makes you wonder if it is the same person... seems he was trying to find a job he really liked
1900 census farmer
1910 census merchant
1920 census cigar stand manager
1930 census painter
I did see marriage to alice: http://search.ancestry.com/cgi-bin/sse.dll?viewrecord=1&r=an&db=FS1MontanaCoMarriages&indiv=try&h=334398 it shows he was previously married and divorced (possibly a 3rd marriage to millie borden http://search.ancestry.com/cgi-bin/sse.dll?viewrecord=1&r=an&db=FS1MontanaCoMarriages&indiv=try&h=901490)
also saw an obit, http://mv.ancestry.com/viewer/7727e93b-b83c-4d7e-8bb1-e6a311d49b76/20088092/895094718 that says he was city marshall, county deputy, then a police officer from 1910 to 1913, a few months in 1925 then deputy sheriff and later a guard at state penitentiary