CENTRAL FLORIDA'S FASCINATING HISTORY: ORLANDO Founding Families: The CALDWELL Family

The CALDWELL family of Talladega, Alabama

Historians, when talking origins of Orlando, typically call out the name Caldwell among the town’s possible founders, but usually name the wrong Caldwell! But the mistaken Caldwell identity is understandable in light of all we now know.

Orlando circa 1880s, 24 years after its founding

Rollins College President and historian William F. Blackman, in 1927, introduced “Benjamin F. Caldwell of Talladega, Alabama.” As founder evidence goes, Blackman’s research had indeed been convincing. Referencing an Orange County deed, Benjamin F. Caldwell of Caldwell gave four acres of land for a courthouse. The deed also identified the land around the courthouse site as “Town of Orlando.” Case closed! But was the town’s founding that cut and dry?

Recorded October 5, 1857, the deed described Town of Orlando as 417’ x 417’ square – or four acres. The village included twelve (12) town lots, eleven of which were gifted to Orange County as well. A 100’ x 100’ square Lot 10 was excluded from the land given to the county. Oddly, Orlando wasn’t located alongside a lake, so in the 1870s a well – shown above out from of the courthouse - became the town’s source for drinking water.

When looking over Caldwell’s deed two questions immediately came to mind. Who was this guy Caldwell, and why did he include the eleven town lots with his gift of land? If Benjamin was a developer, it’s easy to understand why he wanted the courthouse at center of his property. But why give away his land around the courthouse?

The only way for me to answer these questions was to learn more about this person Benjamin Franklin Caldwell. And so, I did! I found he was 16 years old in 1850 and living at Talladega with his parents, William H. & Obedience H. Caldwell. I was then surprised to find Benjamin’s parents in pre-1857 Orange County deeds. One such deed, signed in 1855 by William H. & Obedience H. Caldwell of Talladega, identified their child who at the time was an Orange County resident – and that child was not Benjamin!

William H. Caldwell died in 1855. Benjamin, at that time age 21, became administrator of his father’s estate. So, learning this information, a second look at Benjamin’s 1857 deed found it had also been signed off by a probate judge. Benjamin F. Caldwell was serving as administrator of his father’s estate when he donated Orange County’s courthouse land.

Caldwell family in 1850 Talladega, Alabama census

At the time of his death William H. Caldwell of Talladega was land rich. He had accumulated thousands of Alabama acres, plus some land in Florida. Ben had his hands full in resolving his father’s Alabama estate, and so he turned to his brother in law in Florida to assist in resolving the Orange County matter, a “matter” begun by his father for the benefit of Benjamin’s sister. (An older half-sister to be exact!)

The Florida matter had begun around 1854, while the father was still very much alive. It was at that time that Benjamin’s half-sister moved to Orange County, Florida. UCF Professor Paul W. Wehr, author of ‘From Mosquito to Orange County,’ published by the Pine Castle Historical Society, unearthed an interesting fact about Ben Caldwell.

Professor Wehr located a land office record showing Benjamin F. Caldwell purchased 119.95 acres of Orange County land March 15, 1856, paying $1.25 per acre. The importance of this document is its date, for it precedes recorded land deeds of 1857 and 1858 mentioned earlier in this Families of the Village series.

Caldwell and Patrick families both believed they owned the same parcel at the same time!

Although the Caldwell’s lived at Talladega, Benjamin was a native of Abbeville, SC. So too was his half-sister, but she was living in Orange County as of 1854. Benjamin F. Caldwell NEVER lived in the Village of Orlando, and only lived in Orange County for less than a year. (Benjamin arrived at Lake Apopka circa Christmas 1857 and departed circa Christmas 1858.

Benjamin Caldwell’s half-sister meanwhile had accumulated 1,700 acres throughout Orange County – all land deeded in her name alone. Like her step-father, Benjamin’s half-sister was also land rich!

Benjamin’s half-sister was the first wife of James G. Speer. And the Caldwell deed giving four acres to Orange County was signed by James G. Speer, but his signature was backed up by a power of attorney - signed by Benjamin F. Caldwell of Talladega. In other words, Benjamin had given Speer full authority to get rid of all of Caldwell’s Orange County land.

What then does all this mean? William Harris Caldwell, it appears, set out to establish a Florida town named for ancestors of his wife’s daughter, Benjamin’s half-sister, the first wife of James G. Speer. The ancestor was on the deceased husband's side of Benjamin's mother. In the process, William died, and so his son, not interested in being involved with this family matter, gave the Speer’s authority to complete the town building process if they so desired.

After finally closing out his father’s Talladega estate, Benjamin tried living near his half-sister in West Orange County, but that experiment lasted only a year. By Christmas 1858, the Caldwell’s were heading west to Cass County, Texas. Then came the Civil War, and Ben enlisted with the Texas Calvary. Benjamin F. Caldwell, in 1864, died as a result of friendly fire. Following his 1864 death in Texas, and except for a deed mentioning his name, Orlando lost all knowledge of a founder named Benjamin F. Caldwell of Talladega, Alabama.

Caldwell family in Cass County, Texas 1860 Census including Ben's mother "Bedy H"

To a certain extent, Orange County history also forgot about Ben’s half-sister, Isaphoenia C. (Ellington) Speer. But we did not forget, and her story comes next, when Families of the Village continues next Friday, May 10, 2019.

Friday, May 10, 2019: Isaphoenia C. (Ellington) SPEER

“First Road to Orlando” is a history of the old Fort Mellon to Fort Gatlin Road and of how a tiny village in the middle of a remote wilderness became the Orange County seat of government.

Orlando Founding Families Series delves deeper into the courageous pioneers who found their way along a lonely dusty forts trail – to become the first families to settle at Orlando.

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