According to Kay Atwood, “The [Monkey Puzzle tree] seeds were brought to Ashland by Dr. Boslough and given to Lithia Park and several Ashland residents.” I have not seen any clue as to where he got the seeds. The tree at Dr. A. W. Boslough’s house was likely planted in 1913, based upon a 1915 photograph that shows the edge of a small tree at the same spot in the front yard.
The Walk Ashland article provides photos of Boslough's house and various Monkey Trees, with historical information on both.
Notes
Articles by Peter Finkle, on his Walking Ashland website
City
Ashland
Source Reference