Gillette is not an artistic man in the traditional sense; he sees the world in too practical a manner to get lost in paintings or fashion. Theater was a luxury he did not afford himself, when he could instead spend his time advancing his knowledge of the articles of war, the histories of battles recent and far gone. He had a passion for reaching back in time and seeing how others managed their odds, and fashioning scenarios and resolutions.

Soon, he found himself writing down operations, calculations and various other elements in order to better exercise his understanding of command. He eventually engaged his mother in the game, and slowly it evolved to something more. Now, when he gets letters from her, he gets several tests to work on, scenarios and battle plans, and he writes like a man running out of time to work out the best solutions, the clearest paths to victory, never knowing that more often than not his plans are not nearly as hypothetical as he believes them to be.