The creator of the winning entry in the MongoDB World Weekly Challenge created a digital Rube Goldberg machine that used Stitch and multiple APIs to generate a GIF based on the user's astrological sign. The process starts with Facebook Messenger, where the user selects their sign, triggering a series of events that ripple through multiple triggers and functions, ultimately leading to the generation of a customized GIF using the Giphy API. The winning entry was notable for its intricate code and creative use of APIs and services.