Joan and Jack Dempsey’s careers took them to exotic locales
Editor’s Note: Cape May County ranks 15th nationwide and first in the state as a second home destination, so this summer the Herald will be periodically featuring stories about interesting second homeowners. If you have the name of someone you would like to nominate, please email editor@cmcherald.com with the reason why and with contact information. This is the sixth in that series.
CAPE MAY – While many people travel as part of their jobs, not everyone gets to represent the United States in intriguing places like the former Soviet republics Kazakhstan and Uzbekistan in central Asia or Azerbaijan, which spans Europe and Asia.
For Joan Dempsey, who has had a second home in Cape May since 2018, however, it was one of the high points during her career serving the country as part of the intelligence community.
“It was fun to represent our country to senior leaders in foreign countries,” she said, “and it was a privilege. It also was challenging at times. I went to many exotic places like Kyrgyzstan and China under the auspices of the government, so it gave me a really unique vantage point. I loved that aspect of my job.”
She also formed many close friendships along the way. “I loved Australia, as an example, and made close friends during my travels there,” she said. “We were able to build deep relationships over mutual interests over the years.”
While she’s lost count of how many countries she visited representing the U.S., she had her share of interesting experiences, such as eating sheep’s eye bowl in Kazakhstan, fermented goat’s milk aged in a cow’s stomach in Uzbekistan and duck’s brains and feet and fish soup with live fish in it while visiting China.
“I didn’t like any of it, but I was determined to get it down and keep it down,” she recalled.
Dempsey would often come to Cape May to get away from the hustle and bustle of government jobs she and her husband, Jack, had in the Washington, D.C.-Virginia area. She has 25 years of experience working with the federal government and 17 years working as a senior civilian in the Department of Defense. She now is semiretired, serving on three corporate boards and three advisory boards, all in the tech industry.
Her husband has 38 years’ combined government service, retiring as an U.S. naval officer and as a civilian from the Defense Department.
During her career with the federal government, Dempsey held two presidential appointments. In the Clinton administration in 1998, she was the first female appointed by a U.S. president and confirmed by the Senate to one of the top three U.S. intelligence positions as deputy director of Central Intelligence for community management. In the George W. Bush administration, she served as executive director of the president’s Foreign Intelligence Advisory Board.
During her career with the Defense Department, she served as deputy director of intelligence at the Defense Intelligence Agency, as the deputy assistant secretary of defense for intelligence and security, and as the acting assistant secretary of command, control communications and intelligence.
While traveling to some exotic places was among the high points of her career, there were also some low points, as she was challenged at times because she was a female in a very male-dominated environment.
“Believe it or not, some of the western countries were the most challenging,” she said, “but I always knew that I was representing the United States, and there was a demand for respect.
“I didn’t feel like a trailblazer back then because there weren’t very many women in higher positions. I was fortunate to have many men who mentored me along the way. Over time, more women had the opportunity to take advantage of more opportunities.”
Dempsey’s interest in the military and government grew after hearing many stories from her dad, who served in, and eventually retired from, the Navy.
“I went to college for a year, but I was floundering about what I wanted to do, so I joined the Navy,” she said. “I saw that my career in the Navy as a young woman was going to be very different than my dad’s. I loved the service, loved wearing the uniform, and it set me on a path for my career in security and intelligence.”
Both Dempseys have been coming to Cape May since the 1980s, and Joan said, “We always loved it. Some of our friends in the D.C. area had homes in the Cape May area, and we always said once we retired, we’d think about having a home there as well.”
They renovated their first home on Columbia Avenue in Cape May shortly after buying it, and found it “too small almost immediately.” So a year later, they sold it before buying their current home on Hughes Street.
“There have been many changes over the 40 years we’ve been coming here, but one of the big changes is the increased number of and quality of restaurants here,” she said. “There are so many restaurants here that are truly phenomenal and so good.
“Picking a favorite restaurant is tough because there are so many good ones. Jack would pick Lucky Bones because he likes the local vibe there. I like Grana BYOB and Andrea Trattoria Italiana (both in Cape May).
“Cape May is a real community, not a place attached to the ocean. It has performing arts, charities, all sorts of activities. We learned over time that to be successful as a second home, there has to be a community, you have to be part of something. Cape May is a special place.”
The couple are involved with the Mid-Atlantic Center for the Arts, where Joan was a lecturer for the Lessons of History program in 2016. She now serves as part of the team bringing speakers in each fall. They also are involved with the Cape May Community Food Closet, the Naval Air Station Wildwood Aviation Museum, Cold Spring Village and Cape May Stage.
When not in Virginia, where their main residence is, the Dempseys like to walk the beach evenings, as neither are regular daytime beachgoers. Her husband plays tennis daily at the Cape May Tennis Club. They like entertaining friends, and their large front porch is always occupied when they are there.
“When we first started coming here, Cape May was predominately a beach-vacation location,” she said. “Now we feel like there’s a real community here, and we are really blessed.
“As second homeowners, we feel a real obligation to support the community. We’ve made a lot of friends who have made us feel a part of Cape May, and are active and supportive like we are. It’s really a magical place.”
Contact the reporter, Karen Knight, at kknight@cmcherald.com.
