17 of 20
17. Sprint Nextel
17. Sprint Nextel
Fortune 500 rank: 85
2010 revenue: $32.6 billion
10-year annualized return: -12.4%

It's been called one of the decade's worst acquisitions, and there's no argument here. In 2005 Sprint paid $36 billion for Nextel, then a high-flying wireless provider with a cool walkie-talkie function on its phones. By then Nextel had peaked in popularity, and just three years later Sprint wrote down Nextel's value by $30 billion.

Sprint Nextel is now in the process of closing Nextel's iDEN network for good. It's a long and expensive task, and a reminder of the steep price shareholders have paid for management's mistakes.

NEXT: 18. Gannett
Last updated May 05 2011: 2:52 PM ET
Top 50 Wal-Mart holds Exxon Mobil at bay and rules the Fortune 500 for the second year in a row. Which other companies made the top 50? More
They're hiring! These Fortune 100 employers have at least 350 openings each, totaling more than 96,000 jobs. What are they looking for in a new hire? More
20 most profitable Exxon Mobil rode high oil prices to a staggering $30 billion in profits. From Apple to Google, here are the other big winners. More
Market indexes are shown in real time, except for the DJIA, which is delayed by two minutes. All times are ET. Disclaimer LIBOR Warning: Neither BBA Enterprises Limited, nor the BBA LIBOR Contributor Banks, nor Reuters, can be held liable for any irregularity or inaccuracy of BBA LIBOR. Disclaimer. Morningstar: © 2014 Morningstar, Inc. All Rights Reserved. Disclaimer The Dow Jones IndexesSM are proprietary to and distributed by Dow Jones & Company, Inc. and have been licensed for use. All content of the Dow Jones IndexesSM © 2014 is proprietary to Dow Jones & Company, Inc. Chicago Mercantile Association. The market data is the property of Chicago Mercantile Exchange Inc. and its licensors. All rights reserved. FactSet Research Systems Inc. 2014. All rights reserved. Most stock quote data provided by BATS.