In his haste to attain greatness, Nacchio committed a few tactical blunders -- including erratic M&A maneuvers that left shareholders uneasy. The icing on the felonious cake, though, came in 2001, when Qwest struck a deal with Enron (yes, that Enron). Both companies were facing the prospect of ugly earnings reports, and so the enterprising duo agreed to swap fiber optic network capacity for services in a deal valued at $500 million.

By this time in U.S. history, the telecom bubble had already sprung a terminal leak, and the market was choking on a glut of fiber optic capacity. As such, the Qwest deal raised a few eyebrows when it came to light, months after the fact, during the course of Enron's bankruptcy proceedings. The New York Times reported in March 2002 that company executives, including Nacchio and Enron chief Jeffrey K. Skilling, "ponder[ed] how to account for the deal so that each would gain accounting benefits and improve its quarterly earnings report." Just a few months later, Nacchio was going by the title of "ex-CEO of Qwest."

And so, in April 2007, the hard-charging exec was convicted of 19 counts of insider trading, and acquitted of 23 more. (Apparently, the government used to prosecute unethical CEOs who engaged in fraudulent behavior.) It was a moral victory for the citizens of Denver; the Washington Post observed that Nacchio's colossal mismanagement of Qwest cost the city "thousands of jobs and millions of dollars in retirement savings."

However, Nacchio's propensity for finding trouble just might be matched by his ability to dodge the consequences. Denver's 10th Circuit Court of Appeals overturned his conviction in March 2008 after finding that the exclusion of testimony by expert witness Daniel Fischel unfairly skewed the case. One dissenting judge argued that the omission of Fischel's remarks was the failure of Nacchio's own defense team, and the conviction should stand.

In an interesting turn of events, it appears that Nacchio's extreme case of hubris might be communicable. Edward Nottingham, who presided over the ex-CEO's insider trading trial, stepped down from the bench in October after a number of complaints were lodged against him. The former Chief Judge of the 10th Circuit is accused of soliciting prostitutes, using a court-owned cell phone to call said prostitutes, asking the aforementioned prostitutes to lie to federal investigators, and improperly parking in handicapped spaces. Nottingham is now the subject of a criminal investigation by the U.S. Department of Justice.

Elizabeth Harrow is an analyst and financial writer in the research department at Schaeffer's Investment Research. She is featured in the video series Schaeffer's Daily Q&A on SchaeffersResearch.com.