Fortune 500: 20 companies that lost the most

1 Caesars Entertainment

Caesars casino and hotel in Las Vegas.

Fortune 500 rank: 318
2013 loss (millions): 2,948.2

Gaming company Caesars Entertainment most definitely does not like the hand it’s been dealt in Atlantic City, where it operates four casinos. Competitors are fighting over the local market’s shrinking pot of revenues -- down 42% since 2007, according to New Jersey’s Casino Control Commission -- while real estate prices for casino properties have fallen off a cliff. The Atlantic Club, purchased by hedge fund Colony Capital for $513 million in 2005, went for $23.6 million in a December bankruptcy sale. Eying local realty transactions, Caesars recorded $2.36 billion in impairment losses on its Atlantic City properties, which include the brands Harrah’s and Showboat, and CEO Gary Loveman has indicated he may close one of them in the future.

2 Energy Future Holdings

Fortune 500 rank: 438
2013 loss (millions): 2,587.0

Energy Future, the biggest power company in Texas, can claim an ignominious distinction in the annals of American business history: Warren Buffett considers his nearly $2 billion investment in the company’s bonds one of the biggest mistakes he’s ever made. “Most of you have never heard of Energy Future Holdings,” Buffet told shareholders in his annual letter this year. “Consider yourselves lucky; I certainly wish I hadn’t.” A product of the largest private equity deal ever, Energy Future (formerly TXU) is heavy with debt and struggling to compete, since the boom in natural gas production has put a lid on electricity prices. Buffet lost close to $900 million on his bet, but the Oracle did get one prediction right: Energy Future filed for bankruptcy protection in April.

3 Newmont Mining

Fortune 500 rank: 327
2013 loss (millions): 2,462.0

Gold lost its sheen last year, with prices tumbling 28% -- their most precipitous annual drop in over three decades -- as investors abandoned the precious metal to chase returns in the soaring equities market of 2013. Gold producers like Newmont had to cope with the fallout. Asset impairment charges drove the Colorado-based outfit’s net loss: The company recorded a pair of $2.1 billion write-downs on its Long Canyon mine in Nevada and its Boddington operations in Australia. Newmont and Canadian gold conglomerate Barrick discussed joining forces as recently as April, but the merger talks have since stalled.

4 Alcoa

Fortune 500 rank: 130
2013 loss (millions): 2,285.0

Last year was a spell of reckoning for Alcoa: Facing both lower metal prices and higher costs for the raw material alumina, the company began closing some smelting operations located in the U.S. and Canada, while curtailing others in Brazil. Ultimately, Alcoa decided the outlook for its Primary Metals unit had grown too dim. It valued the division’s goodwill at zero, and recorded an impairment charge of $1.7 billion. The company also closed the door on a long-running anti-bribery case involving contracts with Aluminum Bahrain, and faced up to a $243 million after-tax charge stemming from settlements with the Department of Justice and the Securities and Exchange Commission.

5 American Airlines Group

Fortune 500 rank: 112
2013 loss (millions): 1,834.0

Like a pair of heartened newlyweds, American Airlines and US Airways merged in December with great optimism about their chemistry and future earnings potential -- even if they did have to account for some old baggage first. The new American recorded $3.1 billion in net special charges, largely related to the old American’s bankruptcy reorganization and costs of the merger itself. Had such one-time items not existed, American said, the two airlines would have produced a combined $1.9 billion profit for the year, up from a combined $407 million in 2012. Those are non-GAAP measures, but they are results this couple is certainly proud to announce.

6 United States Steel

Fortune 500 rank: 166
2013 loss (millions): 1,672.0

Grappling with a lackluster demand for steel in a slow-to-recover global economy, Pittsburgh-based U.S. Steel tapped chief operating officer Mario Longhi (an Alcoa alum) to replace John Surmaas CEO last September. Longhi took the helm with a commitment to streamlining and cutting costs (a plan dubbed “Project Carnegie,” for the legendary Andrew, of course). The company also absorbed $1.8 billion in goodwill impairment charges: $969 million for its flat-rolled reporting unit and $837 million related to its tubular segment. Anticipating as well that it would permanently halt steel production at its Hamilton mill in Ontario, Big Steel recorded $302 million worth of shutdown charges in the fourth quarter.

7 NII Holdings

Fortune 500 rank: 495
2013 loss (millions): 1,649.6

When Sprint deactivated its old-school Nextel iDEN 2G network in the U.S. last June, south-of-the-border consequences fell on NII. The company, located in Reston, Va., operates the walkie-talkie-like Nextel service in four Latin American countries, including Mexico. Sprint's move prompted many customers, particularly those living near the U.S. border, to drop NII after it failed to roll out a convincing 3G alternative, causing its Mexico subscriber base to fall 16%. The company has meanwhile warned investors that it may not have enough liquidity to fund the business through 2015.

8 Supervalu

Fortune 500 rank: 94
2013 loss (millions): 1,466.0

Seeking to regain an edge in the fiercely competitive grocery industry, Supervalu off-loaded five of its retail chains in March 2013, selling Acme, Albertsons, Jewel-Osco, Shaw’s, and Star Market to a Cerberus-led investor group. No wonder, considering that operations at that collection of stores experienced an 8.2% drop in annual sales and accounted for $1.2 billion of the company’s losses. Supervalu, located in Eden Prairie, Minn., also eliminated some 1,100 positions over the past year. The leaner mode may be paying off for CEO Sam Duncan (who formerly ran OfficeMax and took over in January 2013), as he led Supervalu to a $26 million profit in its most recent fiscal quarter.

9 J.C. Penney

Fortune 500 rank: 235
2013 loss (millions): 1,388.0

Among the lowlights of the retailer’s continuing, soap-operatic slide in 2013: CEO Ron Johnson resigned in April after all of 16 months on the job; the company had to apologize to customers for alienating them with new store concepts; and activist investor Bill Ackman, who stepped down from the board in August, swallowed a $470 million loss upon selling his Penney’s stake. With former chief executive Myron Ullman III now back at the helm, same-store sales in the fourth quarter inched up 2% from the same period a year prior, though a healthy turnaround remains a long way off.

10 Sears Holdings

Fortune 500 rank: 87
2013 loss (millions): 1,365.0

Chairman and CEO Eddie Lampert has displayed little, if any, desire to invest in his brick-and-mortar fleet of Sears and Kmart operations. The company has been in free fall, with sales plummeting by $3.7 billion last year. Sears attributes about a quarter of its lost revenue to having fewer stores in operation, with more than 300 locations gone since 2010. Lampert, who is bent on bolstering sales through a loyalty program called “Shop Your Way,” say his way to shuttering Sears' Chicago flagship this past January.

11 Toys “R” Us

Fortune 500 rank: 223
2013 loss (millions): 1,039.0

The nation's largest specialty toy retailer suffered a rough 2013 on stepped-up competition from discount rivals and -- believe it or not -- lower birth rates. Revenue dropped $1 billion, while same-store sales fell 5% in the U.S. as Wal-Mart and Amazon stole market share. Also cutting into top-line growth according to the company: Fewer babies were born after the Great Recession hit in 2008. Those Toys “R” Us kids that never were would have been up to five years old in 2013, which is a key age-group for the retailer. Company veteran Antonio Urcelay took over as CEO last year and plans updates for both stores and online, but he has said he does not see major closings.

12 Navistar International

Mahindra Navistar trucks on an assembly line in Maharashtra, India.

Fortune 500 rank: 259
2013 loss (millions): 898.0

Government austerity turned into a speed bump last year for Navistar, which makes military vehicles, as well as school buses and long-haul freight trucks. Since 2011, sales to the U.S. Defense Department have fallen more than $1 billion on the heels of Pentagon budget cuts. A new strategy to tackle federal standards for engine emissions has also run up to more than $700 million, while Navistar is expected to pay warranty costs on prior engines until the end of next year.

13 First Data

Fortune 500 rank: 261
2013 loss (millions): 869.1

The world’s largest payment processing company has something of a cash flow problem. Private equity firm KKR & Co. bought First Data in 2007 in a highly leveraged deal for $29 billion. A consistent stream of layoffs and financial losses have followed. Without significant revenue growth the company has been unable to offset the interest it pays on its heavy debt load, but First Data has hinted that an IPO could be on the horizon, Bloomberg reports, which would raise some much-needed funds.

14 Prudential Financial

Fortune 500 rank: 72
2013 loss (millions): 667.0

One of the nation’s biggest insurance providers, Prudential Financial faced a rough year at its core unit. Increased investment income was unable to offset a more than 60% drop in revenue from premiums. The company gets a sizeable chunk of its profits overseas and has been suffering from negative currency trends -- especially from the Japanese yen. Things may be looking up, however. Prudential swung to a 2014 first-quarter profit, boosted by a strong showing in its retirement services business.

15 CC Media Holdings

Fortune 500 rank: 419
2013 loss (millions): 606.9

Many Americans couldn’t wait to get the media blitz of the 2012 election behind them. CC Media Holding was not among them. The parent company of Clear Channel Communications, one of the nation’s biggest radio station and outdoor advertising firms, saw its 2013 loss widen as political spending dropped without a presidential election to drive results. Growth in the company’s Media & Entertainment and Americas outdoor divisions was further offset by declines in its International outdoor unit. Bright days may be ahead for CC Media however. The upcoming midterm races are expected to be some of the most expensive elections in recent memory.

16 Peabody Energy

Peabody Energy building in St. Louis.

Fortune 500 rank: 365
2013 loss (millions): 524.9

To say 2013 was a bad year for coal would be an understatement. Global production grew only 2%, as the Obama administration announced strict new rules limiting carbon emissions by coal plants. Revenue dropped 14% at Peabody, the nation’s biggest coal producer, as its net loss shrank. The company expects coal demand to rise in the coming year, but relatively low natural gas prices will continue to add downward pricing pressure.

17 NRG Energy

Plug Power sells fuel cells for forklifts to companies such as Procter & Gamble and Wal-Mart, which recently ordered 1,700 of the units.

Fortune 500 rank: 244
2013 loss (millions): 386.0

Despite a 34% jump in revenues, the New Jersey-based energy company slid to a loss from a year-ago profit due in large part to impairment charges on plants in Delaware and Australia. NRG completed a number of acquisitions in the first quarter of 2014 to boost operations and to widen its offerings into renewables. CEO David Crane is betting big on solar with plans to turn his company into an industry leader.

18 CenturyLink

Fortune 500 rank: 158
2013 loss (millions): 239.0

Growth from CenturyLink’s broadband, hosting, and TV customers wasn’t enough to outweigh decreased income from higher-margin legacy services, which led the Louisiana-based telecom to swing to a full-year loss from a 2012 profit. The company has big plans for cloud computing, however, and is going head-to-head with market leaders like Amazon and Microsoft by beefing up its infrastructure and offering highly competitive pricing.

19 HD Supply Holding

Fortune 500 rank: 317
2013 loss (millions): 218.0

The former professional services division of Home Depot sharply reduced its net loss last year as it trimmed costs while posting a 5% rise in revenue. Severe winter weather in the fourth quarter weighed on results, while a large part of HD Supply’s loss included $87 million spent to pay down and modify its debt. The company has been working hard to deleverage itself. A $1.1 billion IPO last June went toward improving its balance sheet.

20 Charter Communications

Fortune 500 rank: 331
2013 loss (millions): 169.0

The nation’s fourth-largest cable provider managed to narrow its annual loss by nearly half in 2013, largely on a rise in revenue from TV and Internet customers. But the big story was its failed bid for Time Warner cable. After months of overtures, Charter’s $37 billion offer for its rival was soundly rejected last January. A month later Comcast bid $45 billion, and Time Warner said yes. Charter isn’t left entirely out in the cold. To ease antitrust concerns, the company is picking up 3.9 million subscribers from Comcast and Time Warner.

Subscribe to Well Adjusted, our newsletter full of simple strategies to work smarter and live better, from the Fortune Well team. Sign up today.

Read More

CryptocurrencyInvestingBanksReal Estate