Embodiments of the present invention provide a trailed multiple-viewing-angle item inspection system and method of operating the same. The inspection system includes: a trailer vehicle, a radiation inspection device, a power supply device and a power grid connection device. The trailer vehicle is mounted with a power supply chamber within which a power supply device and a power grid connection device are mounted and an inspection chamber within which a radiation inspection device is mounted. The radiation inspection device includes: ray radiation source configured to emit X-rays from various positions, detectors, a body frame, a transfer device, a data and image process system and a display and operation device. The trailed multiple-viewing-angle item inspection system of the present invention can obtain a transmission image containing depth information of an item by its one pass through the device, and achieve a high-speed inspection, a good image quality and a high inspection efficiency of hazardous articles, and its flexibility and movability can meet requirements in various working conditions.