In 1956, Bil Dunaway, a U.S. Army 10th Mountain Division veteran, bought The Aspen Times, and over the next 35 years would amass a local media empire. At one time, he owned KSNO-AM 1260, Aspen's cable TV company and its only newspaper. Downvalley, he also owned Glenwood Springs, Colorado radio station KMTS-FM 99.1, the Valley Journal in Carbondale, Colorado, The Rifle Telegram and Climbing magazine. Dunaway was a crusading newspaper editor as well as a world-class ski racer and a prolific mountainer.
In 1990, Price covered the arrest of gonzo journalist Hunter S. Thompson on sex assault charges. The charges were dropped after Price reported that the alleged victim was an undercover agent who fabricated the assault claim in order to give the district attorney a pretext for searching Thompson's Woody Creek ranch for drugs. Thompson reprinted some of Price's stories in his 1990 book "Gonzo Papers, Vol. 3: Songs of the Doomed: More Notes on the Death of the American Dream."
In 1992, Dunaway sold the Times to a group led by Loren Jenkins, a Pulitzer Prize-winning reporter for the Washington Post. Jenkins improved the newspaper by redesigning it and bringing in national and international news and cultural reporting and reviews from the services of the New York Times and the Washington Post. He also gave the newspaper an editorial edge that sought to slow down rampant development and preserve the local values and nature that had always made the Roaring Fork valley special. Jenkins left town in 1996, taking the post of foreign desk editor at National Public Radio.
In 1995, the ownership of the paper changed again, and this time the group included as many as nine investors by some reports. Among them were local businessmen George Stranahan, Michael McVoy and longtime Times writer and novelist Andy Stone.
On December 1, 1999, the Times was sold to its current owner, Swift Newspapers of Reno, Nevada. Swift stopped printing the paper in Aspen when it opened a new press facility in Gypsum, Colorado, on I-70.
The Aspen Times printed both weekly and daily editions until 2004, when the weekly was converted into a Sunday edition. At that point, the Times Daily went from Monday-Friday to seven days a week. The word "Daily" was dropped from the title of the daily paper in the 1990s.
In 2005, Swift purchased the Aspen Times building at 310 E. Main St. from Dunaway for $2.3 million. The Times moved into the building, which is next door to the historic Hotel Jerome, in 1905.