creditors have forged a “cooperation agreement” to actively resist any further debt restructuring along the lines of the company’s current proposals. According to Reuters, these creditors “represent more than half of the term loans holders” and one analyst believes iHeart brought it on itself by being overly aggressive with its restructuring plans; this “may have resulted in some hurt feelings and emotions that may be further complicating this.” Some creditors have also expressed no confidence in those working on an iHeart restructuring plan.

In April, iHeartMedia also disclosed that its solvency over the rest of the year is now an open question, and Wall Street analysts bluntly raise the notion of Chapter 11 when assessing the company and alluding to shareholders being “wiped out” when that happens.

Signaling that not much has changed in the legacy-mentality of iHeart when it comes to radio, the company’s been busy cutting staff at its radio stations, ostensibly in hopes of sweetening its account balances in preparation for bankruptcy negotiations. It’s tantamount to someone near death defaulting to the Middle Ages-style “medicinal” practice of bloodletting, which at this juncture makes the indebted assets themselves less valuable.

The game of fiscal chicken is now on in earnest. iHeartMedia is betting that many of its creditors will accept a fraction of what they are owed rather than get nothing at all if the company commences bankruptcy proceedings. It’s already welshed on one debt-payment, and iHeart’s PR team has already pivoted from going after negative corporate coverage to no-comment mode. This is what going for broke looks like.

I’m mostly curious about what a post-bankruptcy iHeartMedia will entail. Massive liquidation is highly unlikely, given that the company has about $7 billion more in debt than all of its assets are actually worth. For all its hype about being a 21st century media company, its prime source of revenue is in its outdoor billboard advertising business; the foray into radio has been great for pillaging the stock and bond markets for two decades, but that gravy train has dried up. Who blinks first: the company or its creditors, and how does the bankruptcy itself play out?