A newspaper has been in existence in some form in the city of Middletown since 1851. The
Times Herald was the result of a 1927 merger of the
Times-Press, a merger of the old Middletown
(Whig) Press of the 1850s and the
Daily Times, founded in 1891, and the
Daily Herald, founded in 1918, but also going back to the 1850s. The
Times Herald had the Middletown market to itself from 1927 until 1956, when Jacob M. Kaplan started publishing the
Middletown Daily Record, the first daily U.S. newspaper to use
cold type, from a garage on North Street. The new paper grew to a daily
circulation of 19,000 within three years but lost a lot of money in the process. In November 1959, James H. Ottaway Sr., the founder of Ottaway Newspapers Inc., bought the
Times-Herald and the
Port Jervis Union-Gazette from
Ralph Ingersoll, who had owned the papers since 1951.
The Gazette, serving Port Jervis and surrounding communities, still exists as a weekly newspaper published by the
Times Herald-Record. A few months later, in April 1960, Kaplan sold his
Daily Record to Ottaway. On September 4, 2013,
News Corp announced that it would sell the Dow Jones Local Media Group to Newcastle Investment Corp.—an affiliate of
Fortress Investment Group, for $87 million. The newspapers were to be operated by
GateHouse Media, a newspaper group owned by Fortress. News Corp CEO and former
Wall Street Journal editor
Robert James Thomson indicated that the newspapers were "not strategically consistent with the emerging portfolio" of the company. GateHouse in turn filed prepackaged Chapter 11 bankruptcy on September 27, 2013, to restructure its debt obligations in order to accommodate the acquisition. GateHouse was subsequently purchased by
New Media Investment Group in 2019 and merged into
Gannett, making Gannett the largest newspaper chain in the United States with over 100 dailies. In February 2020, the paper announced it would be closing its printing plant in
Wallkill, New York and outsourcing its printing to a plant in
Rockaway, New Jersey in order to "adapt to market-driven changes and competition." Ninety-four employees were laid off in the process. In July 2021, employees of the
Times Herald-Record,
Poughkeepsie Journal and
The Journal News voted to unionize. They joined the
NewsGuild-CWA and formed the Hudson Valley News Guild. In February 2024, the newspaper announced it would switch from carrier to postal delivery. ==Prominent employees==