A trailer stabilizing device for stabilizing a parked freight trailer comprising a frame having mounted thereto at least a right side wheel and a left side wheel, the frame also including a hitch, a fifth wheel, and at least one of a repositionable wheel chock and a repositionable hook, the trailer stabilizing device further including a repositioning device in order to reposition at least one of the repositionable wheel chock and the repositionable hook. The present disclosure also includes a method of stabilizing a parked trailer at a loading dock, the method comprising: (a) positioning a wheeled trailer stabilizer underneath a parked freight trailer at a loading dock while landing gear of the parked freight trailer are deployed and a kingpin of the parked trailer is accessible; (b) securing the kingpin of the parked freight trailer to a fifth wheel of the wheeled trailer stabilizer; and, (c) deploying a repositionable hook operatively coupled to the frame of the wheeled trailer stabilizer so the repositionable hook couples to a cleat mounted to the ground, where deployment of the hook is operative to exert a pulling force on the kingpin.