One of the favorite pastimes for sports fans is commiserating over the worst contract their home team ever made; guffawing over management’s decision to waste tens of millions of dollars for a player who never justified the huge payday. (See: Gilbert Arenas.)

For talk radio, there’s probably only one contract that enters that realm of notoriety: Rush Limbaugh’s eight-year, $400-million deal, signed in the summer of 2008 with his longtime radio employer Premiere Radio Networks.

Owned by Clear Channel Communications, which has since changed its name to iHeartRadio, Premiere’s Limbaugh deal instantly dwarfed any payout in AM/FM history. (Only Howard Stern’s contract with Sirius was larger.) The contract, which included a staggering $100 million signing bonus, never panned out as the wheels began to come off Limbaugh’s radio empire.

This year, his contract is up and the timing couldn’t be worse. The talker is facing ratings hurdles, aging demographics, and an advertising community that increasingly views him as toxic, thanks in part to his days-long sexist meltdown over Sandra Fluke in 2012. (He’s also stumbling through the GOP primary season.)

Concurrently, iHeartRadio’s parent company, iHeartMedia, is heading to court, teetering on bankruptcy. The once-dominant radio behemoth is saddled with $20 billion in debt, thanks to a misguided leveraged takeover engineered by Bain Capital in 2008, the same year the radio giant inked its disastrous Limbaugh deal.

Today those two defining missteps from the past are crossing paths, which means Limbaugh’s radio future has never looked less bright. This, as Limbaugh passes his 65th birthday, which seems to mirror his audience’s age.

“Who would even want someone whose audience is aging and is considered toxic to many advertisers,” asked RadioInsight last year.

Some industry insiders are wondering if his AM days are over and if Limbaugh’s futures rest with satellite radio, where advertiser indifference wouldn’t penalize him. The problem? His audience is so old. “With the aging and decline of Limbaugh's audience, Sirius may not be as viable an option as it once was,” Darryl Parks tells Media Matters. A former talk radio host, programmer, and self-identified Republican, Parks writes about the industry at DarrylParksBlog.

Indeed, the conservative talk radio format has morphed into the Classic Rock of talk; super-serving the same aging demo for the last twenty-plus years.

“Everything needs to evolve, but stations, conservative talk hosts and programmers have decided to double down and focus on the aging Baby Boomers,” says Parks. “When a group is no longer appealing to advertisers, that spells the end of any radio format.”

The former Clear Channel network owns 850 radio stations across the country and the syndication rights to right-wing stars such as Limbaugh, Glenn Beck and Sean Hannity.

During the late 1990s and early 2000s the company, feasting on the fruits of media deregulation, gorged itself with profits. (It also bullied the music business for years.)

Since then, not so much. And what a brutal ride it’s been for investors:

Clear Channel stock price, January 2000: $90.

Clear Channel stock value, April 2007: $39.

iHeartMedia stock price, July 2011: $8.30.

iHeartMedia stock price at close of yesterday: $1.15.

The company hasn’t reported a profit since 2007. Today, iHeartMedia is busy selling off assets in an effort to shore up its bottom line. “It’s a case of burning your sofa to heat up the house,” Philip Brendel, a credit analyst recently told Bloomberg. “It’s not necessarily a good idea but you’re running out of options.”

The company’s woes date back to the Clear Channel leveraged buyout deal in 2008. It was overseen by private equity giants Thomas H. Lee Partners and Bain Capital, once headed by Mitt Romney. Coming just months before the U.S. financial crisis of September 2008, the Clear Channel deal couldn’t have been hatched at a worse time.

How bad was the deal? Monumentally bad:

In 2007, the company, then called Clear Channel, reported a net income of $939 million. In the years since the LBO, the company has reported losses of between $220 million and $4 billion per year. For 2015, it reported a loss of $738 million.

Today, the interest paid on iHeartMedia’s massive debt gobbles up earnings. “Revenue last year was $6.5 billion. A $1.74 billion interest expense drove a net loss of $661 million,” Billboard reported. (iHeartMedia also operates a huge billboard advertising and live concert business, among other interests.)

Is this a company that can continue to fill wheelbarrows full of cash and pay Limbaugh $38 million annually, and bless him with another $100 million signing bonus? No way.

In fact, iHeartMedia’s too busy putting out other raging fires right now -- like trying to stay solvent.

What sparked the sudden specter of bankruptcy was an allegedly deceptive move made by iHeartMedia: Shifting money from one division of the business to another instead of paying debts owed to creditors.

The creditors went to court and sued. They “believe the stock transfer constitutes a default and might call their debt within 60 days,” Billboard reported. iHeartMedia sought an emergency injunction, stressing that if creditors won their “default” claim, the dominoes would instantly fall and iHeartMedia would face an avalanche of bond defaults totaling $15 billion to a long line of creditors. Those are payments the company simply cannot make, which would mean bankruptcy for iHeartMedia.

Having secured a temporary restraining order to halt the creditors’ actions, the two sides are set to square off in a courtroom next month to determine the outcome of the injunction request.

“It’s not a question of whether it collapses but when, and it’s likely to come sooner rather than later,” suggested Media Life. “It could be within months."

Meanwhile, not only has the bottom line for Limbaugh’s corporate radio home cratered since 2008, but the talker’s own business plan has become riddled with holes in recent years.

Just look at Boston, where Limbaugh stood out as a talk radio star for years. In 2015, his affiliate there dropped his midday show. Although not unheard of in the radio business (Limbaugh’s show is very expensive for stations to carry), what was surprising was that nobody else in Boston stepped forward to pick up Limbaugh’s program. Desperate not to lose coverage in the tenth largest radio market in America, iHeart shipped Limbaugh’s show down to a has-been station the company owns in Boston. Today, that station ranks 26th out of 29 stations in the market, boasting a .2 rating.

Those aren’t the kind of major market ratings you want to take to the negotiating table for a new contract.