“I developed a love affair for this bike. I just liked it. It became a member of the family, and you don’t sell a member of the family.”
— Bob Stieg, owner of Annie, a 1934 Harley-Davidson VLD, since 1938

There are conflicting stories on how Bob Steig's 1934 Harley-Davidson VLD came to be named Annie. Bob claims she was named after Little Orphan Annie, who was always optimistic and never gave up even when the going got rough. His wife, Jane, always thought it was named after the neighborhood glamour girl, Annabell “Annie” Lee. However this 74 cubic-inch Flathead twin got its name, she’s had it for a very long time.

Famous beginnings
Before Annie came to live in Bob’s garage, and when she was still very new, she had a moment of glory as the winner of the 1934 Jack Pine Endurance Run, with Fond Du Lac, Wis., Harley-Davidson dealer and rider Ray Tursky taking her to a first place finish.

This was no small deal, because in its day the Jack Pine was the offroad race to win, a three-day, 500-mile offroad event where competitors bashed their way through the deep woods of Michigan’s Upper Peninsula, fording rivers, climbing hills and running through mud, sand and every other type of terrain imaginable, all at an average speed of 24mph. In 1934, only nine of the 87 starters finished the event, run over clay roads made almost impassable by rain. Harley promoted Tursky to the Madison, Wis., dealership as a reward for his widely reported win.

Notably, the factory-supplied saddle bags Tursky used in the 1934 Jack Pine race (a $4.95 option) are still on the bike today.

Following his win, Tursky sold Annie to a Madison police officer, who traded her in the next year. In May 1937, Tursky re-sold the bike, this time to Bernard Stieg, an engineering major in his junior year at the University of Wisconsin. Bernard in turn sold the Harley to his younger brother, Bob (also majoring in engineering), in September 1938.

Although he was only 20 years old, Bob was no stranger to riding. “I started riding in high school,” Bob says. “I used to fix up old junkers with my brother. Both of us were mechanically inclined. I had a 1928 [Harley-Davidson] JD, which was a lot of work compared to the ‘34, which was a virtually new bike.”

Bernard and Bob had numerous escapades on Annie, including a trip to the Indianapolis Speedway to see the then new 4-wheel-drive racers. There were no interstates back then, and it took the intrepid pair more than eight hours to make the 330-mile trip. They watched the race, and then rode back to school in Madison. Annie was also their regular transportation between college and home in Clinton, Wis., a 150-mile trip each way.

In 1941, Bob and Jane, his girlfriend of four years — and to this day the only woman to ever ride on Annie — married. Setting up home in Wisconsin, the newlyweds stored Annie in Bob’s parents’ garage for the winter. Bob remembers that when he tried to start Annie the next spring, smoke poured out of every exhaust pipe joint. A squirrel had somehow filled the muffler
with butternuts.

Life moved on, as it invariably does. Bob and Jane had two sons, and Annie was soon sporting a sidecar to carry the family when necessary. They took the bike on short rides around the Wisconsin countryside regardless of the season, the kids often getting sidecar rides in the snow, and on occasional longer rides to rallies and events.

In 1968, the Stiegs moved to Pennsylvania and Annie, very much a part of the family, came along. The sidecar, by that time rusty and in need of a full restoration, was sold to a friend. By this time Annie wasn’t looking too good herself and needed a total overhaul. Moving into their new home, Annie was rolled into the garage, where she stayed for several years.