1876 — First edition of Orange County Reporter printed.
1903 — Orlando Evening Star becomes a daily newspaper.
1905 — Orange County Reporter becomes a daily newspaper.
1913 — Orlando’s South Florida Sentinel becomes a morning daily newspaper.
1916 — Reporter and Star are combined under one owner.
1931 — South Florida Sentinel, known as the Orlando Morning Sentinel acquires Reporter Star. Martin Andersen comes to Orlando to manage both papers.
1945 — Andersen purchases the Morning Sentinel and Reporter Star.
1965 — Andersen sells his newspapers to Tribune Company of Chicago.
1973 — Morning Sentinel and Reporter Star merge to become a single daily newspaper: Sentinel Star.
1981 — A $28 million production center is added to the original building.
1982 — Paper named The Orlando Sentinel. The parent company is renamed Sentinel Communications Co.
1988 — The Orlando Sentinel wins its first Pulitzer Prize for Jane Healy’s “Florida’s Shame”, an editorial series on mismanaged growth in Central Florida.
1990 — Sentinel Direct is created to serve advertisers’ direct mail needs. The Family Fund is created to give back to the community.
1993 — Sentinel wins 2nd Pulitzer Prize for Jeff Brazil and Steve Berry’s series on Volusia County sheriff’s drug squad and unjust cash seizures. Inaugural Top 100 Companies for Working Families event is held.
1995 — The Orlando Sentinel publishes Orlando Sentinel Online digitally through America Online.
1996 — Orlando Sentinel Online is introduced on the Web.
1997 — Sentinel Communications Co. changes its name to Orlando Sentinel Communications.
1998 — Calendar, Orlando Sentinel’s premier source of entertainment information goes online.
2000 — The Orlando Sentinel wins its 3rd Pulitzer Prize for John Bersia’s “Fleeced in Florida” looking at cash-advance businesses that prey on people. Kathleen M. Waltz is named first female president and publisher of The Orlando Sentinel. The Orlando Sentinel launches its first cover-to-cover redesign since 1982 and drops the “The” to become Orlando Sentinel.
2001 — The weekly, El Sentinel, and its companion website ElSentinel.com are launched. Reading by Nine, today known as One Book One Community, began sharing the importance of youth literacy with our communities.
2003 — The Sentinel expands into Four Corners – where Lake, Orange, Osceola and Polk counties meet.
2004 — A $13 million packaging expansion project is completed.
2007 — Orlando Sentinel, under Tribune Company, becomes a private company.
2008 — New publisher is named; Howard Greenberg, Sun Sentinel’s Publisher, now oversees both media groups. Orlando Sentinel newspaper is redesigned.
2009 — Pink Bash’s inaugural year celebrates the victories over breast cancer while bringing awareness to the cause.
2011 — The business name is changed from Orlando Sentinel Communications to Orlando Sentinel Media Group. Orlando Sentinel Events department is formed bringing marketing to life.
2012 — The Florida Forward series begins bringing current events to the community through panel discussions.
2013 — A Better You is created as a monthly healthy and holistic living publication. TribX is developed bringing digital networks to our clients to extend their reach.
2014 — HypeOrlando is formed and connects local bloggers with the local community. Home Improvement Guide begins, bringing home dwellers solutions to revamp and reimagine. OrlandoSentinel.com along with its family of websites enters the next generation with a state-of-the-art redesign.
2015 — GrowthSpotter comes alive bringing industry news to business leaders. Orlando Signature magazine debuts reaching affluent local readers. Orlando Sentinel is redesigned in direct response to feedback from our readers and the community. Nancy Meyer, publisher of the Hartford Courant Media Group, comes to Central Florida, becoming the second female publisher and CEO.
2018 — The Orlando Sentinel announced the launch of ProSoccerUSA.com, a new national website devoted to Major League Soccer news, analysis and commentary.
2021 — Orlando Sentinel is acquired by MediaNews Group, one of the largest digital and traditional media organizations in the country. Our digital strength grows as we partner with Adtaxi, a leader in digital marketing.
2023 — As consumers’ media habits change, Orlando Sentinel surpasses 67,000 digital subscribers. Digital subscribers get unlimited access to OrlandoSentinel.com and Orlando Sentinel E-Edition — a digital replica of the daily newspaper.