Joseph Nacchio, the former boss of Qwest Communications, has been sentenced to six years in jail for insider trading.
He has also been ordered to hand over the $52m (£25m) he made from illegal stock trading and has been fined $19m.
Nacchio was found guilty of selling shares ahead of bad corporate news, and hiding information from investors.
Thousands of shareholders lost money as Qwest's share price slumped from $60 in 2000 to $2 in 2002.
"The crimes the defendant has been found guilty of are crimes of overarching greed," said US District Judge Edward Nottingham.
Nacchio's lawyers have said that they would appeal the ruling, though the judge earlier dismissed calls for a retrial.
Nacchio is the latest boss of a large US firm to be jailed as prosecutors clamp down on corporate misdeeds following the collapse of energy trading firm Enron in 2001 and telecommunications provider WorldCom in 2002.
Former Enron boss Jeffrey Skilling was jailed last year for 24 years, and former WorldCom chief Bernard Ebbers was given a 25 year sentence.
Qwest, the third-largest US regional phone company, became the target of both prosecutors and regulators in 2002, after it restated £2.2bn in revenues.
In April, Nacchio was found guilty of 19 counts of insider trading. He was acquitted on 23 counts.
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