The Sentinel's predecessors date to 1876, when the Orange County Reporter was first published. The Reporter became a daily newspaper in 1905, and merged with the Orlando Evening Star in 1906. Another Orlando paper, the South Florida Sentinel, started publishing as a morning daily in 1913. Then known as the Morning Sentinel, it bought the Reporter-Star in 1931, when Martin Andersen came to Orlando to manage both papers. Andersen eventually bought both papers outright in 1945, selling them to the Tribune Company of Chicago in 1965.
In 1973, the two publications merged into the daily Sentinel Star. Tribune appointed Charles T. Brumback as president in 1976. Harold "Tip" Lifvendahl was named president and publisher in 1981. The newspaper was renamed the Orlando Sentinel in 1982. John Puerner succeeded Lifvendahl in 1993, who was replaced by Kathleen M. Waltz in 2000. She announced her resignation in February 2008. Howard Greenberg, already publisher of fellow Tribune newspaper the Sun-Sentinel of Fort Lauderdale, was named publisher of both papers after Waltz left.
In 2008, the Tribune Company called for a redesign of the Sentinel. The new layout, which debuted in June 2008, was formatted to appeal to busy readers, though like all of the redesigns in Tribune's Sam Zell ownership era, was reeled back into a more traditional design with appealing elements kept after reader criticism.
According to one listing, some of the Sentinel's predecessors are:
- Orlando Reporter: 1892–1903? (merged with Evening Star to form Evening Reporter-Star)
- Evening Star: January–December 1903? (merged with Orlando Reporter to form Evening Reporter-Star)
- Evening Reporter-Star: 1904?–March 1947 (continues Orlando Reporter and Evening Star; continued by Orlando Evening Star)
- Orlando Evening Star: April 1947 – 1973 (continues Evening Reporter-Star; merged with Orlando Morning Sentinel to form the Orlando Sentinel-Star)
- Orlando Morning Sentinel: 1913–1973 (title varies: Daily Sentinel; Morning Sentinel; merged with Orlando Evening Star to form the Orlando Sentinel-Star)
- Orlando Sentinel-Star: 1974–April 25, 1982 (continues Orlando Morning Sentinel and Orlando Evening Star; continued by Orlando Sentinel)
- Orlando Sentinel: April 26, 1982–present (continues Orlando Sentinel-Star)
Editorially, the Sentinel has historically tilted conservative; however, it has endorsed Democratic candidates for president in three of the last four presidential elections: John Kerry in 2004, Barack Obama in 2008, and Hillary Clinton in 2016.
In June 2019, the day of President Donald Trump's re-election campaign launch rally in Orlando, the Sentinel made national news when the editorial board published a piece saying it would not endorse the president, among their reasons, "the chaos, the division, the schoolyard insults, the self-aggrandizement, the corruption, and especially the lies."
- 1982: Gerald Loeb Award Honorable Mention for Small Newspapers for "The Federal Impact Series"
- 1988: editorial writing, Jane Healy, "for her series of editorials protesting overdevelopment of Florida's Orange County."
- 1993: investigative reporting, Jeff Brazil and Steve Berry, "for exposing the unjust seizure of millions of dollars from motorists—most of them minorities—by a sheriff's drug squad."
- 2000: editorial writing, John C. Bersia, "for his passionate editorial campaign attacking predatory lending practices in the state, which prompted changes in local lending regulations."
- Michael A. Bianchi: sports columnist
- Jane Healy, first Sentinel journalist to receive a Pulitzer Prize
- El Sentinel (Orlando)
- El Sentinel del Sur de la Florida
- South Florida Sun-Sentinel
- Tribune Company
- Tribune Publishing
- Tronc, Inc. (2016), 2016 Annual Report, Chicago, Illinois, archived from the original on 2017-10-27, retrieved 2017-03-26
- "About - Orlando Sentinel". orlandosentinel.com. Retrieved 2019-06-26.
- "Tribune Publishing Public Filing FORM 10-12B/A" (PDF). 2014-07-21. p. 97. Retrieved 2014-07-21.
- "History Of The Orlando Sentinel".
- Rene Stutzman (July 30, 1993). "Lifvendahl To Tribune Senior Vp". Orlando Sentinel. Retrieved May 26, 2014.
- Rene Stutzman (October 4, 1993). "New Era At Sentinel". Orlando Sentinel. Retrieved May 26, 2014.
- Suzanne White (May 27, 2000). "Waltz Moving To Orlando Sentinel". Daily Press. Retrieved May 26, 2014.
- Christopher Boyd (February 15, 2008). "Orlando Sentinel's publisher resigns". Orlando Sentinel. Retrieved October 25, 2011.
- "Tribune’s Redesign Kicks Off With Orlando Sentinel"
- "US: Orlando Sentinel redesign geared towards "busy readers""
- See Florida Newspapers—a list of Florida newspapers for which indexes or full-text are available at the University of Central Florida Library.
- Bennett, Dashiell (2012-10-19). "Orlando Sentinel Backs Romney After Endorsing Obama in 2008". The Atlantic. Retrieved 2019-10-10.
- "Orlando Sentinel endorses Marco Rubio, Hillary Clinton for nominations". WGNO. 2016-03-06. Retrieved 2019-10-10.
- Forgey, Quint. "Orlando Sentinel announces 2020 endorsement: Not Trump". POLITICO. Retrieved 2019-06-19.
- "Orlando Sentinel newspaper makes 'not Trump' anti-endorsement". MSNBC.com. Retrieved 2019-06-19.
- Klar, Rebecca (2019-06-18). "Orlando Sentinel declines to endorse Trump in 2020". TheHill. Retrieved 2019-06-19.
- Hopkins, Anna (2019-06-18). "Orlando Sentinel issues scathing op-ed announcing it won't endorse Donald Trump in 2020 election". Fox News. Retrieved 2019-06-19.
- "Loeb Award winners 1958–1996". Society for Advancing Business Editing and Writing. Retrieved February 6, 2019.
- "Historical Winners List". UCLA Anderson School of Management. Retrieved January 31, 2019.
- Tribune Biography: Mike Bianchi
- Official website (Mobile)
- Today's Orlando Sentinel front page at the Newseum website
- Historical archives of The Orlando Sentinel and The Morning Sentinel freely and openly available as full searchable text and zoomable page images in the Florida Digital Newspaper Library