5 Theories Of How Orlando Got Its Name

Originally, Orlando was called Jernigan. It was named after a prosperous cattleman and planter who moved into the area from Georgia, and who later fell out of grace. So, the handful of citizens in town wanted a new name…and that’s where the mystery begins.

It’s theorized that Aaron Jernigan, the aforementioned cattleman, was dismissed as the town’s namesake because of his shoddy command of the local militia. Secretary of War, Jefferson Davis, wrote, concerning Jernigan’s militia, “It is said they are more dreadful than the Indians.” Jernigan was relieved of command in 1856.

So, in 1857, the town name was changed to “Orlando” to honor…ummm…somebody? Let’s take a look at the theories.

Theory #1 – The Brave Soldier

In 1835, soldier Orlando Reeves was on sentry duty at night outside of Fort Gatlin, located near modern day Orlando. Orlando Reeves spotted a Seminole Indian wading through the water in a sneak attack. He fired a shot to alert his comrades who were camping outside the fort’s walls. Orlando Reeves lost his life, but, due to his bravery, his comrades were able to rally and fight off the attack.

Orlando Reeves was buried there, and later, when people passed through they would say, “There lies Orlando.” and the the name stuck. Or that’s how the story goes…

That story was accepted for some time until a newspaper story from 1884 came to light and complicated things. In it, the brave soldier is identified as Orlando Jennings, not Orlando Reeves.

Researches set out to settle the dispute. They consulted War Department records that listed all 1,466 soldiers killed in the Seminole Wars. To their surprise, they found neither Orlando Reeves nor Orlando Jennings.

Further research confused things more. Instead, they found a wealthy plantation owner named Orlando J. Rees.

Theory #2 – The Wealthy Plantation Owner

Theory number two raises more questions than answers, but here’s what we know: Orlando J. Rees lived near Fort Gatlin in the 1830’s and was nicknamed “Colonel,” despite the fact that he never served in the military. In 1837, Rees wrote a letter to the U.S. government complaining that he had trouble with the Seminole Indians. They kept stealing his slaves (those jerks!).

Here’s where the mystery starts. The 1840 census indicated he wasn’t in Central Florida anymore. Where did he go? Did he pack up and leave? Was he killed by the Seminoles? And if he was killed, did his story give birth to the story of the soldier? Orlando J. Rees’ name is very similar to the soldier’s name, Orlando Reeves. Hmmm…

Theory #3 – Mr. Orlando

A long standing legend has a “Mr. Orlando” transferring ox to Tampa. He never made it there; instead he died and was buried near Fort Gatlin. Later, people passing through said, “There lies Orlando.” That’s the whole story.

Theory #4 – Shakespeare

One of the early and influential men in the area was a South Carolina judge by the name of James Speer. He moved to Florida in 1854 and was instrumental in organizing Orange County and moving the county seat from Enterprise to Orlando. It’s also said he was a big fan of Shakespeare.

So the legend goes that Speer pushed for the town to have the Shakespearian name Orlando; which is a character in Shakespeare’s comedy As You Like It.

The theory gains a little more steam when one considers that one of Orlando’s major downtown streets is named Rosalind, which is the heroine from the same play. According to the pioneer, William B. Hull, Speer rose in the town meeting 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.”

If the story is true, it seems there may have been a grave, supporting the earlier theories, but then again James Speer was clever and may have simply been pulling on local folklore to push for the Shakespearian name.

But, maybe there wasn’t ever a grave…

Theory #5 – A Plantation Owner Carved His Name On A Tree

In this story, a man named Orlando Reeves (yup, same name from theory #1) owned a sugar mill and plantation north of Orlando. He carved his name in a tree near present day Lake Eola. Later, people thought it was a grave marker so they called the place “Orlando’s Grave.”

In Conclusion…

All of the tales contain references to “Orlando’s Grave” so that has to count for something, but it sounds like it is debatable if there was a real grave or just a story of a grave.

I think that Theory #4, about Shakespeare and the judge, is the most probable as to Orlando officially being recognized as Orlando, however, it still does not answer the question about the origins of where the name “Orlando” came from. This one is a real head-scratcher.

What do you think?

(Updated 09/18/2019)