are renowned for innovation, phenomenal growth, and, in the case of public corporations, their soaring share prices. Google Inc. (NASDAQ: GOOG) usually makes the list, as does Apple Inc. (NASDAQ: AAPL). At the other end of the scale are well-known firms that are so crippled they go bankrupt or disappear entirely. Recently, these have included AMR, the parent of American Airlines, Borders, and Eastman Kodak.


1. J.C. Penney Company Inc. (NYSE: JCP)

J.C. Penney, founded in 1913, counted itself among the primary retailers and catalog companies in the US for decades. But under CEO Myron Ullman III, who took over in 2004, its revenue began to slide, dropping from $19.9 billion in 2007 to $17.3 billion in 2011. Earnings fell from $1.1 billion to a loss of $152 million in the same period. J.C. Penney’s share price has fallen 70% in five years. By way of contrast, the shares of Macy’s Inc. (NYSE: M) and Target Corp. (NYSE: TGT) — two direct competitors — have been essentially flat over the same period. J.C. Penney was challenged by these two companies and several others, including Wal-Mart Stores Inc. (NYSE: WMT) and Costco Wholesale Corp. (NASDAQ: COST). Problems became so severe that J.C. Penney closed its formerly successful catalog business and reached outside for a new CEO. The board’s choice was Apple Retail Chief Ron Johnson, who was picked in June 2011. Johnson changed the company’s pricing structure, but the reaction was so poor that revenue dropped an extraordinary 20.1% to $3.2 billion in the first fiscal quarter. J.C. Penney posted a loss of $163 million. Internet sales, so essential in a world in which Inc. (NASDAQ: AMZN) has become a significant presence, fell 27.9% to $271 million. By contrast, Macy’s total sales, combining online and those made in stores, rose 4.3% to $6.1 billion in the last reported quarter. And Macy’s is hardly J.C. Penney’s largest competitor by revenue or workforce. Walmart’s sales were $450 billion last year, while Costco’s were $89 billion.

2. The New York Times Co. (NYSE: NYT)

The New York Times is, and has been for decades, the premier daily newspaper company in the US. But the company has been shrinking rapidly. Ten years ago, The New York Times Company made $300 million on revenue of $3.1 billion. Last year it lost $40 million on revenue of $2.3 billion. The New York Times did not move online fast enough to offset the rapid erosion of print advertising. Its tardiness allowed it to be challenged on the Internet by properties like The Huffington Post, Google News, and the news, sports, and financial properties of portals such as MSN, AOL, and Yahoo!. As an indication of how the stock market measures the value of The New York Times Company, its market cap is $1.2 billion against its revenue of $2.3 billion in 2011. Low-brow content aggregator Demand Media has a market capitalization of $865 million against 2011 revenue of $325 million. Demand lost $13 million last year. The reason the market values of the two companies are so close? The Times still relies on the dying print business for the lion’s share of its revenue. Its market cap and cash balance are too low to allow it to more aggressively move to the internet or buy large online properties. In the last quarter, The Times’ revenue was roughly flat at $515 million. The company lost 57 cents a share compared with a profit of 5 cents a share in the same period last year. The worst news from the quarter was that “Digital advertising revenues at the News Media Group decreased 1.6 percent to $52.6 million from $53.5 million mainly due to declines in national display and real estate classified advertising revenues.” The Times did make advances in online paid subscriptions, but circulation revenue barely offset the drop in advertising sales. At the heart of The New York Times’ uniqueness among American newspapers is the quality of its editorial content. The company has held the line on retaining its large editorial staff. It did lay off 100 people in 2009, which was about 8% of the news staff. The industry is in the midst of another wave of job cuts. The Times has not been able to show significant top-line growth, even with its digital subscription efforts. Print is in too much of a shambles for the company to shore itself up in the digital world.

3. Groupon Inc. (NASDAQ: GRPN)

Groupon is an unlikely candidate for a list of companies that have their best years behind them. One reason Groupon belongs on this list is its stock price has fallen by well over 70% since its November 2011 IPO. Groupon’s primary problem is that the online coupon business, in which it was the major pioneer, is a commodity business now. It has not been terribly difficult for Amazon and other large retailers like Walmart to enter the sector. Groupon was the most significant player in its industry after beginning operations in 2009, when it posted revenue of only $15 million. That number rose to over $1.6 billion last year, but Groupon paid dearly for that growth. The company lost $675 million over that same two-year period before interest and taxes. Groupon’s revenue grew 89% to $559 million in the most recently reported quarter. But expansion continued to come at a cost. Groupon’s bottom line grew from a loss of $12 million in the same quarter last year to one of $147 million. Groupon’s new competitors replicated most of its tactics very quickly. LivingSocial, the rival most like Groupon in terms of its business model, had 7.2 million unique visitors last year to Groupon’s 11 million, according to online industry research firm Comscore. LivingSocial has financial support from Amazon. Google has entered the sector with a product called Google Offers. Well-regarded industry website VentureBeat lists 33 direct competitors to Groupon, and none is a large corporation. The Chicago Sun-Times, one of the two daily papers in the city where Groupon is headquartered, summed up Groupon’s difficult challenges: “Groupon has been weighed down by high marketing and staffing costs and faces increasing competition from the likes of and Living Social, among hundreds of other local deals sites.” Even the hometown press has nothing positive to say about the company.

4. Sprint Nextel Corp. (NYSE: S)

Sprint finally posted some reasonably good results recently. However, these could not mask the fact that the No. 3 wireless carrier is too small to ever gain any ground on AT&T Inc. (NYSE: T) and Verizon Wireless (VZ). Sprint’s revenue rose rapidly from 2002 to 2006. Over the period, sales moved from $15.2 billion to $41 billion, aided by the buyout of Nextel at the end of 2004. Sprint paid $35 billion for Nextel, and the decision turned out to be a disaster. The Sprint network ran on a different platform from Nextel’s. Customers left the combined company. Sprint made the MSN “Customer Service Hall of Shame” several times, most recently in 2010. Sprint’s customer service ratings have improved significantly since then, but the damage has been done. While AT&T and Verizon Wireless have grown rapidly, Sprint’s revenue has fallen from $41.1 billion in 2007 to $33.7 billion last year. Sprint’s cumulative loss during that period was over $43 billion. Sprint now has about 50 million subscribers to Verizon’s 104 million and AT&T’s 95 million. As a Morningstar researcher recently noted, “While Sprint has struggled, Verizon Wireless and AT&T have benefited at its expense. Fending off these much larger rivals will be increasingly difficult as data services become more important to the industry.”


5. Barnes & Noble Inc. (NYSE: BKS)

The cause of Barnes & Noble’s downfall can be described in a word: Amazon. In 2002, Barnes & Noble made $109 million on sales of $4.9 billion. That same year, Amazon lost $149 million on revenue of $3.9 billion. Fast forward to 2011 when Amazon’s revenue reached $48.1 billion and it earned $631 million. Barnes & Noble lost $69 million on $7.1 billion last year. Amazon may sell consumer electronics equipment and internet streaming video products, but at its heart it is still the world’s largest bookstore. The highlight of Amazon’s recent quarter, in which revenue rose 29% to $12.8 billion, was that “Kindle Fire remains the No. 1 bestselling product across the millions of items available on since launch.” The product most visibly promoted on the home page? The Kindle. Barnes & Noble’s legacy business is huge and expensive. As of its April proxy filing, the company operated 1,338 bookstores in 50 states, including 647 bookstores on college campuses. Obviously those stores require inventory, rent and personnel. And Barnes & Noble mentions “the maturity of the market for traditional retail stores” as one of the risk factors in its SEC filings. Is it any wonder that in its last fiscal year, Barnes & Noble had retail sales of $4.86 billion? That part of the company’s business shrank by 2%. Its Nook segment, which encompasses the digital business (including readers, digital content and accessories), had revenue of only $933 million. Digital sales rose 34% over the previous year but remain a very modest portion of sales. Barnes & Noble’s digital division is vulnerable. That is particularly clear when the market share of its Nook e-reader is taken into account. The Nook’s share of the US market is 27%, in contrast to a 60% share for Amazon’s Kindle and 10% for Apple, according to Reuters. Barnes & Noble is hopelessly outgunned online, and the retail book business has leveled off.

6. Zynga Inc. (NASDAQ: ZNGA)

Zynga, the premier social network game company, is another name that by all rights should not be on our list. Zynga’s revenue rose from $19.4 million in 2008 to $1.14 billion last year. Zynga spent plenty of money to reach the top position in its industry, and last year lost $404 million. Investors were drawn to the company because it had been effectively piggy-backing free and premium games onto the Facebook platform, which currently has nearly one billion members. The success of the model appeared to be astonishing. In its last reported quarter, Zynga says it had 192 million monthly unique users, up 27% from the same quarter a year before. But, as the total number of virtual games has grown, the cost to maintain a lead has become almost prohibitive. Zynga lost $23 million last quarter on revenue of $332 million. In the same quarter a year ago, Zynga made $1 million on revenue of $279 million. Zynga’s growth rate is no longer impressive, and the problems it faces, apparently, will soon worsen. The company recently lowered its outlook to reflect delays in launching new games, a faster decline in existing Web games due in part to a more challenging environment on the Facebook web platform, and reduced expectations for Draw Something. This bad news pushed Zynga’s shares to $3, down from a post-IPO high of $15.91. Zynga’s problems are more complex — and more permanent — than delayed games or lower returns on its Facebook presence. The game market is becoming more fragmented by the day as games migrate from consoles to PCs to tablets and smartphones. Social media is not the only place that game players gather in great numbers. Many of the most downloaded apps at the Apple App store are games. The same is true of the Google app store. Zynga’s insurmountable challenge was summed up by its CEO Mark Pincus on the company’s recent earnings call. He said, “We think social gaming is just starting to grow quickly on mobile and we think it has the potential to be the most important part of the experience on mobile and an even bigger business in the future.” Despite his vision of the future, Zynga’s shares are in the rubble. The reason, GameIndustry International reports, is that “Apple iOS and latterly Android have become the dominant platforms for growth in social gaming (not necessarily for social gaming itself, but all the growth is on mobile, not on the web)…” Zynga has been overwhelmed by hordes of new challengers.

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7. Dell Inc. (NASDAQ: DELL)

Dell is being hammered by the smartphone and tablet PC sectors. This is not long after its prospects were damaged by poor management decisions and the rise of Asian manufacturers, which has taken significant market share from the company. Dell was one of the companies that capitalized on the creation of the IBM PC platform. Among the others were Hewlett-Packard Co. (NYSE: HPQ), Compaq, and Gateway. International Business Machines Corp. (NYSE: IBM) exited the business when it sold its PC operations to China-based Lenovo in late 2004. After that, the PC industry went through two sets of transformations. One was consolidation: HP bought Compaq and Acer bought Gateway. The other was the emergence of large Asian PC businesses — Acer, Asus and Lenovo. All of these companies, Asian and American, face a substantial challenge today. PCs are viewed as commodities, which has put pressure on prices. Computing has moved quickly to smartphones and tablets. Dell made another substantial mistake. As its share of the global PC market has fallen, it has not aggressively followed the successful model adopted by IBM. IBM built a $100 billion business offering consulting, software, IT support, hardware and financing. It does not rely heavily on a single offering. Dell’s reliance on PC sales has continued to sting, particularly now that the PC era has given way to one dominated by smartphones.

8. Advanced Micro Devices Inc. (NYSE: AMD)

AMD’s latest quarterly report shows just how bad off the company is. Year-over-year revenue fell 10% to $1.4 billion. Non-GAAP net income fell from $70 million to $46 million. AMD was Intel Corp.’s (NASDAQ: INTC) most direct competitor five years ago, and held about 24% of the server and PC chip market in 2007. Last year, its market share fell to 19%. But that is not AMD’s single greatest problem. The company bought graphic chip maker ATI in 2006 for $5.4 billion. PC makers had begun to add more of these chips to their machines. AMD needed to keep pace with rival Intel and graphic chip maker Nvidia Corp. (NASDAQ: NVDA) The main result of the ATI transaction was that it saddled AMD with an unsustainable debt and did almost nothing to help AMD’s fortunes. AMD had revenue of $6 billion in 2007, while Intel’s was $38.3 billion. Last year, AMD’s revenue rose to only $6.6 billion, while Intel’s soared to $54 billion during the same period. AMD has had three CEOs in the last five years, as it struggled to find a strategy for growth. The company’s greatest challenge may lie ahead as much of the personal computing market moves to tablets and smartphones. The chip used in the Apple iPad was designed by Apple and made by Samsung. The Apple iPhone 5 will probably be powered by a quad core processor made by Samsung, the same chip used in the Samsung Galaxy S III. The other primary designers of the current generation of chips are Qualcomm Inc. (NASDAQ: QCOM) and ARM Holdings PLC (NASDAQ: ARMH). AMD’s products are almost nowhere to be found in this latest generation of portable devices.

9. Bank of America Corp. (NYSE: BAC)

Most of the operations that constitute Bank of America today were created through a series of mergers and buyouts, including the acquisition of FleetBoston in 2003 and credit card giant MBNA in 2005. These and other deals were engineered by Ken Lewis, who became CEO in 2001. By 2007, he had succeeded in making Bank of America the largest bank in the US by deposits. But Lewis became overzealous as he tried to make the bank even larger. As the financial system was heading toward near-collapse, Bank of America bought crippled mortgage bank Countrywide Financial in January 2008 and deeply troubled investment bank Merrill Lynch in September of that year. Bank of America’s financial troubles multiplied so rapidly that it was forced to take much more TARP money than most other large US banks — $45 billion. Lewis’s risk-taking eventually was part of the reason the federal government pressed the bank to add outside directors who had been regulators or heads of successful banks. In June 2009, four new directors were appointed, including a former member of the Board of Governors of the Federal Reserve System and a former chairman of the Federal Deposit Insurance Corporation. Lewis was out by the end of the year, and Brian Moynihan replaced him. But Moynihan’s tenure has been even more disastrous than Lewis’s. JPMorgan Chase & Co. (NYSE: JPM) passed B of A in assets to become the largest bank in the US. Crippling losses caused B of A to announce it would cut more than 30,000 jobs. In late 2011, a $50 billion class action suit was filed against B of A based on the lack of disclosures made when it bought Merrill Lynch. Bank of America has also been the target of several mortgage fraud suits, and entered into a settlement which cost it and four other large US banks a combined $25 billion. B of A still faces legal and balance sheet problems, which may force it to raise tens of billions of dollars. This will undermine the  share price. The final and most difficult challenge is its exposure to the US real estate market, which is unparalleled among its peers. This, in addition to the unhealed scars from poor management and the global financial collapse, have left Bank of America limping along.