The Annie Oakley pamphlet arrived and the tissue guard is definitely the original. It is sized to the pamphlet on three sides, slightly longer on one end.
I've tried to locate information about these, the cover photo is from 1880s and the drawing on the reverse of her shooting from a bicycle probably dates to the 1890s when bicycling was all the rage. The only clues in the pamphlet are that she states that she has traveled in 14 countries and hunted in almost all of them. This sounds to me like her traveling days or over at the point when the pamphlet was printed. She also states "To me, the use of a cheap gun is like driving Star Pointer with a clothes line- you never know when the line is going to give way." I looked up Star Pointer and he was a race horse, the first Standardbred to break the two minute mile. Here is the info on Star Pointer:
"Star Pointer was the first Standardbred race horse to complete a mile in less than two minutes. Bred in 1889, he was a pacer by Brown Hal out of Sweepstakes.
Driven by David J. McClary, Star Pointer began racing in 1894 and in 1897 lowered the record for the mile to 1:59¼. His record stood until 1903, when it was lowered to 1:59 by Dan Patch.
Star Pointer was bred by Captain Henry P. Pointer of Spring Hill, Tennessee. His sire was Brown Hal and his dam was Sweepstakes. He broke the 2 minute mile barrier on August 28, 1897 at around 4:00 pm with quarter times of 30 sec, 293⁄4, 291⁄4, 301⁄4 for a 1:591⁄4 time.
Star Pointer died of a stroke several weeks before the Christmas of 1910. His record was 22 victories and 4 seconds in 30 starts. He had a total of 60 wins in 79 heats and earnings of over $50,000. Star Pointer's remains were buried beneath the finish line of the Dean Racetrack in Palatine, IL but his remains are now lost to history.
Star Pointer was owned by James A. Murphy,(born in Rome New York August 11, 1846 and died January 24, 1920 in New York City)and was a resident of Chicago Illinois. He was famous throughout the United States as a thorough horseman and was a familiar figure on the tracks of the big meets. James A. Murphy organized the Central Grange and Stock Exchange. Utica Saturday Globe January 24, 1920 Obituary."
So in the day that this pamphlet was written, Star Pointer was a common household name and everyone would have understood the reference. Annie toured with Buffalo Bill's Wild West Show from 1885 until 1902. She also performed in other shows on the side for extra income. In the pamphlet she also mentions Schultze Smokeless Powder, which was in common use throughout the time that she was performing.
https://en.wikipedia.org/wiki/Annie_OakleySo my estimate is that the pamphlet dates from 1890s until the early 1900s. Does that sound about right to you guys? Any thoughts?