Ku qor sii wadida cutubkan - 1895kii, Older wuxuu noqday maamulaha tifaftiraha "San Francisco Bulletin" (oo markii dambe lagu daray "San Francisco Call" 1929). Wuxuu caan ku noqday markii uu la wareegay mashiinkii Boss Abe Ruef ee San Francisco, intii uu ahaa duqa magaalada Eugene Schmitz. Tani waxay keentay maxkamadeynta musuqmaasuqa inta lagu guda jiray dib u dhiska San Francisco ka dib dhulgariirkii 1906
iyo Naar. Bishii Sebtember 27, 1907, Older ayaa la afduubtay waxaana ku hanjabay dil by baaritaanka gaarka loo leeyahay Luther Brown, ayaa la sheegay in ay u shaqeynayeen grafters.