Thursday, May 16, 2019

ORLANDO Founding Families: The SPEER Maternal family

Part 7: The SPEER family of ORLANDO, Maternal side

Solving Orlando’s mysterious origin first requires accepting the fact Orlando REEVES is a work of total fiction. He never existed! Now, with that in mind, consider these two important yet little-known clues to solving the mystery: (1) Widower James G. SPEER decided to return to Orange County from Dunedin, Florida after the end of the Civil War; and (2) Thomas H. HARRIS chose to remain there on the Gulf Coast!

Isaphoenia C. (Ellington) Speer, courtesy Winter Garden Heritage Foundation

The story of how Orlando came to be was complicated by a husband and father not wanting to hurt the feelings of those he loved. But the result of James being nice meant Isaphoenia needed to be forgotten! It’s not like he had planned it that way, more like history taking a strange turn!

It was 1868 when Judge Speer (Part 6), after burying Isaphoenia at Dunedin, returned to Orange County to learn James & Sansparillo Jackson had both died. The Jackson’s had purchased the 660 acre Speer estate on Lake Apopka prior to the Speer’s moving to Dunedin. A Jackson daughter, Mary Elizabeth, was living on the property when Judge Speer returned from the Gulf Coast. On February 7, 1869, Mary E. Jackson became James G. Speer’s second wife.

Judge Speer & Mary (Jackson) settled on land each spouse was familiar with, 660 acres that in 1858 had been purchased by the first Mrs. Speer. The second Mrs. Speer had inherited the land from her parents. So, with exception of a brief sojourn during the War, James had lived on the Lake Apopka property with Mrs. Speer for a decade. The only difference was the identity of Mrs. Speer!

Fast forward to 1887 and we find Judge James G. Speer recording a plat for Town of Oakland, a new town on the same 660 acres Mrs. Speer acquired in 1858. Children of the first wife of James G. Speer had married and were raising their own children in the Oakland area by 1887. And so too were children from Judge Speer’s second marriage.

Folks in 1887 were also becoming curious about their county’s history, and who better to ask than Judge James G. Speer. But what was he to say, that it all started because of his first wife?


As Confederates began firing upon Charleston’s Fort Sumter in 1861, Lady Isaphoenia Speer of Orange County had already accumulated 1,700 acres – land deeded in her name and her name alone (see also Part 6). The bulk of Lady Isaphoenia’s 1860 owned land is today the towns of Oakland and Winter Garden, but she owned three strategic parcels along the original Fort Mellon to Fort Gatlin Road too: 40 acres at Fort Reid; 160 acres at Lakes Highland & Ivanhoe; and 160 acres at Lake Pineloch. By War’s end, Lady Isaphoenia had liquidated nearly all of her Orange County property and relocated with Judge Speer to Florida’s Gulf Coast.

Lady Isaphoenia (Ellington) Speer, a native of Abbeville, South Carolina, 7th of 13 children born to John & Obedience H. Ellington, married James G. Speer in 1840. Obedience (Bedy) married John Ellington at Abbeville, SC in 1805, but by 1828, she had become a widow. Three of her 13 children at the time were under the age of 10.

In 1831, Widow Obedience H. Ellington married Widower William Harris Caldwell. Both were getting up there in age, but did have one child together, Benjamin F. Caldwell, born 1834 at Abbeville, prior to the Caldwell’s relocating to Talladega, AL.

William H. Caldwell became legal guardian in 1838 of Isaphoenia C; Parthenia A; and Justivia C Ellington, three girls ages 11, 12 and 14, each a daughter of deceased John Ellington.

At age 16, Isaphoenia C. Ellington married James G. Speer in 1840. Their first child, Catherine, was born the following year in South Carolina. And by 1854, the mother of four moved with her husband James to central Florida. Lady Isaphoenia, on March 27, 1858, made her first of many Orange County land acquisitions. 


1854: James & Isaphoenia Speer arrived in central Florida, but as stated last week in Part Six, their reason for moving to Florida is uncertain. Most new arrivals of that time applied for a free homestead – James Speer did not. Most new arrivals of the time left a legacy in the form of land ownership – James Speer did not. Some believe the Speer’s lived at Fort Gatlin, others say Lake Ivanhoe – but no actual land record exists prior to 1858 substantiating their residence location.

1855: Bedy H. & William H. Caldwell of Talladega, AL recorded a deed at Orange County on June 13th, naming their daughter, Isaphoenia C. Speer; William Harris Caldwell, stepfather of Isaphoenia C. (Ellington) Speer, died October 29th at Talladega. Benjamin F. Caldwell, age 21, was living at Talladega with his wife, Louisa B. Morris. Ben & Louisa had married November 10, 1853 at Talladega. Benjamin became administrator of his father’s estate in October, 1855.

1856: James Speer enlisted with Aaron Jernigan’s Orange County, FL Militia, but so too did a Thomas H. Harris, age 46, and son John Moffett Harris, age 18. The father and son were both named on the March 10, 1856 muster roll. Benjamin F. Caldwell was not listed, but five (5) days later, on March 15, 1856, Benjamin F. Caldwell of Talladega, AL purchased 119 acres of Orange County land that is now downtown Orlando. Meanwhile, back at Talladega, William, the first child of Benjamin & Louisa Caldwell, was born in November of 1856.


1857: John R. Worthington became first Postmaster of Orlando Post Office, opened September 19th, Thomas H. Harris was Orange County’s Justice of the Peace. James G. Speer signed a deed for Benjamin F. Caldwell of Talladega, AL, donating four acres to Orange County for the site of a courthouse; At Talladega, AL on October 31, 1857, Benjamin F. Caldwell signed a power of attorney giving James G. Speer the authority to “take possession of all Caldwell real estate in Orange County and sell, grant or convey” all 119 acres acquired by Benjamin F. Caldwell a year earlier, in 1856.

Village of Orlando had become a reality by September 1857, but who was its founder and why? Speer and Caldwell are understandably the names most associated with the town’s founding, but one important surname, “ELLINGTON,” is missing. Neither Caldwell nor Speer displayed any real interest as developers, so why then did they go through the motions? Was the founding a town of Orlando on their honey-do list?

Fact is, of all central Florida pioneers mentioned thus far, only ONE is of a bloodline leading to ancestors (plural) named ORLANDO. A family connection is not found through Ben Caldwell. Nor is a connection found in the bloodline of James G. Speer. The lineal descendant of the name Orlando is John ELLINGTON (1778-1828), father of Lady ISAPHOENA.

John Ellington was born at Amelia County, VA. His Paternal great-grandmother was Martha EPPES (related to Francis Eppes of Orlando’s Lake Pineloch – and by amazing coincidence, the very same Lake Pineloch Eppes parcel was first owned by Lady Isaphoenia.) John’s Maternal line is where we find the Orlando’s. He was the nephew of Frances Orlando Jones of Virginia, and also a great-grandson of the Honorable ORLANDO Jones (1861-1719) of Williamsburg, VA. (Martha Washington, wife of President George Washington, was also a great granddaughter of Orlando Jones of Williamsburg.

William H. Caldwell, it appears, was in the process of memorializing noble ancestors for his stepchildren, doing so by arranging Orlando as the Orange County’ seat of government. He died before his work was finished, so his young son begrudgingly carried on after his father’s death. William Harris Caldwell didn’t come to the wilderness of Florida to establish a city though, he instead sent a trusted emissary. Families of the Village continues next week with the HARRIS family of Orlando.

Next Friday, May 24, 2019: Thomas H. HARRIS

“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.

Central Florida History by Richard Lee Cronin


CitrusLAND: Curse of Florida’s Paradise, and

First Road to Orlando and Beyond Gatlin: A History of South Orange County

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