Nec temere, nec timide

(Neither rashly, nor timidly)

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About the Freeman Family

The Freeman family history is a rich tapestry woven from centuries of migration, hard work, and dedicated service to community and country. Rooted in early American colonial settlements, our story spans from 17th-century English migrants in Virginia to patriots and pioneering farmers in South Carolina and Mississippi, and onward to modern entrepreneurs and philanthropists.

Colonial Origins: From England to Virginia

The Freeman family’s American journey begins with Henry Freeman (c. 1610–c. 1670s), born in England and migrating to Virginia around 1635 with his brother William. As early planters in James City or York County, they established tobacco farms amid the burgeoning colony. Henry’s son, William Freeman (c. 1640s–c. 1710), relocated to Colleton County, South Carolina, around 1711 with his wife Elizabeth, shifting the family southward into rice and indigo cultivation.

Subsequent generations in South Carolina, including John Freeman (born 1734 in Colleton County; died after 1774) and his son Isaac Freeman (born October 24, 1760, in Orangeburg, South Carolina; died c. 1820 in Amite County, Mississippi), navigated the Revolutionary era. Isaac married Catherine Crockett and fathered at least eight children, including John Freeman (1793–1860). Around 1816, Isaac migrated to Mississippi, drawn by land opportunities in the newly formed state.

Settlement in Mississippi: The Frontier Farmers

John Freeman (born May 28, 1793, in South Carolina; died 1860 in Franklin County, Mississippi) married Mary Smith on November 21, 1818, in Amite County. They raised eight children, including John Crockett Freeman (born April 10, 1819; died 1863), while farming across Amite (1820 census), Copiah (1830–1840), and Franklin Counties (1860). John Crockett, married Nancy Whittington (daughter of Revolutionary War veteran Richard Whittington) on April 13, 1844, in Amite County. They had at least eight children, including David Crockett Freeman (born 1849).

David Crockett Freeman, named in homage to distant relative and frontier icon Davy Crockett (an American politician, militia officer and frontiersman. Often referred to in popular culture as the “King of the Wild Frontier”, he represented Tennessee in the United States House of Representatives, fought in the Texas Revolution, and died at the Alamo in 1836. Roy Jr. is 3rd cousins 6 times removed to Davy Crockett), married Ottie Jane Reynolds on December 17, 1885, in Franklin County, fathering sons Jerome (1884–1940) and John Adam Freeman (1887–1940). John Adam, a lifelong Franklin County farmer, married Lonie Tarver (or Lonnie Foster in some records) and had seven children, including Wince “Jim” Freeman (born 1920; died January 4, 2004, Roy Jr.’s “Paw Paw”).

The McKenzie-Lewis Connection: Revolutionary Roots

Through marriage, the Freeman line intertwines with the McKenzie family, descendants of Joseph Benjamin Lewis (born September 30, 1763, in Saluda County, South Carolina; died March 24, 1845, in Copiah County, Mississippi).

Joseph served as a Private in the 3rd South Carolina Regiment under General Francis Marion (“Swamp Fox”) during the Revolutionary War, contributing to guerrilla campaigns. Marion was one of the influences for the main character of Benjamin Martin (Mel Gibson) in the 2000 movie The Patriot.

Recognized in DAR Rolls of Honor, Joseph married Sara Elizabeth MaGee (16 children) and later Tabitha Morris, migrating from South Carolina to Georgia and Mississippi.

Joseph’s daughter Nancy Lewis (c. 1784) married David McKenzie, carrying the line westward. Descendants settled in Marion, Pike, and Franklin Counties, leading to William Ottice McKenzie (1894–1957), father of Elsie Alice McKenzie (1912–1992). Elsie married Wince Freeman, uniting the lines.

20th Century: Wince Freeman and Roy W. Freeman Sr.

Wince “Jim” Freeman (1920–2004), a devoted farmer in Smithdale, Mississippi, married Elsie Alice McKenzie. They raised their family with strong ties to the Temple Hill Church of Christ, instilling values of integrity and community. Wince passed away while his grandson Roy Winston Freeman Jr. was in U.S. Army medic training in 2004, leaving a legacy buried in Franklin County.

Their son, Roy Winston Freeman Sr., enlisted in the U.S. Army in 1961 amid the Berlin Crisis.

Training at Fort Benning, he earned Airborne jump wings and deployed to Germany, serving honorably until discharge.

Back in Mississippi, he retired from Magnolia Marine Transport (a subsidiary of Ergon), became a farmer, and raised his son (Roy Jr.).

Roy Sr. briefly partnered in business with his son (Roy Jr.) before retiring to Colombia, South America with his wife Gloria, where he passed away in 2020 at 76 years old.

The Modern Freeman Family Era: Roy Winston Freeman Jr. and the Next Generation

Roy Winston Freeman Jr. (born July 16, 1985, in Mississippi) graduated from West Lincoln High School with honors. Inspired by his father’s service and a childhood experience witnessing paramedics save his father’s life during a heart attack, he became an Army medic and earned an EMT certification from Jones College.

Enlisting in the U.S. Army post-9/11 at age 17, he rose to Staff Sergeant, serving two combat tours in Iraq as an infantry combat medic, senior IT NCO, and operations NCO. Decorated with the Combat Medical Badge and Army Commendation Medal, he retired in 2018.

Transitioning to entrepreneurship, Roy Jr. founded Flamsal Group LLC (formerly Dixy Co. LLC) in 2019, expanding into investments and algorithmic trading by 2021. In 2026, he established ARFFO LLC as the family’s single-family office, headquartered in Mississippi and domiciled in Wyoming, managing assets and subsidiaries like The Roy Freeman Company (via Roy Freeman Holdings LLC). As Executive Chairman of Freeman HoldCo LLC, he oversees a diverse portfolio in real estate, goods and services, and philanthropy.

Married to Ashley L. Freeman, Roy Jr. is father to four sons: Trace Freeman, Jon Thomas Freeman, Kade Whitworth, and Samuel Jay Freeman. Pursuing an Associate of Science in Business from Columbia Southern University (expected 2026), he balances family with passions like Alabama and New Orleans Saints football. Through the Freeman Empire Impact, the family emphasizes education, community development, and public policy.

A Unified Legacy

Roy created Freeman Pillars, a comprehensive framework designed to guide the Freeman family in building enduring strength and unity across generations through four core pillars: Family, Legacy, Wealth, and Impact. This blueprint draws from proven multi-generational models to foster intentional governance, long-term planning, and purposeful philanthropy, ensuring our shared values and assets thrive amidst growing complexity.

From Henry Freeman’s colonial arrival to Joseph Benjamin Lewis’s Revolutionary valor, and through Mississippi’s farming generations to today’s global enterprises, the Freeman family exemplifies American progress. United by heroic patriotism—spanning the Revolution to post-9/11 conflicts—we celebrate our heritage while building for the future.

Additional Freeman Family genealogical information may be found here.