Brothers Robert, Ben, and Will Bailey left their home in Dunlap, Kansas and settled in Edmonton in 1910. The following year, each brother started his own homestead in Keystone, Alberta. Will Bailey was married to Matilda and they adopted a son, known to friends and family as “Big Eddy.” Unfortunately, Will Bailey died in the Spanish flu epidemic of 1918, and his wife later married Willis Day.
Soon after Will Bailey’s untimely death in 1918, Robert and Ben, together withPhyllis Day, invested in the sawmill industry. Since Keystone did not have a nearby railroad for transportation purposes, they were forced to move their business to Junkins. Regrettably, Ben Bailey made a trip to Edmonton in an effort to sell some of their wood and, instead, ended up losing all of the profits in a spirited poker game. When Ben did not return to Junkins, Robert was unable to pay the mill workers. The disgruntled employees started vandalizing the equipment and killing nearby livestock. Forced to close the sawmill, Robert fled to Edmonton.
While living in Kansas, Ben Bailey had a serious girlfriend named Mabel. Having established his homestead in Keystone, Ben requested that Mabel move to Canada to join him. She obliged, and the two were married in 1911.
While in Keystone, Robert Bailey met Mary Chandler, daughter of one of Keystone’s most prominent midwives, Phyllis Day. Robert and Mary married and had three sons: Lesley, Harvey, and Eddy. Harvey became a famous boxer. Known as “Flash” Bailey, he won the Western Canadian Featherweight Championship in 1935.
Times were difficult for members of the Bailey family during the Great Depression. They struggled to make ends meet and lived on relief payments from the government while the men raked asphalt and mined coal. Eventually, several members of the Bailey family relocated to Calgary, where many of their descendants now live.