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November 1922 - Annie Oakley and her husband Frank Butler took a boat from Boston Massachusetts to Jacksonville, Florida, where they sent their beloved dog, Dave, by train ahead of them to Leesburg, and on Thursday, Nov. 9, they continued their trip with their friends J. J. Stoer and his wife. The Daytona Beach Morning Journal reported the following Saturday that they were in a ”big Cadillac” driven by “a Mr. Young,” the Stoers’ chauffeur, heading south toward Daytona Beach on their way to Leesburg for the winter.

Cadillacs were luxurious even then, and they all came equipped with a powerful V8 engine. The year before this, 1921, two Cadillacs (a sedan and a touring car) had raced in the prestigious Monaco Concours d’Elegance. Touring cars were open-bodied, seating four or more people, and they were especially popular until closed-bodied cars became less expensive during the 1920s. (In 1920 the Cadillac factory in Detroit had 77 buildings and 6,000 employees.)

The 1921 Cadillac models included a seven-passenger touring car, a seven-passenger open car, and a five-passenger sedan. These automobiles sold for as much as $5,090 the same year that the Model T Ford cost $370. For $5,000 in 1921 a person could buy an entire farm. Annie Oakley was riding in style.

Traveling at what must have been a high speed, the Cadillac’s tires likely were growling a whirring noise as they raced over the red bricks of the Dixie Highway about 46 miles north of Daytona Beach when they passed another vehicle and the tires slipped off the bricks into what was likely a soft shoulder alongside the highway, causing the chauffeur to lose control. As he attempted to steer the huge car back onto the bricks, the Cadillac careened into the roadside and “turned turtle,” pinning Annie Oakley under the massive car. The Daytona Beach Morning Journal reported that their car was “forced into the sand by a passing machine” and that Oakley was “in a critical condition.”

Oakley was barely five feet tall, and during most of her years in Buffalo Bill’s Wild West Show she weighed only a little over 100 pounds. The Cadillac, which weighed more than two tons, fractured her hip and right ankle. What may have saved her, though, was that behind their car was a Mr. B. Benson of Fort Pierce who helped free her and drove her hurriedly to Daytona Beach.

There, Oakley was admitted to Dr. Bohannon’s Hospital and Sanitarium, run by respected physician Clyde C. Bohannon. When she was stabilized, her husband went to Leesburg to retrieve their dog, and the husband and dog then rented a room near the hospital.

Dave was a black, tan, and white English setter and was loved by this couple who had no children.

After Oakley recuperated for several weeks through November and December, she was released from Dr. Bohannon’s care. But she was forced to wear a heavy metal brace on her right leg, and she still had to walk with crutches when she, her husband, and their dog finally left Daytona Beach.

Three and a half months after the auto accident, tragedy struck again. A passing car hit Dave on Main Street in front of the Lake View,Hotel in Leesburg and he died on Feb. 25, 1923.

To pay homage to their canine companion, Butler penned a short booklet titled “The Life of Dave as Told by Himself.”

“Dave was more than some humans,” Butler wrote on the back page of the booklet. “He sat for weeks watching faithfully by the bedside of his mistress and would snuggle close, tapping gently with his little paw, his big eyes burning with love.” Dave “awaits us both in the Happy Hunting Ground,” Butler concluded.

The Butlers wished to bury Dave in the city’s Lone Oak Cemetery, but were turned away by officials who said only people could be interned there. Dave’s final resting place was, on property owned by George and Annie Winter, friends of the Butlers.

Leesburg lore maintains that over the next few years, the Butlers rarely left Leesburg. 10 months later on October 8, 1923 in Leesburg, she once again stunned the crowds with her rifle, and although she had to set aside her crutches and stand entirely on her good left leg, she “winged pennies tossed in the air at twenty feet,” and several times she tossed five eggs at once into the air with her left hand and shot every one before it hit the ground.

Sixty-three-year-old Annie Oakley was still the greatest marksman in the world.

Near the library, In Leesburg there is a statue of Annie Oakley and her dog Dave