Fortune 500 rank: 278
2010 revenue: $8.8 billion
10-year annualized return: -27.9%
A&P, the country's oldest grocer, used to be as well-known as Wal-Mart. The company had thousands of store locations in its heyday; it also pioneered the idea of the store brand (one of its innovations was Eight O'Clock Coffee), now a ubiquitous concept in the retail industry.
In recent years, however, A&P struggled to compete with low-cost warehouses and drugstores, and its store count dwindled to just a few hundred. Saddled with a large debt load, significant pension obligations, and supply chain problems, A&P filed for bankruptcy in December 2010.
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Last updated May 05 2011: 2:52 PM ET