John Robert Lindsay

Jack was born in Washington, DC on October 15, 1939. He is predeceased by his parents, Charles Taliaferro “Tolliver” Lindsay, Sr., and Margaret Cox Lindsay, and his brother Charles T. “Terry” Lindsay, Jr. He was raised on Allan Road in Bethesda, MD. Jack (or “Jackie” at the time) attended Westbrook Elementary School, Western Junior High School, and Bethesda-Chevy Chase High School, as well as the University of North Carolina at Chapel Hill. He graduated from the University of Maryland in 1962 with a degree in Economics.

In 1962, he graduated from U.S. Navy Officer’s Candidate School in Newport, R.I. and served as an officer on the U.S.S. Prairie (AD-15) in the Pacific until 1966. He was later honorably discharged as a Lieutenant in the U.S. Navy Reserve in 1968.

Following his active-duty military service, Jack began working with his father and brother in 1966 at Lindsay Oldsmobile Cadillac in Alexandria, Virginia. The business grew to become one of the leading Cadillac dealerships in the country. As an Alexandria resident during this time, Jack was active in civic and philanthropic causes as President of the American Red Cross of Alexandria and the Kiwanis Club of Alexandria, and served on the board of directors of the Alexandria National Bank.

In 1984, he expanded the family business with the addition of Jack Lindsay Cadillac in Jenkintown, PA. The dealership was recognized with two Cadillac Master Dealer awards during his ownership. He continued his passion for business and charitable pursuits in the Philadelphia area as President of the Auto Dealers Association of Greater Philadelphia, an active member of the Pennsylvania Automomotive Association, and a board member on several civic and Catholic educational boards, including the De Sales School of Theology.

Jack sold the Jenkintown dealership in 1993 following the death of his wife, Melissa Howe Lindsay, of breast cancer in 1992. He devoted himself full time to raising his beloved children, Jennifer and Paul, in Washington, DC. He quickly transitioned into the role of single father and was an enthusiastic cheerleader at every sports and school event, and every life milestone, for his children throughout their lives. In the summers, he was happiest spending time with his family at their home in Northeast Harbor, Maine.

As his children grew, he turned his attention back to entrepreneurial pursuits. An appreciation for antique furniture and design drew him to work at Antique & Contemporary Leasing in Washington DC. He eventually purchased the business in 2005 and sold it in 2015.

In 2007, he married Joan “Cookie” Gregory. They split their time between Vienna, VA and Hilton Head, SC. While on Hilton Head, Jack enjoyed golf, biking, spending time on the beach, and hosting family and friends at his home. Additionally, Jack helped serve the community for several years through his work with Meals on Wheels.

A committed Catholic, Jack was more recently a regular communicant at St. John Neumann Church in Reston, VA, St. Ann Catholic Church in Washington, DC, and St. Francis by the Sea Catholic Church in Hilton Head, SC, among many other parishes throughout his life.

Jack was a lifelong golfer and proud member of Washington Golf & Country Club (Arlington, VA), as well as Sea Pines Country Club (Hilton Head, SC).

He is survived by his second wife of 17 years, Joan “Cookie” Gregory and his children: Jennifer H. Duffie and Paul A. Lindsay (Autria), along with four grandchildren: John, Luke, Eliza, and Kit. He is also survived by his sister-in-law, Regina (“Jeannie”) Lindsay, and three nephews: Chip Lindsay, Michael Lindsay, and Chris Lindsay. Also surviving are Lauren Gregory Killian, her two children, and Frank Gregory, and his three children.

A Mass of Christian Burial will be held at 10:30 am on Wednesday June 11, 2025, at St. Ann Catholic Church, 4001 Yuma Street NW, Washington, DC 20016. In lieu of flowers, contributions may be made in his honor to Gonzaga College High School, 19 Eye Street, NW Washington, DC and St. Luke Institute, 8380 Colesville Road, Ste 300, Silver Spring, MD.