The Las Vegas Sun is its city's second longest published newspaper, with a legendary past as a muckraker and crusader. It debuted on May 3, 1950, as the Las Vegas Free Press, a thrice-weekly newspaper founded by the International Typographical Union, which consisted of typesetters locked out of the Las Vegas Review-Journal for trying to unionize.

Despite the presence of longtime Review-Journal editors Sherwin Garside and Ray Germain, who also were partners in a local printing company, the Free Press was in trouble, with advertisers shying away from it, except for the Desert Inn's director of publicity, Hank Greenspun. Greenspun's crusading instincts and his unhappy relationship with Desert Inn operator Moe Dalitz prompted him to buy the Free Press, expand it to five days a week, and rename it the Las Vegas Sun, as of July 1, 1950. He remained publisher and, except for the brief tenure of longtime aide Adam Yacenda, editor until his death in 1989.

Greenspun's front-page "Where I Stand" column featured what he called his "primitive, pungent and unpredictable prose." He attacked U.S. Senator Pat McCarran, whom he accused of being a corrupt political boss; U.S. Senator Joseph McCarthy, whom he assailed as a bully and liar; and the Review-Journal, which he called a "toady" for the two senators. Greenspun also blasted the gaming industry for its ties to organized crime. The Sun weathered a 1952 advertising boycott engineered by McCarran and the casino owners, with Greenspun winning not only a federal court settlement against them, but his indictment in 1954 for allegedly inciting McCarthy's assassination (he was easily acquitted).

The Sun nearly caught the R-J in advertising and circulation, thanks in part to its fresher news coverage which targeted the more entrenched Review-Journal sacred cows. The older daily began pulling ahead in the early 1960s, and a fire that destroyed the Sun building in November 1963 made the R-J's lead insurmountable. Greenspun kept publishing and printing in Los Angeles until a new plant was complete.

The Sun wound up bathed in red ink despite many significant advantages: Greenspun's political and financial power; the involvement of family members like his wife Barbara, his son Brian, and his in-laws; the efforts of such key figures as Ruthe Deskin, who became his assistant in 1954 and remained with the Sun until her death in 2004; Bryn Armstrong, managing editor from 1962 to 1977; and Mike O'Callaghan, who became an editor and a columnist upon leaving the governor's office in 1979. O'Callaghan remained a political and journalistic force until his death in 2004.

The Sun also faced criticism precisely for employing so many members of Greenspun's family, as well as longtime columnists and reporters seen as doing his bidding or acting in their own interests. It also developed a reputation for treating Greenspun's friends and allies, most notably Horseshoe boss Benny Binion, with kid gloves and attacking those he fought politically or financially. For Greenspun and writers like news columnist Paul Price and entertainment commentator Ralph Pearl, the Sun also was distinctive and personal, in comparison with the R-J and other newspapers that belonged to more homogenized chains.

The chain proved far more successful in the changing Las Vegas market. By the time Greenspun died in 1989, the R-J almost totally dominated the region. While he was dying, Greenspun approved his family's negotiation of a Joint Operating Agreement with the Review-Journal. When it was completed the next year, the Greenspuns owned ten percent of the combined operation. The R-J completely controlled the business side while the Sun maintained its editorial independence in weekday afternoon editions and sections published inside the R-J on weekends and holidays.

The Sun also maintained its distinctive journalistic voice, thanks to columnists such as Deskin; O'Callaghan; longtime reporter Jeff German; editor and columnist Sandy Thompson, who made the problems and operations of family court her crusade until her death in an auto accident in 2002; Thompson's husband, veteran gaming reporter and managing editor Gary Thompson, who left the paper to handle publicity for Harrah's; and reporters such as Mary Manning, who covered nuclear issues, and Ed Koch, who wrote extensive obituaries on longtime Las Vegans.

By 2005, the Sun's circulation in the afternoon, a largely dying market for newspapers, was less than twenty-eight thousand. Its influence rested on its history and the significance of Brian Greenspun, who followed in his father's footsteps as a developer and political figure. The Sun also took advantage of a new opportunity to influence Las Vegans. Given its declining circulation, the Greenspuns and the Review-Journal negotiated a change in the Joint Operating Agreement. As of September 30, 2005, the Sun would appear as a six-to ten-page section each morning in the R-J. While it no longer appeared as a separate publication, its stories, columns, and features now would reach more than 160,000 subscribers.