Prior to being known by its current name, Orlando was known as Jernigan. This originates from the first permanent settler, Aaron Jernigan, a cattleman who acquired land along Lake Holden by the terms of the Armed Occupation Act of 1842.
City officials and local legend say the name Orlando originated from a soldier named Orlando Reeves who died in 1835 during a supposed attack by Native Americans in the area during the Second Seminole War. Reeves was acting as a sentinel for a company of soldiers that had set up camp for the night on the banks of Sandy Beach Lake (now Lake Eola). There are conflicting legends, however, as an in-depth reviews of military records in the 1970s and 1980s turned up no record of Orlando Reeves ever existing. The legend grew throughout the early 1900s, particularly with local historian Kena Fries' retelling in various writings and on local radio station WDBO in 1929. A memorial beside Lake Eola – originally placed by students of Orlando's Cherokee Junior School in 1939 – designates the spot where the city's supposed namesake fell.
Local historians have come up with a more credible version of the "Reeves" story. During the Second Seminole War, the U.S. Army established an outpost at Fort Gatlin, a few miles south of the modern downtown, in 1838, but it was quickly abandoned when the war came to an end. Most pioneers did not arrive until after the Third Seminole War in the 1850s. Many early residents made their living by cattle ranching. One such resident was a South Carolinian Orlando Savage Rees. Rees owned several large estates in Florida and Mississippi. On two separate occasions, relatives of Rees claimed their ancestor was the namesake of the city. F.K. Bull of South Carolina (Rees' great-grandson) told an Orlando reporter of a story in 1955; years later, Charles M. Bull Jr. of Orlando (Rees' great-great-grandson) offered local historians similar information.[9] Rees most certainly did exist and was in Florida during that time period: in 1832 John James Audubon met with Rees in his large estate at Spring Garden, about 45 minutes away from Orlando. In 1837, Rees also attempted to stop a peace Treaty with the Indians because it did not reimburse him for the loss of slaves and crops. The story goes Rees' sugar farms in the area were burned out in the Seminole attacks in 1835 (the year Orlando Reeves supposedly died). Subsequently, he led an expedition to recover stolen slaves and cattle. It is believed he could have left a pine-bough marker with his name next to the trail, and later residents misread the sign as "Reeves" and thought it was grave. In the years since the telling of this story, it has merged with the Orlando Reeves story. Some variants attempt to account for Reeves having no military records by using the name of another 'Orlando' that exists in some written records – Orlando Acosta. Not much is known about Acosta and if he even existed.
In 1975, local historian, and then chairman of the county historical commission, Judge Donald A. Cheney put forth a new version of the story in an Orlando Sentinel article. Cheney is the son of Judge John Moses Cheney, a major figure in Orlando's history who arrived in Orlando in 1885. John Cheney knew James Speer – another major figure who proposed the name of Orlando. Cheney's retelling relates how Speer proposed the name Orlando after one of the main characters in the Shakespeare play As You Like It. Speer, "was a gentleman of culture and an admirer of William Shakespeare...According to him, was a veritable Forest of Arden, the locale of As You Like It." One of the main streets in downtown Orlando is named Rosalind Avenue, after Rosalind, the heroine of the play. Speer's descendants have also confirmed this version of the naming and the legend has continued to grow.
What is known for certain is Jernigan became Orlando in 1857. The move is believed to be sparked, in part, by Aaron Jernigan's fall from grace after he was relieved of his military command by military officials in 1856. His behavior was so notorious that Secretary of War Jefferson Davis wrote, "It is said they are more dreadful than the Indians." At a meeting in 1857, debate had grown concerning the name of the town. Pioneer William B. Hull recalled how Speer rose in the heat of the argument and said, "This place is often spoken of as 'Orlando's Grave.' Let's drop the word 'grave' and let the county set be Orlando." Through this retelling of history, it is believed that a marker of some sort was indeed found by Jernigan (or one of the other original pioneers); but, others claim Speer simply used the folk legend to help push for the Shakespearian name.