Joseph Medill, a native Ohioan who acquired an interest in the Tribune in 1855, gained full control of the newspaper in 1874 and ran it until his death in 1899.

[6] To compete with the Saturday Evening Post and Collier's in 1924, the Tribune Company launched a weekly national magazine, Liberty, run by a subsidiary, McCormick-Patterson.

Expecting a printer's strike in November 1948, the Tribune printed their paper early, mistakenly proclaiming "Dewey Defeats Truman" in the 1948 presidential election.

Tribune entered the television industry then in its infancy, in 1948, with the establishment of WGN-TV in Chicago in April and WPIX in New York City in June of that year.

In August of that year, Tribune purchased the Chicago Cubs Major League Baseball team from William Wrigley III.

In 1985, Tribune Broadcasting acquired Los Angeles independent station KTLA from Kohlberg Kravis Roberts for a record $510 million.

Because of the Federal Communications Commission's media cross-ownership regulations, which prohibit the ownership of a television station and newspaper in the same market, Tribune was forced to sell the Los Angeles Daily News.

With the purchase of KTLA, Tribune became the fourth largest television station owner in the United States, behind the three major broadcast networks.

[6] With changes in the media industry due to greater public access to the internet in the 1990s, Tribune Publishing began to sell off some of its newspaper properties.

[6] In June 1998, Tribune entered into a trade with Emmis Communications to swap WQCD-FM to the latter company, in exchange for acquiring two Emmis-owned television stations (WXMI in Grand Rapids, Michigan and KTZZ in Seattle, Washington).

Later that year, the station purchased WEWB in Albany, New York and WBDC in Washington, D.C. Tribune Interactive, Inc. was incorporated to handle all the various websites for its publishing, television and radio, and newspaper properties.

In February 2000, Tribune acquired the remaining 67% interest in Qwest Broadcasting for $107 million, effectively adding two more stations to its roster, increasing its reach 27% of the country.

Hoy, a Spanish language newspaper owned by the company, expanded with the launch of local editions in Chicago (in September 2003) and Los Angeles (in March 2004).

[6] That same year, Tribune pushed for the FCC to loosen its regulations barring cross-ownership of newspapers and broadcast outlets (television and/or radio) in a single market.

Tribune would have to sell either a newspaper or television station in Los Angeles, New York City and Hartford while its combination of the Sun-Sentinel and WBZL-TV in Miami/Fort Lauderdale, Florida was given a temporary waiver.

[14] On January 31, 2008, Tribune Company announced it would purchase real estate leased from TMCT, LLC, which included properties used by the Los Angeles Times, Newsday, Baltimore Sun and Hartford Courant.

The parties also agreed to a five-year lease allowing its television station in the city, KTLA, to continue operating at the location through 2012.

On December 8, 2008, faced with a high debt load related to the company's privatization and a sharp downturn in newspaper advertising revenue, Tribune filed for Chapter 11 bankruptcy protection.

The sale also included Wrigley Field and a 25% ownership stake in Comcast SportsNet Chicago, as part of a deal designed to help Tribune restructure.

[21] In October 2010, Randy Michaels, who was appointed CEO after Zell's purchase of the company, was removed and replaced by an executive council.

The New York Times had reported earlier in the month about his "outlandish, often sexual behavior" that he also exercised in his previous job at Clear Channel Communications.

[27] On July 1, 2013, Tribune announced that it would purchase the 19 television stations owned by Local TV, LLC outright for $2.75 billion.

[32] The split came in the footsteps of similar spin-outs by News Corporation and Time Warner, which sought to improve the profitability of their properties by separating them from the struggling print industry.

[42] On April 20, 2017, Bloomberg reported that Sinclair Broadcast Group was considering acquiring Tribune Media, contingent on plans by the FCC's new chairman, Ajit Pai, to reinstate the "UHF discount" (a policy which makes UHF stations only count half of their total audience towards the FCC's 39% market share cap), which had been removed by Tom Wheeler during the final months of the Obama administration.

[45][46][47][48] The Fox/Blackstone deal was being proposed as a defensive measure, due to concerns by 21st Century Fox over the number of Fox-affiliated stations Sinclair would control if it acquired Tribune Media.

[53] The proposed sale resulted in concerns from various groups over the effects of the UHF discount on U.S. media; the Institute for Public Representation coalition filed a request for an emergency motion to stay the reinstatement of the UHF discount order pending a court challenge, echoing Wheeler's opinion that it was outdated and intended to trigger media consolidation.

[62] On that same date, another Tribune Media shareholder, identified in legal paperwork as Robert Berg, also filed a class-action lawsuit.

Additionally, the registration statement allegedly omits information about potential conflicts of interest concerning Tribune's board of directors and one of its financial advisors.

Berg further claims that stockholders are entitled to "an accurate description" of the background of the deal, including processes used by the board to arrive at their decision to recommend the merger.

[66][67][68][69][70] On July 16, 2018, FCC chairman Ajit Pai was reported to have "serious concerns" about the merger and proposed a hearing before an administrative law judge.