Historical research usually investigates past occurrences. However, it may be worthwhile to look into what did not take place and why. This essay focuses on the alliance between Artemio Ricarte and Jose P. Laurel that did not happen under the Japanese Occupation of the Philippines (1942-1945). Ricarte was a revolutionary general who fought against Spanish and American colonial forces at the turn of the 20th century. He had been viewed as a staunch anti-American nationalist who sought refuge in Japan and refused to return to the Philippines as long as the U.S. occupied the Philippines. He finally returned home at the end of 1941 along with the invading Japanese forces, whose alleged goal was to “liberate” the Philippines from the U.S. Jose P. Laurel, on the other hand, was one of those high-ranking government officials who had been working hard to prepare the country’s independence under the Commonwealth government in the pre-war period. When the Japanese landed on Philippines soil, he was one of those cabinet members who were ordered to stay behind, while the Commonwealth president, Manuel L. Quezon, and a few other officials left for the U.S. When the Second Republic was inaugurated in 1943 under the Japanese sponsorship, Laurel was elected president. It would be natural to think that Ricarte would have cooperated with Laurel, forging an alliance of sorts, in order to establish the independent Republic. While this had been an ardent lifelong wish for both men, an alliance did not take place and this essay examines why.