Appalachian Figures
On a summer weekend in the southern Chesapeake, sailboats race across the bay for the Leo Wardrup Memorial Cape Charles Cup, a two day regatta that has become one of the big social events of the Broad Bay Sailing Association calendar.
For people in Virginia Beach, the Wardrup name belongs to a retired Navy captain, long serving Republican delegate, and passionate sailor. For people in Middlesboro, Kentucky, it belongs to a Bell County meat packing family and to a boy born under Cumberland Gap who would carry an Appalachian hometown into a very different political and maritime world. Modern reference works on Middlesboro list him among the town’s notable natives, a reminder that not every Appalachian story stays in the hills.
This article follows Leo Clyde Wardrup Jr. from the streets and cemeteries of Middlesboro to Navy registers, committee rooms in Richmond, and finally to a race that still sends boats eastward toward Cape Charles in his name.
A Bell County boy in a meat packing family
Genealogical records place Leo Clyde Wardrup Jr.’s birth on September 5, 1936, in Middlesboro, Bell County, Kentucky, the son of Leo Clyde Wardrup Sr. and Kathryn (or Katherine) Callison Wardrup. FamilySearch trees for his mother, Kathryn E. Callison, and for his sister Mary Kathryn Wardrup, along with his own memorial entries, tie the family firmly to Middlesboro in the 1930s and 1940s and list siblings such as Mary Kathryn, Thomas, and Virginia.
The Wardrups were not coal operators or courthouse lawyers. They were meat packers. A mid twentieth century piece in The Mountain Eagle, looking back on local industry, describes how a member of the Wardrup family operated a liverwurst business in Middlesboro before moving to Harlan in 1933 to start the Wardrup Provision Company. A 1954 accident story in the Floyd County Times mentions “Mr. Wardrup” of the Wardrup Provision Company of Middlesboro driving through eastern Kentucky, placing the firm and its proprietors squarely in the regional network of small packing and provision houses that supplied butcher shops and groceries across the mountains.
Taken together, those sources sketch a familiar Appalachian trajectory. In the hard years between the Depression and the Second World War, the elder Leo Wardrup and his relatives built a business that turned hogs and cattle into paychecks. Their children grew up in a small industrial town laid out in the nineteenth century as a speculative “Pittsburg of the South,” now weathering booms and busts in coal, rail traffic, and wartime demand.
Graveyard and cemetery records reinforce that picture. The FindAGrave memorial for Leo Jr. identifies his parents as Leo C. Wardrup and Kathryn Callison Wardrup and links him to siblings Mary Kathryn, Thomas, and Virginia, several of whom are buried back in Bell County. Other Wardrup relatives appear in Middlesboro cemetery transcripts, anchoring the family in local soil even as later generations scattered.
From Middlesboro High to Chapel Hill
Obituaries and legislative memorials agree that Leo Jr. came of age in Bell County schools before leaving the mountains for a wider world. He attended Middlesboro High School and then Castle Heights Military Academy in Lebanon, Tennessee, a path that combined local public education with a more regimented prep school environment popular among Southern families grooming sons for college or military service.
From there he went to the University of North Carolina at Chapel Hill, where he completed a business degree in the 1950s. Contemporary biographical sketches from the Virginia House of Delegates history project and later obituaries note that he stayed on as an instructor at UNC for a short period, an early taste of teaching that would resurface decades later when he served as an adjunct professor at Old Dominion University in Norfolk.
The combination is characteristic of a certain mid century Appalachian story. A young man born in a small commercial town on the Kentucky side of Cumberland Gap uses a regional business school degree and military prep training to step onto a national officer track. The route out of the mountains runs, in his case, through Chapel Hill and then straight into the Cold War Navy.
Twenty eight years in the United States Navy
According to both his obituary and legislative biographies, Wardrup entered the United States Navy in 1958 and served until 1986, a twenty eight year career that saw him rise from junior officer to captain in the Supply Corps.
Official Navy registers and the Annual Register of the United States Naval Academy from the early 1960s list “LT Leo C. Wardrup Jr.” among the officers on duty, evidence that he belonged to the cadre of Supply Corps officers who kept ships, bases, and schools functioning during the height of the Cold War. Those registers, like most federal publications of the era, are dry rosters of names and billets, but they fix him in time as part of an institution that was expanding rapidly and sending young officers into a global network of shipyards, depots, and war zones.
Later biographical summaries and the 2014 House Joint Resolution honoring his life describe a varied career that included sea duty, service in Vietnam, and stateside positions in acquisition and systems commands. They credit him with major decorations such as the Meritorious Service Medal and emphasize that he retired as a captain, the senior rank for most non flag officers.
Just as important to his later political style, those same sources note his experience teaching logistics and management topics for the Navy and for civilian universities. By the time he hung up his uniform in 1986 and settled in Virginia Beach, he had spent nearly three decades in an institution that rewarded careful preparation, an eye for budgets, and an ability to navigate hierarchy.
A Virginia Beach delegate with an Appalachian birthplace
After the Navy, Wardrup moved into consulting and part time teaching in the Hampton Roads area, then into electoral politics. The official History of the Virginia House of Delegates identifies him as the Republican member for the 83rd District, based in Virginia Beach, first elected in 1991 and seated in January 1992. He would hold that seat through the 2008 session, representing a strip of coastal and suburban neighborhoods far from the Appalachian ridges where he was born.
House records and later summaries agree that he quickly became associated with transportation policy. He served on the Transportation Committee, eventually chairing it, and sat on powerful panels such as Appropriations, where his background in budgeting and logistics made him a natural fit.
Issue scorecards and bill tracking sites fill in some of the detail beneath those titles. The Virginia League of Conservation Voters’ 2006 Conservation Scorecard, for example, discusses House Bill 665 on billboard vegetation control and identifies Wardrup as its patron, an example of how his transportation agenda often intersected with questions about roadsides, development, and the environment.
Legislative audit reports from the Joint Legislative Audit and Review Commission list him among the commission’s members on studies ranging from homeland security funding to assisted living facility regulation, placing him in the thick of early twenty first century debates about how Virginia spent federal counterterrorism money and how it oversaw a rapidly growing assisted living industry.
A 2007 opinion from the Office of the Attorney General, issued in response to a request from “The Honorable Leo C. Wardrup Jr., Member, House of Delegates,” addresses whether a corporation in which he was a principal could hold certain types of alcohol licenses. The opinion’s dry language offers a glimpse of the knots that citizen legislators often face when their private business ties intersect with heavily regulated sectors like alcohol and transportation.
Campaigns, cards, and committee rooms
Newspaper coverage from the mid 1990s paints Wardrup as a lawmaker who initially struggled against the anonymity of a large legislative body. A Virginian Pilot feature on “Scenes of change from Va. legislature” described him handing out business cards around the Capitol as a new delegate, trying to make sure people could match his name to a face and a district.
A decade later, a piece in the Virginia Capitol Connections / DBAVA newsletter quoted retired Delegate Wardrup reflecting on how he ran campaigns in Virginia Beach. He stressed shoe leather politics, talking about walking precincts, knocking on doors, and relying on volunteers to carry his message across sprawling suburban neighborhoods. That recollection is one of the few first person accounts we have of his views on campaigning. It fits what colleagues and reporters said about him in obituaries and tributes, which emphasized a reputation for preparation, attention to detail, and a willingness to immerse himself in the slow work of committee hearings rather than chasing headlines.
Vote tracking sites such as Project Vote Smart and legislative archives show a voting record that lined up with mainstream Virginia Beach Republican positions of the 1990s and 2000s on taxes, business regulation, and social issues, while also reflecting his particular interest in roads, bridges, and ports. Those patterns help explain why he repeatedly won reelection in a district that was growing rapidly and grappling with traffic, sprawl, and the costs of maintaining infrastructure in a coastal city.
Sailing the bay: the Cape Charles Cup
If naval registers and House roll calls show Wardrup as officer and legislator, sailing logs and race programs show another dimension of his life. Obituaries published in the Virginian Pilot and on Legacy, along with the Hollomon Brown Funeral Home notice, all highlight his love of sailing on the Chesapeake Bay. They credit him as a driving force behind the creation of the Cape Charles Cup, a distance race that sends cruising and racing boats from the lower bay to Cape Charles on the Eastern Shore and back.
Today the Broad Bay Sailing Association runs the event under the official name Leo Wardrup Memorial Cape Charles Cup. Race descriptions on the BBSA site and related event pages explain that the Cup is a two day race with an overnight stay at Cape Charles, drawing boats from across the southern bay and forming part of the Southern Bay Distance Racing Series.
Sailing media pieces and club histories remember Wardrup as skipper of the boat Black Widow, which became a familiar name on Cape Charles Cup results sheets. Coverage in Chesapeake Bay Magazine and in North Sails’ event spotlight on the 2020 Cape Charles Cup emphasizes that the regatta’s renaming in his honor recognized both his racing success and his behind the scenes work to build a friendly, accessible event for cruisers and racers alike.
The 2014 House Joint Resolution celebrating his life makes the connection official. It not only recounts his military and legislative service but also notes the renaming of the Cape Charles Cup as the “Leo Wardrup Memorial Cape Charles Cup,” folding his identity as sailor into the commonwealth’s formal record of gratitude.
Middlesboro in the story
It would be easy to tell Wardrup’s story as purely a Virginia Beach tale. That is how many obituaries and sailing pieces frame it, because that is where he built his career and where he died in 2014 after a struggle with metastatic melanoma.
Yet the documentary breadcrumbs keep leading back to the Kentucky side of Cumberland Gap. Middlesboro appears again and again in genealogical entries, cemetery records, and biographical notes, not only as his birthplace but as the home of the meat packing business that supported his parents and siblings.
The city itself, tucked in a meteor formed basin and long marketed as a planned industrial town, has produced miners, preachers, snake handling Pentecostal pastors, musicians, and, as lists of notable residents now remind us, at least one Navy captain who ended up shaping transportation policy in another state.
In that sense, Wardrup’s life fits a larger Appalachian pattern. In the twentieth century, families across eastern Kentucky and the wider region saw sons and daughters leave for service academies, coastal bases, and Sunbelt suburbs, then reappear decades later in congressional biographies, corporate board lists, or, in this case, the history of a state legislature and the program for a Chesapeake Bay regatta. Their roots remained in mountain cemeteries and small town business ledgers, even as their adult lives unfolded under very different skies.
Why Leo Wardrup belongs in Appalachian history
For a site focused on Appalachian history, it might seem odd to spend so much time on a Virginia Beach delegate whose most visible legacy rides on sailboats in the lower Chesapeake. The archival record suggests otherwise.
Primary sources tie Wardrup unmistakably to Middlesboro and to a family that made its living in the food economy of the southeastern Kentucky coalfield. Navy registers and obituaries document how a young man from that background spent nearly three decades as a Supply Corps officer in a global Cold War fleet. House histories, joint resolutions, attorney general opinions, and audit reports show how he then spent another sixteen years in Richmond working on transportation, regulation, and oversight. Sailing club histories finally place his name on a race that continues to draw people to the water each summer.
Seen together, those layers turn what could be a simple biography into an Appalachian story about mobility, service, and the long reach of small places. A boy born in a Bell County packing house family grew into a figure whose life touched the Navy, the Virginia House of Delegates, and the sailing culture of the Chesapeake Bay, all while carrying a Kentucky birthplace that still appears in the fine print of obituaries, legislative resolutions, and lists of Middlesboro’s notable sons.
Sources and further reading
House Joint Resolution No. 5216 (2014 Special Session I), “Celebrating the life of the Honorable Leo Clyde Wardrup Jr.,” Virginia General Assembly.
Hollomon Brown Funeral Home, obituary for Leo Clyde Wardrup Jr.; Virginian Pilot obituary as preserved on Legacy.com and related memorial sites, including Tribute Archive. Virginia Attorney General’s Office
“Leo Wardrup,” Wikipedia entry, with basic biographical overview of his naval and legislative career; “History of the Virginia House of Delegates – Leo C. Wardrup Jr.,” member biography from the House of Delegates history project. LIS+1
FindAGrave memorial for Leo Clyde Wardrup Jr., including linked memorials for Mary Kathryn Wardrup Bellairs, Thomas Robinson Wardrup, and Virginia Wardrup Rissling; FamilySearch entries for Kathryn E. Callison and Mary Kathryn Wardrup, summarizing the Wardrup family’s presence in Middlesboro and Bell County in the mid twentieth century. Find A Grave+2FamilySearch+2
“The meat packing plant that once hired 50 here,” The Mountain Eagle, 2016, on the Wardrup Provision Company and its move from Middlesboro to Harlan; Floyd County Times coverage of a 1954 accident involving “Mr. Wardrup of the Wardrup Provision Company of Middlesboro,” illustrating the company’s regional footprint. The Mountain Eagle+1
Virginia League of Conservation Voters, Virginia General Assembly Conservation Scorecard, 2006, including discussion of HB 665 (billboard vegetation control) and Wardrup’s conservation voting record. Virginia LCV
Broad Bay Sailing Association, official pages for the Leo Wardrup Memorial Cape Charles Cup; Chesapeake Bay Magazine coverage of the Cape Charles Cup; North Sails “Event Spotlight: Leo Wardrup Cape Charles Cup 2020”; SpinSheet and other regional sailing media on the regatta and its history. SpinSheet+3Broad Bay Sailing Association+3Chesapeake Bay Magazine+3
“List of people from Middlesboro, Kentucky,” and “Middlesboro, Kentucky,” Wikipedia and related educational summaries, for place context and local recognition of Wardrup as a notable native. FamousFix
Project Vote Smart profile and key votes pages for Leo C. Wardrup Jr.; bill tracking resources such as TrackBill and the Virginia General Assembly Legislative Information System, for his voting record and bill patronage. ashe.pro