Etymology

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.^[14]
Although there are at least three major stories as to how Orlando got its name (see below), it is known for certain that the city of Jernigan was renamed 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 [Jernigan's militia] are more dreadful than the Indians."^[15] At a meeting in 1857, debate had grown concerning the name of the town. Pioneer William B. Hull recalled how James Speer (a local resident, and prominent figure in one of the stories behind the naming of Orlando) 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 seat be Orlando."^[15]
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). However, others claim Speer simply used the Orlando Reeves legend to help push his plan for naming the settlement after the Shakespearean character (see below).

Orlando Reeves

The most common story (and the one purported by city officials) is that 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).^[16]
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.^[16] A memorial beside Lake Eola – originally placed by students of Orlando's Cherokee Junior School in 1939^[16] – designates the spot where the city's supposed namesake fell.
There are conflicting legends, however, as an in-depth review of military records in the 1970s and 1980s turned up no record of Orlando Reeves ever existing.^[16] 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; however, not much is known about Acosta or if he even existed.

Orlando Rees

A second variation places the naming around the time of the Second Seminole War. This name is taken from a South Carolinian cattle rancher named Orlando Savage Rees.^[15] 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.^[15] Unlike Orlando Reeves who cannot be traced to any historical record, there is considerable record that Orlando Rees 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.^[15]
In 1837, Rees also attempted to stop a peace treaty with the Seminoles because it did not reimburse him for the loss of slaves and crops; Rees' sugar farms in the area were burned out in the Seminole attacks in 1835 (the year Orlando Reeves supposedly died). Subsequently, Rees led an expedition to recover stolen slaves and cattle. It is believed Rees could have left a pine-bough marker with his name next to the trail; later residents misread "Rees" as "Reeves" and also mistook it as a grave maker.^[15]
In subsequent years this story has merged with the Orlando Reeves story.