Clear Channel will use proceeds from the February debt issuance, funds from a revolver and cash to pay down a loan that comes due in July 2014. The new debt will not mature until 2021.

While CEO Bob Pittman repositions the radio group for new media, the company has taken advantage of the credit markets to make roughly $20 billion in debt more manageable.

The San Antonio company and its private equity backers still face substantial challenges, the most daunting of which is $10 billion in debt that matures in 2016. The options include more financings, distressed-debt exchanges, and perhaps more equity from PE backers Bain Capital LLC and T H. Lee Partners LP, whose equity is arguably under water.

"We were very, very aggressive last year with over $7 billion of refinancings in favorable markets," Clear Channel CFO Thomas Casey said on the company's fourth-quarter earnings call in February.

Casey described Clear Channel's strategy as a "balancing act" of repaying or refinancing debt while the company invests in initiatives such as its iHeartRadio online venture.

Clear Channel is the largest U.S. radio group, with 840 stations, which are concentrated in the top 100 markets, and has an 89% stake in Clear Channel Outdoor Inc. among its holdings. The company generated $6.3 billion in 2013 revenue.

But Clear Channel also has more than $20 billion in long-term debt.

About half of the debt matures in 2016. In January of that year, $8.2 billion in term loans come due. There is a $1.9 billion maturity of senior unsecured notes in August 2016.

"There could be a combination of things," Scott Van den Bosch of Moody's Investors Service said regarding the options for the 2016 maturities.

Clear Channel could sell assets, exchange distressed debt for equity or draw cash from Clear Channel Outdoor. The company has tapped the outdoor unit for liquidity a number of times in recent years.

Van den Bosch suggested it was unlikely that Bain Capital and T.H. Lee will put in more equity unless Clear Channel's enterprise value were roughly equal to or exceeded its debt level.

"We believe the equity value is under water by about $2 or $3 billion," he said. "I don't think there is an incentive to put equity in currently."

The sponsors and other equity owners had reportedly owned $2.3 billion in debt as of early last year. Clear Channel's unrestricted subsidiaries have also bought back some of its own debt.

"Those could be equitized," he said of the debt, an exchange of which for equity would require consent from lenders.

Clear Channel Outdoor, meanwhile, still has some room to take on more debt.

"We expect them at some point to do about $500 million of issuance at Outdoor and pay a dividend," Van den Bosch added. "Clear Channel will use their 89% of the proceeds to pay down debt."

Bain and T.H. Lee took Clear Channel private in 2007 through a $24 billion LBO. Clear Channel's total leverage is roughly 11.5 times Ebitda, according to Moody's.

The company's secured leverage comes to 5.9 times Ebitda, an improvement from a multiple of 6.9 at the end of 2011.

Secured leverage is an important metric for Clear Channel. The number reflects secured debt minus cash and equivalent holdings. The company's debt covenants limit secured leverage to 9.5 times Ebitda. Even when the covenants reduce the threshold for secured leverage to 9.25 in June, Clear Channel will have a cushion.

"They've done an excellent job -- with the caveat that there is still more wood to chop," said CRT Capital Group LLC analyst Lance Vitanza.

The company has been "very creative" in managing its balance sheet since the LBO, Vitanza explained.

"It is much more likely today that they grow into their capital structure than it was a few years ago," he added.

In all but one of the nine quarters since Vitanza began following the company, Clear Channel has met or exceeded his Ebitda estimates.

If the broadcaster continues to hit his projections, Vitanza said, it would finish 2016 with a total leverage multiple in the high 8's.

"That would, to me, suggest that there is an excellent chance they will be able to figure something out," he said. "At 8 times, that is not an insurmountable problem, at least in these capital markets."

If there is another recession, he cautioned, "all bets are off."

Moody's said that radio and outdoor have "heightened sensitivity" to the larger economy.

"If the economy is strong enough and the performance is good enough, they could get through this," Van den Bosch said. "The stronger the results are, the more options they have."

Clear Channel did not respond to calls or e-mails.