In 1848, the burly six-foot tall youth settled in Portsmouth, Ohio, where he became a journalist—first at the "Portsmouth Dispatch" and later editor of the "Portsmouth Democrat." The following year, 1849, he was admitted to the Ohio Bar but did not practice. Instead, by 1851, abolitionist activities caused Ashley and his wife to flee north to Toledo, Ohio to avoid prosecution under the Fugitive Slave Act of 1850. There, Ashley opened a drug store (which was soon burned down) and also became involved in the new Republican Party, campaigning for its presidential candidate John C. Fremont and congressman Richard Mott.