Dr⁠i⁠pp⁠i⁠ng H⁠i⁠s⁠t⁠ory: Book Explores Los⁠t⁠ Legacy of Cha⁠i⁠res, Verdura

By: The James Madison Institute / 2016



If you were born and raised in Tallahassee, and have a sense of history, you may very well have heard of the Chaires family, and the name “Verdura,” by many accounts, the grandest plantation in Middle Florida — the area between the Suwanee and Apalachicola rivers.

Benjamin Chaires and “Verdura” epitomize the grandeur of the Old South, the horror of slavery that accompanied it, and the ultimate tragedy of hubris that befell it. Now, in Sharyn Heiland Shields’ “Whispers From Verdura: The Lost Legacy of Benjamin Chaires,” published by Tallahassee’s Sentry Press, is available directly from the author beginning this week, you can read about this Faulknerian man and the fate of his family and himself.

Shields, formerly with the Division of Historical Resources, Department of State, has spent nearly 20 years researching and studying Benjamin Chaires, his family and his plantation, “Verdura.” What she discovered was, encapsulated in one family, the story of the Cotton South before and after what many Southerners used to call the “Late Unpleasantness,” including the various misjudgments and tragedies that befell the family.

“Ben Chaires absolutely epitomizes that class of young, go-getting, get-rich quick planters who migrated to Middle Florida after 1821 and made it part of The Cotton Kingdom,” said Dr. William Warren Rogers. “There are many historians who consider him the first true millionaire in Florida, and I would say that is not far wrong.”

FSU history professor Katherine Mooney said it is very difficult to overestimate the economic fervor that drew people to Florida and what was then called the Southwest territories of Alabama and Mississippi in the first few decades of the 19th century.

“You never saw people get so rich so fast in this country until the advent of Silicon Valley, of which this reminds me. Get some land, get a few slaves, grow some cotton and you’re on your way,” Mooney said. “It was the dot-com revolution of its day.”

45,000 acres, 300 slaves

Benjamin Chaires, born in North Carolina in 1786, realized early that his future lay in land and slaves. He accumulated hundreds of acres in Georgia before migrating to the Georgia coast and East Florida just before the United States acquired Florida from Spain in 1821. He accumulated land near Jacksonville and St. Augustine prior to moving to Leon County after Tallahassee became the territorial capital.

“I estimate that he owned as much as 45,000 acres in Florida,” Shields said. “He owned, at various times, between 100 and 300 slaves at Verdura, and there is really no telling how many at all of his plantations, whether he moved them around, bought and sold new ones, or just how he distributed his labor force.”

Chaires was not always, according to Shields, the prescient civic leader and capable business man one would expect from the myths surrounding his life.

“He had some interactions with Zepheniah Kingsley over near Jacksonville,” Shields said. “The two were involved in a lawsuit over Chaires cutting timber on a plantation Kingsley managed. Kingsley, you know, did really have revolutionary — and to most of the other planters in Florida — threatening views about slavery. But, there is no evidence that Chaires shared them.”

Tracing the documents

In fact, Shields said that one of the most disturbing documents she found in her research was written by a northern college student named Amos Dresser. The year 1835 was a key one in the rise of the anti-slavery movement in the U.S. Following the Nat Turner revolt in 1831 and the beginning of publications like The Liberator, edited by William Lloyd Garrison in Boston, it did not take much to alarm Southern slave owners.

There were rumors in 1835 of a massive slave revolt set for Christmas in New Orleans, supposedly instigated by something called the Mystic Clan and associated with John Murrell, a notorious horse thief and criminal; the Tappan Brothers of New York (very wealthy abolitionists) flooded the Southern mails with anti-slavery literature (which led to the public burning of mail in Charleston with the permission of the Jackson Administration), and then there was Dresser.

“He was an Oberlin student, which was a center of abolitionist sentiment,” Shields said, “who decided to travel through the South and observe slavery and slave owners. He did not particularly hide his mission, and he was not well-received. In Nashville, for example, he was flogged and ordered to leave town.”

Dresser eventually made his way to Tallahassee where his memoirs mention an interview with “Col. W,” possibly George T. Ward, Benjamin Chaires’ son-in-law and the owner of nearby Southwood Plantation, who told him that, yes, slavery was a brutal institution, but that it was justified because of the value of the product: cotton.

“That story does reinforce how horrible slavery was,” Shields said, “but how off-handed and matter-of-fact it was, too. In the decades leading up to the Civil War, the entire U.S. economy was dependent on Southern agriculture and slavery. Cotton was 60 percent of all U.S. exports in 1860. So, whether or not it was pure capitalism, slavery was certainly a part of a world-wide market economy.”

Little time to live in Verdura

Once Benjamin Chaires settled in Middle Florida, he quickly became part of a political organization called “The Nucleus” centered around friends and supporters of Andrew Jackson, who was elected president in 1828. Chaires’ interactions with figures such as William P. DuVal (who contracted with Chaires to provide rations for the Seminoles whom the Jackson Administration was trying to force out of the territory), Richard Keith Call, and others, made him a very prominent figure.

Chaires was one of the founders of the Magnolia and Central Banks, invested in railroads, and may have provided bricks for the construction of The Columns (present home of the James Madison Institute) where he lived temporarily while Verdura was being built. He was scheduled to be a delegate to Florida’s first constitutional convention in the coastal town of St. Joseph, but took ill and died, almost certainly of yellow fever. He barely had time to live in Verdura. Chaires died in 1838 at age 52.

For someone as prominent as Chaires was at the time, it is surprising that there are no confirmed portraits of him. Shields has one that may be him, sent by a family descendent, but authenticating it has been impossible. For years, a portrait of his wife hung over one of the mantles in The Columns, but it seems to have disappeared and Shields says, “Finding it is on my to-do list.”

As for “Verdura” itself, there is only one known image of the mansion before it burned in the 1880s, a pencil drawing that shows a three story dwelling with five columns on each side. It was indeed a very impressive structure, and certainly epitomized the grandeur of a wealthy plantation owner’s home.

In some ways, of course, what happened to Verdura and the Chaires family was typical of what happened after the death of a patriarch like Benjamin Chaires: squabbles over land, taxes, decreasing crop yields, and finally, of course, the Civil War, and the loss of a labor force that underpinned the whole culture. Throw in a family sex scandal that ultimately resulted in the mysterious death of Benjamin Chaires’ youngest son, and you have the stuff of Southern Gothic fiction at its finest.

Shields will be signing books on Sunday, July 17 from 2-5 p.m. in the Jubilee Cottage at Goodwood Plantation.

Bob Holladay teaches in the History Department of Tallahassee Community College. He in the managing editor of Sentry Press. Email him at

About the book

“Whispers from Verdura: The Lost Legacy of Benjamin Chaires,” by Sharyn Heiland Shields has been published in a limited edition of 400 copies, 100 hardback and 300 paperback by Sentry Press if Tallahassee. The hardbacks will retail for $30, the paperbacks for $15. The book will ultimately be distributed to appropriate historical sites with gift shops, with one hundred percent of sales going to the sites’ related support groups. The book will also be donated to libraries and archives.

Book signing

Shields will be signing books on Sunday, July 17, from 2-5 p.m. in the Jubilee Cottage at Goodwood Plantation. To order copies of the book, contact her at Payment must be by cash, check or money order.