Robert Lindsay Sinclair, Sr.

Bob Sinclair, Sr., dynamic husband, father, and longtime leader of the family’s radio broadcasting business passed away peacefully on April 20, 2025. Bob was born in Charleston, West Virginia on May 31, 1945 to John and Virginia Sinclair and was the oldest of three, growing up with a younger brother David and sister Ann. With a drive to explore new opportunities, he left West Virginia to attend Harvard University where he studied History, a subject that perfectly matched his immense curiosity about the world.

Bob joined the company founded by his father in the late 1960s and played a central role in its growth. Under his leadership, Sinclair Communications expanded from a small collection of radio stations into a broad portfolio of stations, growing Sinclair Communications from one station, Honey Radio, in Norfolk to five stations (WNIS, Bob FM, US 106.1, 96X, and WTAR) as well as multiple other stations at various times in Richmond, Honolulu, Santa Rosa, and nine stations in Austin (KLBJ-AM, KLBJ-FM, 101X, BOB FM, La Z 107.1, ESPN 102.7, Latino 97.1, VIBE 93.3, and KGSR). Today, the company continues to operate in Norfolk and Austin.

Bob was bold in his business decisions—often pursuing unconventional paths—and never shied away from risk when he believed in the opportunity. Despite having radio stations in several states, his influence remained strong in the company’s direction and continued success. Those who knew Bob understood how deeply invested he was in the day-to-day operations of the business—never more than a phone call away from weighing in on song choices, formats, or programming decisions. Bob loved the radio industry and was always grateful for the efforts and dedication of all the people in the organization, whether they worked in Austin or Norfolk. Much of the staff in both markets began their careers at the stations and have worked for the company for decades, a reflection of the loyalty and family-like culture Bob helped foster.

Outside of work, Bob was passionate about travel and made it a central part of his life. By multiple measures, he was a “citizen of the world”, having visited more than 100 countries, all seven continents, and publishing a book on some of his favorite destinations, Around the World in 80 Minutes. He instilled that same curiosity and appreciation for world travel in his children and in his wife, Lisa with whom he traveled often, always eager to discover new destinations, adding to his ‘top five favorite places’ list.

He also had a deep love for golf, having first played on his high school and college teams, and spent decades playing some of the most iconic and remote courses around the globe during his travels to far flung places. A member of Cedar Point Golf Club in Virginia and Lost Pines Golf Club in Texas, he loved playing golf with Lisa.

With a razor-sharp mind and a sharp wit to match, Bob was a natural storyteller—able to hold a room with stories that were equal parts provocative and entertaining. Whether recalling business deals, off the beaten path adventures, or debating ideas, his perspectives always sparked conversation and left an impression, whether you agreed with him or not. A member of Mensa, he was always eager to engage in thoughtful, challenging conversations, and was a formidable Trivial Pursuit player. He was a strong presence in any room, but his affection for his dogs showed a softer, more tender part of who he was. Bob was smart, bold, and full of energy right up until the end. Bob was truly one of a kind. He will be missed by many.

Bob is survived by his wife Lisa Heath; his children, Samantha and son-in-law Kevin Trainum; Sherry Kistler; Stacey Sinclair and son-in-law Gerald Monk; Bob Sinclair, Jr. and daughter-in-law Kristi Sinclair; stepdaughter Bailey Heath, as well as eight grandchildren, Katie, John, Anna, Will, Anna, Ben, Kennedy and Bobby.

Bob's life will be celebrated by family and friends in a private gathering in June. Those wishing to send condolences or receive more information may contact the family directly. In lieu of flowers or a memorial donation, friends and loved ones are encouraged instead to spend it on travel—to take a trip and explore the world, something Bob would have appreciated.