By Ryan Dezember And Daniel Gilbert 

Shortly after bagging big profits on a Pennsylvania drilling deal, George Roberts traveled to Houston to meet with the banker who had brought the prospect to his private-equity firm, KKR & Co.

Mr. Roberts, KKR's co-founder, asked about other opportunities in shale drilling. Ralph Eads unfurled maps on a conference-room table and pointed out the country's emerging drilling fields. "We want to be your first call," Mr. Roberts told the Jefferies Group LLC banker.

KKR went on to complete a couple of relatively small but hugely profitable shale deals before Jefferies in 2011 pitched the big one: Samson Investment Co., one of the largest closely held energy producers in the U.S. KKR bit, in the biggest-ever buyout of an oil-and-gas company.

Now, the investment is deep in the red, as falling oil prices amplify struggles Samson has faced since its $7.2 billion acquisition. Almost immediately after the deal closed, natural-gas prices plunged to their lowest level in a decade, hurting profits. Meanwhile, the Tulsa, Okla., company, now known as Samson Resources Corp., had to contend with $3.6 billion of debt it took on in the takeover.

The dive in oil prices has crimped Samson's cash flow further and could make it harder to find buyers for oil-and-gas fields the company is trying to sell to make ends meet. Samson has lost more than $3 billion since the buyout, including a $470.7 million loss this year through September.

Samson's woes stand as a cautionary tale of the U.S. shale boom. Fed by cash from Wall Street and private-equity firms, drillers in recent years rushed to tap new oil-and-gas deposits across the country--and contributed to the collapse in prices for both fuels. Samson's woes have been exacerbated by the very tools private-equity firms use to juice their returns: Samson carries debt used to fund its own purchase and pays fees to its owners. Last week, Moody's Investors Service downgraded Samson's credit rating while taking the unusual step of simultaneously flagging the company for further downgrade.

"It speaks to our level of concern," said Andrew Brooks, a Moody's senior analyst. "There's no question that the interest burden this company is carrying is excessive."

For the most part, private equity has been a friend to shale drilling, which emerged about a decade ago. Wildcatters combined sideways drilling done miles beneath the surface with a rock-cracking process called hydraulic fracturing to unlock vast reserves of fuel. Private-equity firms were poised to profit. At the time, major oil companies had turned away from the U.S. in pursuit of far-flung prospects, and bank financing all but dried up during the recession. The financiers, meanwhile, had piles of cash raised before the financial crisis for buyouts.

Early successes brought hunger for more deals. Private-equity investors have dedicated more than $100 billion to specialized energy funds since the end of 2011, according to data provider Preqin.

Many investments remain in the black. But the nearly 50% drop in oil prices since this summer has wiped at least $12.7 billion of value from private equity's holdings, based on the stock moves of nine exploration and production companies that represent some of firms' largest publicly traded energy positions.

An investment group led by Warburg Pincus LLC that launched Appalachian gas producer Antero Resources Corp. seven years ago with $1.5 billion was up more than $12 billion until recently. Since June, the firms' shares in Antero are down 34%, or about $4.6 billion.

EP Energy Corp., subject of a leveraged buyout nearly as large as Samson's, is down 63% since June, erasing about $2.6 billion of value from the stake held by its private-equity backers, led by Apollo Global Management LLC. That deal is teetering around break-even for the buyout group.

The damage hasn't reduced the appetite for oil-and-gas deals among buyout barons, they say. "I'm glad we're in the position that we are, as prices have come down significantly," Henry Kravis, KKR's co-founder and with Mr. Roberts, co-CEO, said at a conference earlier this month. "We see this as a real opportunity."

But at Samson, analysts say, the company will have exhausted all but a sliver of its available credit and run afoul of debt agreements by early 2016, barring a rise in oil-and-gas prices, an injection of cash from its private-equity backers or better-than-expected proceeds from asset sales.

The $4.1 billion that KKR and its partners put into the buyout shriveled to about one-quarter of that by the end of September, according to Samson's securities filings. Some of Samson's debt is trading at 42 cents on the dollar.

Private-equity firms such as KKR can be masters at sustaining their investments through economic cycles.

Samson has embarked on a strategy of "shrinking the company to a set of assets that can grow," Chief Executive Randy Limbacher told investors last month. It is selling properties in Oklahoma, North Dakota, Wyoming and Colorado.

KKR has been on the winning and losing sides of energy deals. One costly blunder it led: a $32 billion bet on Texas power producer TXU Corp., now known as Energy Future Holdings Corp., in a 2007 megabuyout.

Then, too, natural-gas prices soon swooned, and KKR and its deal partners were left with an overly indebted company. After many years of financial moves to delay a bankruptcy, the company filed for such protection this past April.

Still, the ill-fated deal gave KKR an education in the potential of new drilling technology. Rather than retreat, KKR executives jumped into investing in oil-and-gas production.

In 2009, tipped by Mr. Eads, KKR invested $312 million in East Resources Inc., a closely held gas producer with shale acreage in western Pennsylvania and Ohio that needed money to drill. About a year later, East was sold, fetching $1.5 billion for its stake. Along with two other small shale deals, KKR reaped more than the roughly $2 billion the firm lost for it and its investors at Energy Future. KKR pushed further, opening a Houston office and staffing it with engineers and geologists to vet drilling prospects.

Samson, based in Mr. Kravis's hometown, was founded by Charles Schusterman in 1971 and was being run by his daughter, Stacy Schusterman, when it hit the auction block.

Samson's debt ballooned with the deal, though KKR and its partners paid more than half of the price with cash, using much less debt than is typical in leveraged buyouts. Lenders typically require more upfront cash in energy deals to protect against falling commodity prices.

Those concerns were well-placed. Within a month of the buyout being completed, KKR experienced a TXU redux: U.S. natural-gas prices dropped, crimping Samson's cash flow.

Meanwhile, the company had big interest expenses for the takeover debt. Samson also began paying so-called management fees to its private-equity owners that began at $20 million annually and increase by 5% a year.

To cut costs, Samson laid off 120 employees. It embarked on asset sales that have so far brought in more than $1 billion. It is currently shopping assets that account for about 25% of its production and are expected to bring in as much as $1.1 billion, Barclays analysts estimated last month. Samson said it has also reduced drilling costs.

KKR and its partners last year rolled out a big pay package to lure Mr. Limbacher, a veteran of big energy producers, according to a securities filing. His 2013 compensation was valued at $56.6 million, more than the CEOs of Exxon Mobil Corp. and Chevron Corp. made combined.

Yet most of his compensation was paid in Samson stock that vests over five years. Samson's woes have slashed the value of those shares, and in an effort to retain employees, executive pay plans were revamped last month to include more cash in light of the stock's swoon and a faster -vesting timetable for the stock.

"At least one of my co-workers suggested to me that God brought me here to teach me humility," Mr. Limbacher said on a recent analyst call when asked whether he and his team would stay at the struggling company.

As for Samson's sellers, the Schustermans have remained in the oil business, operating assets along the Gulf Coast through its Samson Energy Co.

"Selling a family business like Samson was one of the most difficult decisions we have ever made," said Ms. Schusterman. "Oil-and-gas pricing is currently lower than anyone anticipated, including us. Despite current pricing, we remain optimistic concerning the long-term profitability of the oil and gas business, and there are so many great assets and people at [the company] to generate positive results."

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