The Observer was first published in New York City on September 22, 1987, as a weekly alternative newspaper by Arthur L. Carter, a former investment banker.

The New York Observer had also been the title of an earlier weekly religious paper founded 164 years before by Sidney E. Morse in 1823.

Previous prominent writers for the publication include Joe Conason, Doree Shafrir, Hilton Kramer, Andrew Sarris, Richard Brookhiser, Michael Tomasky, Azi Paybarah, Ross Barkan, John Heilpern, Robert Gottlieb, Nicholas von Hoffman, Simon Doonan, Anne Roiphe, Terry Golway, Ron Rosenbaum, Michael M. Thomas, Philip Weiss, and Steve Kornacki.

It was visually distinctive because of its use of sketch illustrations and salmon-colored newsprint, with the latter compared to the similar physical appearance of the Financial Times from Britain.

In January 2013, publisher Jared Kushner named his longtime friend Ken Kurson, a political consultant, journalist, and author, as the Observer's next editor.

Kushner transferred his ownership of Observer Media's remaining online assets into a Trump family trust, through which his brother-in-law Joseph Meyer took over his former role as publisher during that time.

[14] Defunct Newspapers Journals TV channels Websites Other Congressional caucuses Economics Gun rights Identity politics Nativist Religion Watchdog groups Youth/student groups Miscellaneous Other In 2016, the Observer became one of a handful of newspapers to officially endorse United States presidential candidate Donald Trump in the Republican Party presidential primaries.