If the company files without a pre-negotiated restructuring plan in place, the bankruptcy could turn into a free-fall, with some of the biggest and most contentious specialists in distressed companies potentially tussling for years over about US$20 billion ($27.5b) of debt.
Billionaire John Malone's Liberty Media stepped in with a last-minute offer to senior creditors that would help salvage iHeart by injecting cash and financing a trip through bankruptcy, but analysts have said the bid isn't high enough to win over creditors.
Still, talks remain fluid and ongoing between the secured creditor group and Liberty Media, according to the people.
Liberty has already bought a substantial position in iHeart debt and sees potential synergies between iHeart and SiriusXM radio, Chief Executive Officer Greg Maffei said Thursday on a call with investors.
IHeart runs the biggest land-based radio network with about 850 stations and Sirius has the largest satellite radio network.
Wendy Goldberg, a spokeswoman for San Antonio, Texas-based iHeart, declined to comment.
IHeart is controlled by Bain Capital and Thomas H. Lee Partners, which staged a leveraged buyout in 2008. The senior creditor group is advised by investment bank PJT Partners and law firm Jones Day. Representatives for those firms declined to comment or didn't provide an immediate response. Liberty spokeswoman Courtnee Chun didn't immediately provide comment; the company is advised by investment bank Millstein & Co. and law firm Weil Gotshal & Manges.
Active talks still continue with lenders, noteholders and financial sponsors, iHeart said in a regulatory filing that disclosed the latest skipped payments.
Negotiators have narrowed many of their differences, with the two sides swapping increasingly similar plans for a bankruptcy. But a deal has been held up by the insistence of iHeart's private equity sponsors on retaining a stake in the reorganized company.
Meanwhile, iHeart and creditors are positioning themselves for what could come after a the bankruptcy filing, with the company disclosing a bonus plan for Chief Executive Officer Bob Pittman and junior bondholders controlling more than US$200 million of unsecured debt suing in a New York state court.
They're accusing iHeart of secretly using assets for years to secure other borrowing. The suing bondholders include funds run by Angelo Gordon & Co., a distressed-debt investor that had been accumulating shares of iHeart's billboard advertising company, Clear Channel Outdoor Holdings Inc.
IHeart's 14 per cent bonds due 2021 fell 0.75 cents to trade at 12.25 cents on the dollar Thursday, according to Trace bond-price reporting. The shares fell 12 cents to trade at 43 cents a share at 12:44 p.m. in New York.