Jeffrey Keith Skilling was born in Pittsburgh, Pennsylvania, on November 25, 1953, the second of four children of Betty (née Clarke) and Thomas Ethelbert Skilling, Jr. His father was a sales manager for an Illinois valve company. His older brother, Tom Skilling, later became chief meteorologist at WGN-TV. Skilling grew up between New Jersey and Aurora, Illinois. When he was 16 years old, he worked at WLXT-TV (channel 60), a UHF television station in Aurora. He graduated from West Aurora High School and received a full scholarship to Southern Methodist University in Dallas, Texas, where he was a member of the Beta Theta Pi fraternity.

Skilling initially studied engineering before changing to business. After graduating in 1975, he went to work as a corporate planner for First City Bancorporation of Houston, Texas. He quit by 1977 to attend Harvard Business School. According to Skilling, during his admissions interview for Harvard Business School, he was asked if he was smart, to which he replied, “I’m fucking smart.” This apparently so impressed the interviewer that it secured his place at the school. He earned his MBA from Harvard Business School in 1979, graduating in the top 5% of his class as a Baker Scholar.

As a consultant for McKinsey & Company, Skilling worked with Enron during 1987, helping the company create a forward market in natural gas. Skilling impressed Kenneth Lay in his capacity as a consultant, and was hired by Lay during 1990 as chairman and chief executive officer of Enron Finance Corp. In 1991, he became the chairman of Enron Gas Services Co., which was a result of the merger of Enron Gas Marketing and Enron Finance Corp. Skilling was named CEO and managing director of Enron Capital and Trade Resources, which was the subsidiary responsible for energy trading and marketing. He was promoted to president and chief operating officer of Enron during 1997, second only to Lay, while remaining the manager of Enron Capital and Trade Resources.

Skilling has a daughter and two sons from his first marriage to Susan Long, which ended in divorce in 1997. His youngest child, John Taylor “JT” Skilling, was found dead from a drug overdose at age 20 in his apartment in Santa Ana, California on February 3, 2011.

During Skilling’s management, Enron adopted “mark-to-market” accounting, in which anticipated future profits from any deal were accounted for by estimating their present value rather than historical cost. Skilling began advocating a novel idea: by promoting the company’s aggressive investment strategy, the company didn’t really need any “assets”. This plan helped make Enron the largest wholesaler of gas and electricity, with $27 billion traded in a quarter. On February 12, 2001, Skilling was named CEO of Enron, replacing Lay. He received $132 million during a single year. Skilling was slated to succeed Lay as chairman as well in early 2002.

On March 28, 2001, PBS’s Frontline interviewed Skilling, where he claimed for Enron “We are the good guys. We are on the side of angels”.

On April 17, 2001, Skilling made what became an infamous comment during a conference call with financial analysts. In response to fund manager Richard Grubman saying “You know, you are the only financial institution that can’t produce a balance sheet or cash flow statement with their earnings”, Skilling replied: “Thank you very much, we appreciate that… asshole.”

In March 2002, Skilling married Rebecca Carter, a former vice president for board communications and board secretary at Enron.

Skilling was indicted on 35 counts of fraud, insider trading, and other crimes related to the Enron scandal. He surrendered to the Federal Bureau of Investigation on February 19, 2004, and pleaded not guilty to all charges. The indictments emphasized his probable knowledge of, and likely direct involvement with, the fraudulent transactions within Enron. About a month after quitting Enron, Skilling sold almost US$60 million of his stake in the company (in blocks of 10,000 to 500,000 shares), resulting in the prosecutors’ allegation that he sold those shares with inside information of Enron’s impending bankruptcy. Skilling’s main attorney was Daniel Petrocelli, the 52-year-old civil litigator who represented Ron Goldman’s father in his successful civil suit against O. J. Simpson for negligent death. Skilling spent $40 million in preparation for the trial, of which at least $23 million went to his defense lawyers’ retainer. Skilling’s younger brother Mark is an attorney and assisted his legal team during the criminal trial.

In April 2004, Skilling got into a scuffle with patrons of a cigar bar in New York City after a night of drinking. He was not arrested, but he and his wife, Rebecca, who was hurt during the scuffle, were transported to a hospital where a blood test showed Skilling had a blood-alcohol level of 190 milligrams per decaliter (0.19% BAC), as indicated in the government’s motion to modify conditions of Skilling’s pretrial release order. Prosecutors moved against Skilling, asking a judge to increase his $5 million bond to $7 million, restrict his travel to Texas and impose a curfew. They argued that Skilling violated his bond’s terms by drinking excessively and failing to report his contact with police to federal pretrial services authorities.

The Securities and Exchange Commission had sued Skilling for his misdeeds in February 2004, around the time that the criminal case was brought. The SEC case was stayed, however, pending resolution of the criminal case. On December 8, 2015, federal judge Melinda Harmon granted summary judgment to the SEC and permanently barred Skilling from serving as an officer or director of a public company.

The trial began on January 30, 2006, in Houston, despite repeated protests from defense attorneys calling for a change in venue on the grounds that “it was impossible to get a fair trial in Houston”. Skilling, known for his harsh attitude and arrogance, lost his temper on the witness stand during the trial. Enron’s bankruptcy, the largest in U.S. history when it was filed during December 2001, cost 20,000 employees their jobs. In addition, many of them lost their life savings. Investors also lost billions. Skilling and many of the company’s executives had sold huge portions of their own Enron stock before the bankruptcy filing, making a substantial profit. On May 25, 2006, the jury returned with the following findings regarding Skilling:

In a front-page interview with The Wall Street Journal on June 17, 2006, Skilling claimed that he had been melancholic after the Enron bankruptcy and that he had considered suicide, but that his indictment actually ended his depression. He also claimed that the worst witness against him was himself, and that he would be able to survive a long prison term as long as he is given “something to do, something to accomplish” while in prison.

On October 23, 2006, Skilling was sentenced to 24 years and four months in prison, and was fined US$45,000,000 (equivalent to $57,070,815 in 2019). All of his convictions save one were ultimately upheld on appeal, as was his sentence. Skilling’s request to remain free during appeal was denied by Judge Patrick Higginbotham of the Fifth Circuit Court of Appeals on December 12, 2006. In ordering Skilling’s immediate imprisonment, the judge wrote, “Skilling raises no substantial question that is likely to result in the reversal of his convictions on all of the charged counts,” although the order also noted “serious frailties” were possible in some (but not all) of the convictions.

Skilling began his sentence on December 13, 2006, and was housed at the Montgomery Federal Prison Camp, Maxwell Air Force Base, Montgomery, Alabama until 2018. According to the Federal Bureau of Prisons, he was scheduled for release on February 21, 2019, but on August 30, 2018 Skilling was released from prison and sent to a halfway house in Texas to serve out his prison sentence.

On April 3, 2008, Skilling’s defense attorney, Daniel M. Petrocelli, argued with government prosecutors that Skilling’s trial and the conviction itself was based on honest services fraud, which he said did not apply to Skilling. This argument was based on the idea that, even though Skilling committed illegal financial maneuvers, he did so in order to save the company and did not profit from it. This was cited as a possible basis for overturning some or all of his convictions; however, the chances of this were considered to be very narrow.

On October 30, 2008, Skilling was moved to a low-security prison near Littleton, Colorado, as his original prison, FCI Waseca, was being converted to an all-female facility.

On October 13, 2009, the Supreme Court of the United States agreed to hear two questions presented by Skilling’s appeal. The Court subsequently scheduled and heard argument March 1, 2010.

On June 24, 2010, in an opinion by Justice Ruth Bader Ginsburg, the Supreme Court unanimously nullified Skilling’s honest services fraud conviction, finding that “Skilling’s misconduct entailed no bribe or kickback”. The Court remanded the Skilling case back to the lower court for further proceedings to decide which charges must now be dismissed as the result of the invalidation of the honest services statute.

In April 2011, a three-judge panel of the Fifth Circuit Court of Appeals ruled that since the jury was presented with “overwhelming evidence” that Skilling conspired to commit conspiracy fraud, the verdict would have been the same even if the honest services theory had never been presented, and Skilling’s conviction was confirmed. The case in the Fifth Circuit is United States of America v. Jeffrey K. Skilling, 06-20885. Skilling appealed this new decision to the Supreme Court, but was denied certiorari. In 2013, Skilling’s lawyers and the Justice Department reached a deal that called for Skilling’s sentence to be reduced to 14 years. Federal judge Simeon T. Lake III, who had presided over Skilling’s 2006 trial, accepted the deal on June 21, 2013.

Skilling was released from federal custody on February 21, 2019.