The winning entry titled "Most competitive" leverages complex Ruby tricks to obfuscate a program that evaluates itself. It uses techniques like dynamically generating code strings, manipulating character encodings, and exploiting edge cases in Ruby's parsing and evaluation rules. The goal is to demonstrate both the robustness of Ruby interpreters in running such esoteric code, as well as uncover subtle aspects of Ruby's specification and implementation. The judges awarded it high honors for achieving the contest's goals of producing transcendental, imbroglio code.