Robert Brookings Smith II, or “Bob,” as he was known to friends and family, was born in 1934 in St. Louis, Missouri, to Katherine “Taffy” and Alan T. Smith. Bob was the youngest of three boys. Bob attended St. Louis Country Day in Ladue, Missouri, The Hotchkiss School in Lakeview, Connecticut, and finally Yale University. After graduating from Yale, he was drafted to serve in the Korean War.

After the war, he traded his Cessna for a DC-3, flying for Republic Airlines, before settling in for a long career as a 737 pilot for United Airlines. While with United, a young red-haired stewardess and model, Kathleen Lally, happened to bring him dinner during a flight. They would continue to dine together for the next 40 years.

Finding a harbor in Annapolis, Maryland, Bob would go on to amass of collection of unseaworthy boats, from Bracer, a Tartan sailboat, to Quoth, a Century Raven, and Bobby Sox, a Century Coronado. Most of these vessels can still be found on the bottom of the Chesapeake Bay. While on dry land, he found time to toil on his invention, the “Leverbike,” a unicycle contraption that nearly maimed several neighborhood test subjects, as well as a detective novel that is widely viewed in literary circles as the most unintentionally funny book ever written.

Following retirement, Bob decided to reef his sails against the cold wind and state income tax and took a southerly course to Amelia Island, Florida. While there, he took up golf with a vengeance, spending tens of dollars on off-brand clubs in a valiant effort to knock his purloined range balls past the ladies’ tee. He was a founding member of the Saturday Morning Old Golfers (the “SMOGS”), a rogue’s gallery perhaps most infamous for always double bogeying the 19th Hole. It was in Florida that he was joined by his beloved dogs Phoebe and Atticus, and later, Cammi, a spaniel who would remain his companion until the end.

In 2010, Bob and Kathleen moved to Savannah, Georgia, to be closer to family and dropped anchor on Isle of Hope. Luckily for Bob, new friends were waiting around the corner at the Driftaway Café, where he earned the moniker “Two Soup Bob,” and was known for wearing a sweater as a cape and for his trademark 5 percent gratuities. And when he found his way to the Marshes, he wasted no time in befriending the entire staff—including his favorite friend and bartender Xavier.

The one waypoint Bob returned to throughout his life was Harbor Springs, Michigan. Spending nearly 85 summers on the shores of Lake Michigan, Bob never missed a party or a sailboat race. His stories and kind heart were always welcome on any porch, as well as his insightful commentary on the old cook’s courage in Gordon Lightfoot’s magnum opus, “The Wreck of the Edmund Fitzgerald,” which could be heard playing from the cottage from June to September.

While yachtsmen of old brought home souvenirs from exotic ports of call, the only thing Bob took from his travels were friends. From St. Louis to Annapolis, from Michigan to Amelia, and from his last berth in Savannah, Bob collected friendships that would last a lifetime. Never one to seek attention for his many generous charitable contributions, they will not be listed here. The only monument Bob would have wanted were his dear friends, steadfastly standing by him to the end.

Bob had four children: Robert III, Christopher, Jonathan, and Molly (Wilson). He also had eight grandchildren: R.B. Smith IV, Alexandra Smith, Finn Smith, Connall Smith, Chloe Smith, J.P. Moccia, Katie Moccia, and David Wilson.

Bob died on October 23, 2021, at the Marshes at Skidaway Island in Savannah, Georgia. He was buried in Harbor Springs, Michigan, next to wife Kathleen.

In 2022, the Georgia Historical Society received notification of a generous bequest left by Bob to the organization. This legacy gift was used to establish the Robert B. Smith II Fund, thereby providing for the mission and work of this historic institution in perpetuity.