In this series, we take a look at the 25 stocks on the S&P 500 Index (SPX) that have turned in the worst performance during the past decade -- what went wrong, and what happens next.

Permit me, if you will, to draw up an analogy: Qwest Communications (NYSE: Q) is to Wall Street as Lindsay Lohan is to Hollywood. At first, the little redheaded upstart seems to come out of nowhere, and dazzles everyone with her amazing performance. Then, just as quickly as the newcomer rose to fame, she sinks into a massive meltdown, the scope and severity of which is shocking even to seasoned vets. Okay, so this little comparison probably won't find its way onto the SATs, but -- minus the "redheaded" part -- the similarities are kind of eerie.

What went wrong? At lucky number 13 on our list of SPX underperformers, Q shed 77% of its value during the decade that ended on June 30, 2008. The shares peaked at $66 in March 2000, and bottomed out at $1.02 in August 2002 - a 98.5% plunge, top to bottom.

When Colorado-based Qwest burst onto the Big Board in June 1997, it was a company with a vendetta. CEO Joseph Nacchio defected from his executive position at AT&T (NYSE: T) after it became clear that Ma Bell didn't see him as president material. Qwest was in the process of building a massive fiber-optic network, and the upstart was determined to grab market share away from the industry's old giants -- including AT&T, naturally.

In early 1998, the company's acquisition of LCI International made Q the fourth-largest long-distance carrier in the U.S. Later that year, Qwest announced a partnership with Netscape Communications, which was then the major player in web browsing. Even more satisfying, Nacchio hired Jack McMaster away from AT&T to head up Qwest's international operations. By the end of '98, Microsoft (NASDAQ: MSFT) announced plans to invest $200 million in Qwest, with a quid pro quo arrangement for Qwest to develop internet applications based on Windows NT.

By June 1999, though, Qwest's long honeymoon on Wall Street was nearing its end. The company's hostile, $55-billion bid to acquire U S West Inc. and the Frontier Corporation was met with both confusion and disappointment from shareholders. The move was primarily a defensive one: competitor Global Crossing was angling to acquire both firms for $47 billion. Eventually, after weeks of maneuvering, Qwest and Global Crossing agreed to split the pot -- the former would merge with U S West, and the latter's consolation prize was Frontier.

Unfortunately, the pending merger with U S West eventually dashed Qwest's chance to be acquired by Deutsche Telekom. And, in November 2000, Q lost a major moral battle -- a Texas judge ordered Qwest to pay AT&T more than $350 million in punitive damages for negligently cutting one of Ma Bell's fiber optic phone lines. By November 2001, a cash-strapped Qwest posted an unexpected third-quarter loss, and instructed contractors to halt construction on its fiber-optic network.

Several months later, investors would learn that Qwest struck a hasty bargain with on-the-verge Enron toward the end of that fateful quarter. The struggling companies agreed to swap fiber-optic network capacity and services at inflated prices in order to artificially boost both of their balance sheets. In a word, yikes.

After eight consecutive unprofitable quarters, Nacchio was unceremoniously ousted from his CEO post in June 2002. In 2007, the brash ex-CEO was convicted on 19 out of 42 counts of insider trading; this past March, a federal appeals court panel reversed the conviction and ordered a new trial due to the exclusion of an expert witness in the original proceedings.

What next? While the stock's price action is not as wildly volatile as it once was, Qwest continues to struggle. The shares have trended lower since June 2007, with resistance looming overhead from their 10-week and 20-week moving averages. Meanwhile, most analysts expect the stock to double during the next year -- Thomson Financial reports that the average 12-month price target on Q is $6.15. The stock has already proven itself capable of quick, impressive growth ... but can Qwest outperform on the up-and-up?

Elizabeth Harrow is an analyst and financial writer in the research department at Schaeffer's Investment Research. She is featured in the weekly video series Option Basics on SchaeffersResearch.com.