This chapter details the selection of Octave Chanute to design and build a lasting bridge across the unbridged Missouri River at Kansas City. The offer to bridge the Missouri, the most difficult of all navigable streams, was a compliment for Chanute, but also a formidable challenge to his ambition as a civil engineer. The completion of the bridge called for the construction of about four hundred miles of connecting roads, bringing urbanization to the Kansas frontier. The thirty-seven-year-old Chanute built this rail system and connected it with eastern railroads, bringing profit to both systems. During the first 230 days of operation, 5,263 locomotives had pulled their load across the bridge, and $5,706 had been collected in tolls from street traffic. The chapter also describes Chanute's appointment as chief engineer of the Missouri River, Fort Scott & Gulf Railroad and his involvement in construction of the Kansas City & Santa Fe Railroad, Galveston Railroad, and Atchison & Nebraska Railroad.