On 1/16/04, Frank O'Connor posted his first weekly update, at the time Halo 2 was still under a vail of secrecy. Frankie had just seen a promotional poster by Lorraine McLees and wanted to include it his weekly update, however it was not possible at the time. So instead Frankie created a horrible artist's impression of it. Instead of Master Chief holding a gun, Frankie drew it with a lightsaber. Saying it was easier to draw a lightsaber instead of a gun. It did not look quite right so Frankie drew in some eyes and mouth and labeled it "Mister Chief".
Frankie got such a response from fans that he decided to include another Mister Chief image in his weekly updates from then on. Mister Chief has been made in many different styles, including immitation Carravaggio and Japanese manga. Most ideas come from fan requests.
Mr. Chief has been replaced in a couple weekly updates by Mrs. Chief, Evil Chief, and HotTub Guy. And in one instance, a calendar.