Christ Church Cemetery

Discover the Legacy of Sydney Smith Lee: Celebrated Naval Officer and Brother of Robert E. Lee

Early Naval Career and Service

Sydney Smith Lee (September 2, 1802 – July 22, 1869) was a member of the Lee Family and is buried in Christ Church Cemetery, along with twenty-six other individuals with the Lee surname. He was the older brother of Robert E. Lee (January 19, 1807 – October 12, 1870). Sydney’s legacy includes his service as a United States naval officer. One of his key achievements was commanding the USS Mississippi (1841), a paddle frigate that served as the flagship of Commodore Matthew C. Perry during his significant mission to open Japan in 1853. Additionally, on March 24, 1847, Sydney was ordered off the USS Mississippi to command a 24-pounder during the siege of Veracruz in the Mexican War. His brother Robert E. Lee joined him, serving in the United States Army.

In 1860, the first official Japanese Embassy arrived in the United States, traveling from San Francisco to Washington D.C. This mission was initiated by Japan’s Tokugawa government to present treaty ratifications based on 1858 agreements. These agreements were made between Townsend Harris, the first American ambassador to Japan, and the Japanese government. The delegation’s journey involved traveling aboard the Powhatan to Panama, crossing the Isthmus by train, and then heading to Washington, D.C.

Sydney Smith Lee played a significant role during this period. As documented by Dallas Finn in “Guest of the Nation: The Japanese Delegation to the Buchanan White House,” Lee was among a group of Naval officers chosen to escort the Japanese delegation. This account was published in White House History, Number Twelve, Winter 2003, by the White House Historical Association, Washington, D.C., on page 20.

Lee was joined by two officers: Captain Samuel Francis Du Pont, a hero of the Mexican War, and David Dixon Porter, an officer praised by Commodore Perry who was later buried at Arlington National Cemetery. This trio guided the Japanese delegation through the official ceremonies in Washington. Their journey included several events, including a reception in the East Room of the White House on May 17, 1860.

At this event, President Buchanan, his cabinet, and other attendees greeted the Japanese delegates. Due to the linguistic barrier – the Japanese delegates knew only Dutch among Western languages – interactions were facilitated by translating from Japanese Dutch to American English and back.

The visit, from their arrival in San Francisco to their engagements in Washington D.C., highlighted the importance of international diplomacy and the efforts of both nations to build a relationship. At the end of June, the Japanese delegation returned to Japan.

In a captivating photograph by Mathew Brady, Captain Du Pont is seated at the center, commanding the commission responsible for escorting the Japanese delegation during their visit in 1860. Commander Sydney Smith Lee is flanking him on the left, while on the right stands Lt. David D. Porter—image courtesy of the White House Historical Association.

Civil War Allegiances

In April 1861, following Virginia’s secession declaration, he decided to resign from his post, and on April 22nd, he was officially dismissed. Coincidentally, on the same day, his brother, Robert E. Lee, assumed command of all the Commonwealth of Virginia’s forces. Subsequently, he received a commission as a Commander in the Confederate Navy and was entrusted with the leadership of the Gosport Navy Yard. Under his guidance, the charred remains of the USS Merrimack were skillfully transformed into the formidable ironclad warship known as the CSS Virginia.

 Louis Prang & Co. of Boston crafted a striking chromolithograph titled “The Monitor and Merrimac: The First Fight Between Ironclads,” portraying the epic Battle of Hampton Roads.

In May 1862, Lee assumed control of Drewry’s Bluff, a strategic 90-foot high bluff on the James River, about seven miles south of Richmond. This location, notable for a sharp bend in the river, made it an excellent choice for defense. On May 15, 1862, during a fierce bombardment by five Union gunboats, including the renowned USS Monitor, both his brother Robert E. Lee and Jefferson Davis, the President of the Confederate States of America, were present. The fort withstood the intense five-hour battle and successfully held its ground.

Over the subsequent two years, Lee dedicated his efforts to fortifying and enhancing the defenses of Drewry’s Bluff, transforming it into a robust stronghold. Additionally, he employed the site as a training ground for the Confederate Navy Academy, preparing naval forces for their crucial roles in the ongoing conflict.

In Drewry’s Bluff, Virginia, a formidable Columbiad gun commands attention from within Fort Darling, steadfastly guarding the James River. This historical image can be found in the Library of Congress archives.

Personal Perspectives on the War

In 1863, Lee expressed strong disapproval of South Carolina’s actions that led the South into the complexities of secession. He voiced his frustration, even suggesting they should be “hanged” for their role. He also lamented his desire to remain in the old navy, implying that he regrets leaving his previous naval career.

The obelisk honoring Sydney Smith Lee and Anna Maria Mason stands gracefully in Christ Church Cemetery, Wilkes Street Complex, Alexandria, VA. Behind the memorial, a proud flag unfurls in the Alexandria National Cemetery, the second oldest federal cemetery, established in 1862 as the solemn resting place for courageous Union soldiers who bravely fell during the American Civil War.
to the memory of
Born Sept. 2, 1801
Died July 22, 1869
Blessed are the pure in heart
for they shall see God
The first panel on Lee’s obelisk
to the memory of
wife of
Commodore S.S. LEE
Born Feb. 26, 1811
Died November. 3, 1898
He giveth His beloved sleep
The second panel on Lee’s obelisk

Later Life and Burial

After the Civil War, Sydney Smith Lee tried his hand at farming at Smithland Plantation in Stafford County, Virginia, but was unsuccessful. His interactions with his younger brother, Robert E. Lee, were rare. They last saw each other on May 6, 1869, when they attended services together at Christ Church in Alexandria, Virginia. Unfortunately, Sydney passed away just a few months later, on July 22, 1869. General Lee arrived in Alexandria on July 24, 1869, two days too late to attend his brother’s funeral.

Family Connections

In 1834, Smith tied the knot with Anna Maria Mason Lee, affectionately known as “Nannie” (February 26, 1811 – November 3, 1898), who happened to be the sister of James Murray Mason, who is also buried in Christ Church Episcopal Cemetery. The couple was blessed with seven children, among them Fitzhugh Lee, who later became a prominent figure as a former Confederate general and the 40th Governor of Virginia from 1886 to 1890. Another notable child was Captain Sydney Smith Lee, Jr. (February 10, 1837 – April 15, 1888).

Anna Maria Mason Lee (1811 – 1898) is depicted in a captivating oil on canvas portrait created around 1830 by the skilled artist John Eagle (1796 – 1865). Notably, John Eagle was the son-in-law and protege of the renowned painter Thomas Sully. Today, the original portrait is proudly exhibited at the Stratford Hall museum in Westmoreland County, Virginia, as part of the enthralling display titled “Stratford at the Crossroads: Atlantic Cultures & The Creation of America.”

Syndey Smith Lee, Jr.

Following his father’s footsteps, Lee Jr. served in the Confederate Navy, actively participating in various naval battles. He was part of the crew of CSS Louisiana in 1862 and later contributed to the missions of CSS Atlanta and Georgia from 1862 to 1864. He also saw action on CSS Rappahannock near France in 1864 and later served on CSS Shenandoah from October 1864 to November 1865. When the CSS Shenandoah finally struck her colors in Liverpool, England, on November 6, 1865, as she surrendered to British authorities, it marked the last formal surrender of Confederate forces at the end of the American Civil War.

Destruction of Whale Ships off Cape Thaddeus Arctic Ocean June 23, 1865, by the Conft Stmr Shenandoah” Colored lithograph of artwork by B. Russell, depicting CSS Shenandoah’s assault on the U.S. whale ships in the Bering Sea area. Individual items shown are (from left to right): brig Susan Abigail (burning); ship Euphrates (burning–distant); CSS Shenandoah; ship Jerah Swift (burning–distant); ship William Thompson (burning–distant); ship Sophia Thornton (burning); whaleboat going to warn other whalers (very distant); ship Milo which carried the destroyed vessels’ crews to San Francisco; ice in the distance. Collection of President Franklin D. Roosevelt. U.S. Naval Historical Center Photograph

After the war, Lee Jr. ventured into farming in Argentina, leading a solitary life as he never married. In 1888, he passed away and was laid to rest near his parents’ resting place.

In memory of
Capt. S.S. Lee
son of
Commodore S.S. & A.M. LEE
born 1837
died 1888
Simply to Thy cross I cling.
Lot 20:7

Nannie, or Anna Maria, lived a full life until 1898 and now rests in eternal peace beside her beloved husband in Lot 20:5. A dignified obelisk adorned with place stones bearing the initials “S.S.L.” and “A.M.L.” serves as a poignant marker, commemorating their final resting place.

Sources of Information

Lee, C. G., Jr. (1957). Lee Chronicle: Studies of the Early Generations of the Lees of Virginia. Thomson-Shore. Published for The Society of the Lees of Virginia.

Pippenger, W. E. (1992). Tombstone Inscriptions of Alexandria, VA (Volume 3). Family Line Publications: Westminster, Maryland.

Johnson, A. E. (1994, July). Handsomest Man in the Confederacy. American Civil War.

Finn, D. (2003). Guest of the Nation: The Japanese Delegation to the Buchanan White House. White House History, (12). White House Historical Association.

Hakenson, D. C. (2011). This Forgotten Land Volume II: Biographical Sketches of Confederate Veterans Buried in Alexandria, Virginia. Donald Hakenson.

Cole, R. (2019). Light-Horse Harry Lee: The Rise and Fall of a Revolutionary Hero. Regnery History.

Connolly, A. (Curator) & Deetz, K. (Director). Stratford at the Crossroads: Atlantic Cultures & The Creation of America. Stratford Hall. Home of the Lees of Virginia. Stratford, VA.

United States National Park Service. (n.d.). Richmond Battlegrounds, Drewry’s Bluff. The official website of the United States National Park Service. Retrieved in 2023 from: []

Gunston Hall. (n.d.). George Mason’s Descendants. Retrieved from

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By David

As a public historian, I am dedicated to preserving and sharing the rich history of Alexandria, Virginia, and the surrounding region. With a deep passion for bringing the past to life, I serve my community in this meaningful role.

Before this, I enjoyed a fulfilling career as a businessman and entrepreneur. Now retired, I have found a new sense of purpose in my work as a public historian.

Since 2015, I have had the privilege of serving as the Superintendent of the historic Presbyterian Cemetery and Columbarium, located within the Wilkes Street Cemetery Complex in Alexandria. This cemetery holds a special place in my family's history, as it was started in the early 1800s by the Old Presbyterian Meeting House, a historic congregation dating back to 1772 that is situated one mile east in the heart of Old Town. The cemetery is the final resting place of my parents, and the Meeting House is where I have worshipped for over 60 years.

As a public historian, I am thrilled to lead tours of the Wilkes Street Cemetery, which has thirteen cemeteries in a complex with over 35,000 interments. It is considered the most historic cluster of cemeteries in the United States. These sacred grounds offer a fascinating glimpse into the story of Alexandria and its people. I also enjoy guiding tours of nearby Civil War battlefields, combining my passion for history with the compelling narratives of those who fought and fell on these hallowed grounds, bringing their stories to life. I primarily lead tours of Harpers Ferry, South Mountain, and the Antietam Battlefields, along with tracing the footsteps of those involved in the Assassination of President Abraham Lincoln in April 1865. I am also a licensed tour guide in Washington, D.C.

To further engage the community, I manage a blog focused on Alexandria's cemeteries, where the many souls buried across the city are memorialized. I am also an active Board Member of the Alexandria Historical Society and the Lee-Fendall House Museum.

Whether you are a resident or a visitor to the area, I invite you to explore Alexandria's rich history by joining one of my cemetery or battlefield tours, reading my blog, or connecting with me on social media. It is my sincere pleasure to bring the city's captivating past to life and serve my community meaningfully.

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