He was the last top former official to be punished for the accounting tricks and shady business deals that led to the loss of thousands of jobs, more than $60 billion in Enron stock and more than $2 billion in employee pension plans when Enron collapsed.
Skilling's term is the longest received by any Enron defendant; former chief financial officer Andrew Fastow was given a six-year term after cooperating with prosecutors and helping them secure Skilling's conviction.
The former CEO's arrogance, belligerence and lack of contriteness under questioning made him a lightning rod for the rage generated by the collapse of Enron in 2001.
Before he was sentenced, Skilling told the judge that he's innocent – but that he does have some remorse. He said the Enron collapse had been "very hard" on him, as well as on his family and friends, the community and Enron employees.
"He certainly didn't help himself when he stood up in front of the judge and declared his innocence once again," says CBS News legal analyst Andrew Cohen. "That's not what sentencing judges are looking for — they are looking from defendants for genuine and humble expressions of regret and an acknowledgement of responsibility, and Skilling gave his trial judge neither of those things."
Skilling was convicted in May on 19 counts of fraud, conspiracy, insider trading and lying to auditors. He was acquitted on nine counts of insider trading.
His co-defendant, Enron founder Kenneth Lay, died from heart disease on July 5. Lay's convictions on 10 counts of fraud, conspiracy and lying to banks in two separate cases were wiped out with his death.
Jurors decided Skilling and Lay repeatedly lied about Enron's financial health when they knew an illusion of success was propped up by accounting maneuvers that hid debt and inflated profits.
In the end it came down both to Skilling's role in the fraud that rotted out the company's core, and the nature and extent of the financial damage itself, which was colossal by any measure, says Cohen.
Enron's crash and the subsequent scandals roiled Wall Street, sent investors fleeing, prompted stiffened white collar penalties and upped regulatory scrutiny over publicly traded companies
Skilling, 52, maintained his innocence before, during and even after his trial, insisting no fraud occurred at Enron other than that committed by a few executives skimming millions in secret side deals, and that bad press and poor market confidence combined to sink the company.
Under federal sentencing guidelines, which Lake has said he will rely on, Skilling faces more than 20 years in prison if investor loss tied to his actions exceeds $80 million. Skilling also faces more than $18 million in fines for his crimes.
Prosecutors and Skilling's attorneys have agreed on an investor loss figure, but it is in sealed court documents and none of the lawyers would discuss it.
"Now the appeal can begin for real and Skilling has some decent arguments to make," says Cohen. "For example, his attorneys are going to argue that the trial judge gave jurors the wrong instructions before they began to deliberate and improperly allowed jurors to see and hear certain evidence they weren't supposed to."
Skilling never endeared himself to co-workers, or even the city, the way Lay had with his affable demeanor and charity work.
Since his indictment, Skilling has had two run-ins with the law for public drunkenness.
Skilling has asked that he be allowed to remain free on bail pending his appeals in the case. Lake will rule on that request Monday.
Prosecutors have also asked that Skilling turn over nearly $183 million, which they claim he pocketed while at Enron. The U.S. government had divided that amount between Skilling and Lay. But Lay's death has left that amount solely on Skilling.
The government contends about $60 million in Skilling's cash and property that has been frozen since his indictment could be applied to the total amount they are seeking.
Skilling, who was born in Pittsburgh and raised in New Jersey and suburban Chicago, spent 11 years at Enron.
He took over as chief executive from Lay in February 2001 but abruptly quit six months later, citing a desire to spend more time with his family. Prosecutors said he left Enron because he knew the company was on the brink of bankruptcy.