John R. Toole was born in Maine in 1850 and raised in Madison, Wisconsin. While working at the Bonanza Mine in Challis, Idaho in the 1870s, he met and married Anna Hardenbrook. In 1883 the young family moved to Anaconda, Montana, with Anna’s father, Allen Hardenbrook and his wife, Thula. John Toole worked in Marcus Daly’s Anaconda smelter. In 1886 he was elected to the territorial legislature for two terms, and in 1890 he served a term on the state legislature. In 1900 the family moved to Missoula. John Toole went to work for the Big Blackfoot Milling Company where he became president and was heavily involved in timber acquisition.
John R. and Anna Toole had six children: Honora, Thula, Allen, Howard, Brice, and John R., Jr. John R. Toole died in 1916 and Anna Toole died in 1934.
From the guide to the John R. Toole family papers, 1849-1916, (University of Montana--Missoula Maureen and Mike Mansfield Library Archives and Special Collections)