In Search of Citrusland, Part 2

Moses Lyman (Left); Benjamin F. Whitner II (right)

In Search of Florida’s Historic Citrusland

Part 2: Florida’s Sweet Orange Peace Pact

“In 1869, when your correspondent arrived in Orange County, the orange crop was estimated at 60,000. I see by the figures of the Florida Journal that the shipments of the present year (1877) at Mellonville, Sanford, and Lake Jesup, are put down (estimated) at 2,000,000.”

Will Wallace Harney, Cincinnati Commercial Newspaper

April 15, 1877

A Historic Flash Back!

Benjamin Franklin Whitner II, “Junior” as he proudly wanted to be known when signing surveys in 1843, was born in 1819 in Cambridge, South Carolina, an Abbeville County town very much in decline at the time of his birth. Five years later, in 1824, Isaphoenia Cleopatra Ellington was born in Abbeville, South Carolina. Ten years after her birth, Benjamin Franklin Caldwell, in 1834, was also born in Abbeville, South Carolina.

Part One of In Search of Florida’s Historic Citrusland introduced Surveyor Benjamin F. Whitner II as being the first known non-military White person to step foot on soil south of Lake Monroe in the aftermath of the Second Seminole Indian War. Whitner was also the first of a half-dozen or so surveyors assigned the task of mapping that which is today Orange, Osceola, Seminole and Lake Counties.

Despite being the first surveyor to arrive for the task at hand, however, Whitner traversed deep into the wilderness, 23 miles to be exact, following the sand-rutted military trail south, prior to setting up his instruments and beginning his surveying and mapping of the territory. The first land Whitner surveyed was a 36 square-mile area that included Fort Gatlin and the nearby land that was to become the residence, in 1871, of the grandson of President Thomas Jefferson.

Also introduced in Part One of this Blog was Isaphoenia Cleopatra (Ellington) Speer, the first wife of James G. Speer. James and Isaphoenia arrived in Orange County in 1854, nearly two years before the town of Orlando was established. The Speer’s lived first on the east shore of Lake Ivanhoe, a mile north of the future town of Orlando, the 1856-57 village which James G. Speer is most often credited with having founded. The Lake Ivanhoe land upon which the Speer’s resided was deeded in her name only, as was another 160-acre parcel further south, deeded to Isaphoenia C. Speer in 1860. Fronting on Lake Pineloch, this latter parcel became the exact parcel upon which President Thomas Jefferson’s grandson, Francis Wayles Eppes, built his residence in 1871.

A name not mentioned in Part One of this Blog was Benjamin Franklin Caldwell, a half-brother of Lady Isaphoenia (Ellington) Speer. Benjamin and Isaphoenia shared the same mother, who had remarried after the death of Isaphoenia’s father, John Ellington (1778-1828).

Benjamin F. Caldwell’s parents relocated from Abbeville, South Carolina, where he was born in 1834, to Talladega, Alabama. Benjamin, serving in 1857 as Administrator of his father’s estate, became etched in the baffling story of how Orlando came to be as the mysterious “Benjamin F. Caldwell of Talladega, Alabama,” donor of four acres for an Orange County courthouse. The 1857 deed to the County from Caldwell specifically states a “town Plat of Orlando.” (Dare I put it in print again? Oh, why not! Orlando was first Platted as a town in 1857, not 1875.)

Government surveyors in the 1830 and 40s worked their way south in the Florida Territory from the Georgia line, continuing their way south when, in 1845, Florida became the 27^th State. Most of the Central Florida area was surveyed between 1843 and 1850, after which, most of those who were doing the survey work went west. Not so, however, of Benjamin Franklin Whitner II.

After surveying much of the land south of Orlando, as far south as Lake Tohopekaliga, where the town of Kissimmee was to be established, Benjamin F. Whitner began acquiring Orange County property. In the early 1850s, Whitner II purchased nearly 140 acres adjacent to Fort Gatlin, land he had first surveyed in 1843.

During the year 1860, Whitner acquired an additional 160 acres at Fort Gatlin. Isaphoenia C. Speer, in her name and her name alone, also bought 160 acres north of Fort Gatlin. Located on the east shore of Lake Pineloch, the Fort Mellon to Fort Gatlin Road crossed Isaphoenia’s property on its way toward the entrance to Fort Gatlin.

The very same year Whitner and Isaphoena bought their two 160-acre parcels near Fort Gatlin, Isaphoenia’s half-brother, Benjamin F. Caldwell, was issued a homestead deed for 120 acres, land along the Fort Mellon to Fort Gatlin Road of 1838, land that is today Magnolia Avenue in downtown Orlando, land that included four acres Caldwell had donated to Orange County in 1857 for a courthouse, land that had identified as including “the Town Plat of Orlando”

Town Plat of Orlando, Recorded October 5, 1857

A Curious Cancelled Deed:

Early records of the Orange County Comptroller include an 1868 deed that was cancelled in 1869.  A land sales deed dated December 21, 1868, the seller was identified as “James G. Speer of Hillsborough County.” Speer had sold a parcel of land to William W. Barber described as the “Northwest Quarter of Section Twelve, in Township 23 South, Range 29 East, consisting of 159.57 acres.”

The parcel James Speer sold to Barber is the exact same parcel I refer to as the “Eppes-Trist Homestead,” the acreage upon which Francis Eppes built his home in 1871. The land sales deed of 1868, however, contains a scribbled note stating the deed was “cancelled by consent of both parties on September 18, 1869.”

Credited with founding Orlando in 1856-57, and later credited as the founder of Oakland in West Orange County, why did James G. Speer, in the year 1868, identify himself as a resident of Hillsborough County? Also, why was the 1868 land sale cancelled?

A short answer about why James Speer’s land sale of 1868 was cancelled is this, he didn’t own the property! And Speer signed as a resident of Hillsborough County because that is where he and his family lived in 1868. Where he lived, however, requires further explanation. James and Isaphoenia Speer departed Orange County and settled near present-day Dunedin after the Civil War. Now in Pinellas County, the Dunedin area, in 1868, was still part of Hillsborough County.

Isaphoenia Cleopatra (Ellington) Speer died in 1867 at the age of 43 near where the town of Dunedin, Florida is today. Deceased in 1868 when her husband James G. Speer, a widower, attempted to sell 160 acres that had been deeded in Isaphoenia’s name alone, the 1868 deed was cancelled September 18, 1869, because the sale had not been processed through Probate Court.

The very same 160-acre property that James G. Speer attempted to sell was then conveyed to another owner within months. A New Orleans Attorney, William Mayer Randolph, acquired the 160-acre parcel, but not for himself. Randolph had already purchased acreage about a half mile further south on the Fort Mellon to Fort Gatlin Road. Randolph instead gave half of the former “Isaphoenia Speer” parcel to Francis Wayles Eppes of Tallahassee on the condition that Eppes could reimburse Randolph for the cost of the land when financially capable. The other 80 acres was deeded to Nicholas Philip Trist of Alexandria, Virginia.

Happenstance of Intentional?

Was it merely happenstance that Francis Eppes and Nicholas Trist ended up owning the same 160-acre parcel on the western shore of Lake Pineloch that Isaphoenia Speer owned a decade earlier? You decide!

Isaphoenia Cleopatra (Ellington) Speer was a fascinating Central Florida frontierswoman who totally slipped through the cracks of Florida’s history. By 1860, this lady owned more land in Orange County than any other man or woman. Women were seldom the sole-landowner at that time in our history. Orange County recorded documents show that Isaphoenia owned nearly 1,700 acres as of 1860, and yet no one ever appears to have asked why. No one ever seems to have asked what I believe is the most obvious question, who was Isaphoenia?

So, allow me to answer the question for you:

Isaphoenia Cleopatra (Ellington) Speer was a half-sister of Benjamin Franklin Caldwell (both had the same mother). Benjamin F. Caldwell of Talladega, Alabama, was the known individual who, on October 5, 1857, gave the four-acres to Orange County for a courthouse. The parcel, at the corner of Central Avenue and Magnolia Street, much of which is now Heritage Square, is the entrance to the Orange County History Museum. James G. Speer, Isaphoenia’s husband, merely acted as Benjamin F. Caldwell’s Attorney in the land donation to the county.

Isaphoenia Cleopatra (Ellington) Speer was the Great-Great Granddaughter of Orlando Jones (1681-1719) of Williamsburg, Virginia. First born in the New World, Orlando was the son of Reverend Rowland Jones (1640-1688), a native of England who then became Pastor of Bruton Parish in Williamsburg. (Note: In William Shakespeare’s play, ‘As You Like It,’ the character Orlando, the son of Rowland, flees his homeland to live in the forest of Arden. In the history archives of Orlando, Florida, James G. Speer is recorded as being a fan of Shakespear’s play, “As You Like it.” Was James the play’s fan or was it Isaphoenia Cleopatra (Ellington) Speer?)

Isaphoenia Cleopatra (Ellington) Speer’s Great-Great Grandfather, Orlando Jones, was also the grandfather of Martha (Dandridge) Custis Washington (1731-1802), First Lady of our first President, George Washington (1732-1799).

Isaphoenia Cleopatra (Ellington) Speer was also the Great Granddaughter of Martha (Eppes) Tucker. Martha had been the daughter of Colonel Francis Eppes III, a Patriot of the American Revolution, the ancestor for whom Francis Wayles Eppes had been named. So, was it merely a coincidence that Francis Eppes, grandson of President Thomas Jefferson, chose to build his new Orange County home on land that had previously been owned by a lineal descendant of Colonel Francis Eppes III and a descendant of the grandfather of our Nation’s first, First Lady?

Also, is it reasonable to assume James G. Speer founded Orlando, or merely completed a honey-do project for his first wife, the amazing, Isaphoenia Cleopatra (Ellington) Speer?

Florida’s Sweet Orange Peace Pact 

Benjamin F. Whitner II (left), Onora (aka Onoro), Fort Reid, Florida

“He secured a “Yankee” to furnish capital and he the experience, and to divide equally.”

Plain Talk About Florida, John Angus MacDonald (1883)

Orlando’s founding in 1857, followed in 1860 with land investments along the Fort Mellon to Fort Gatlin Road, appears to have been a prelude to something bigger in the works – likely a railroad - opening-up Orange County’s wilderness to prosperity. But whatever the locals had in mind for 1860, plans soon came to an abrupt halt by the Civil War. After War’s end, with casualties estimated in excess of 600,000 Americans, the future looked bleak for the war-torn South. One-third of Orange County’s young men had died in the War, although in 1867 many a Floridian household was holding out hope that their loved ones might still be on their way home. Benjamin F. Caldwell of Talladega, however, the young man who had established Orlando, was dead. And in 1867, his half-sister, Isaphoenia Cleopatra (Ellington) Speer, died.

“How my hopes were buoyed up, in 1868,” wrote John Angus MacDonald of Orange County in 1882, “when Colonel B. F. Whitner, an old North Florida planter, decided to leave North Florida, where the subtropical fruits could not be grown successfully, and to come to Orange County to plant a large orange grove. He secured a “Yankee” to furnish capital and he the experience, and to divide equally.” He bought the property on which I slept the first night in Orange County (in 1867), at about $650.00 for 110 acres, a beautiful spot, and commenced work. The place is now one of the finest in Florida.” The property acquired was one mile south of Fort Reid, upon which were Lakes Golden, Onora and Silver (see photo above).

The significance of the above paragraph is easily lost today. And the magnitude of MacDonald’s words, written in 1882, words supported in fact by Orange County documents recorded during the 1870s, have long been overlooked by historians throughout the ages. Although the war had ended, the Reconstruction Period had only just begun. Guns had fallen silent only two years prior, and the State of Florida was still under Marshal Law. Union Gunboats patrolled the St. John’s River, stopping often at Mellonville on Lake Monroe – location today of Sanford.

“The change wrought by the war in the circumstances of thousands is great,” wrote one Orange County, Florida resident as reported in the Clark County Democrat of 9 April 1868, “and they have longed for some field in which to start fresh the struggle of life.” Orange County needed a hero more than ever to come forward in 1867, and Orange County was about to get just such a person. Twenty-five years after sketching the location of Fort Gatlin on his survey of Mosquito County, Benjamin Franklin Whitner II was preparing to complete his dream for Orange County that had been interrupted by war. Problem was, he needed assistance. And he needed to make peace if he was to get that assistance he, and his beloved Central Florida, desperately needed.

“Moses Lyman leaves in a few days for New York,” said Connecticut’s Litchfield Journal of 19 December 1867, a story updated on 23 January 1868 with the addition, “Moses Lyman, Esquire, has safely arrived at Madison, Florida.” A successful iron manufacturer in the northeast, Lyman, a Union supporter, traveled into the war-torn South to Madison, the hometown of Benjamin F. Whitner II.

As revealed in Chapter 10 of my book, Orlando: A History of the Phenomenal City, Benjamin F. Whitner II and Moses Lyman came to Orange County and partnered in acquiring “The Mundy Place,” an abandoned homestead located about one mile south of present-day Sanford. Charles Mundy had died during the war, and Whitner traveled to Virginia to strike a deal with his heirs to acquire the land, a transaction he completed in July 1868.

A Yankee and a Southerner, within three short years of the Civil War ending, made peace. More than peace in fact, for Moses Lyman and Benjamin Whitner also laid the foundation – albeit a shaky and unstable one at best – for an industry that was to forever change the future of our State of Florida.

Lyman and Whitner, however, did not invent oranges. What they accomplished altered the fruit’s importance in an otherwise isolated State. Next week, In Search of Citrusland, Part 3, takes a closer look at Florida’s 19^th Century Oranges prior to Citrusland.

Mr. Cronin Goes to Washington, to discuss Mr. Smith coming to Florida!

An In-Person Presentation at Florida House

The One and Only State Embassy in DC

April 28, 2026

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