[104] In March 1859, Grant freed William by a manumission deed, potentially worth at least $1,000, when Grant needed the money.[105][k] Grant moved to St. Louis, taking on a partnership with Julia's cousin Harry Boggs working in the real estate business as a bill collector, again without success and with Julia's prompting ended the partnership.[107] In August, Grant applied for a position as county engineer, believing his education qualified him for the job. He had thirty-five notable recommendations, but the position was given on the basis of political affiliation and Grant was passed over by the Free Soil and Republican county commissioners because he was believed to share his father-in-law's Democratic sentiments.[108] In the 1856 presidential election, Grant cast his first presidential vote for Democrat James Buchanan, later saying he was really voting against Republican John C. Frémont over concern that his anti-slavery position would lead to southern secession and war and because he considered Frémont to be a shameless self-promoter.[109]
In April 1860, Grant and his family moved north to Galena, accepting a position in his father's leather goods business run by his younger brothers Simpson and Orvil.