This article describes a mathematical model that connects mathematics with social studies. Students use mathematics to model independent versus convoyed ship deployments and sinkings to determine if the British should have convoyed their merchant ships during World War I. During the war, the British admiralty opposed sending merchant ships grouped together in convoys for several reasons that proved to be false. This author proposed the problem of whether or not the British should convoy their merchant ships to preservice teachers in a course in mathematical modeling for middle school teachers. While working on this problem, the students analyze and rebut each of the admiralty's arguments against convoying. Not only does this problem tie directly to social studies, it makes connections within mathematics. To solve the problem, students must first develop a clear statement of what they need to do (i.e., they must clearly identify the problem). They must model and solve a contextual problem using multiple representations. They need to analyze the situation using algebraic symbols when stating the identified recursive relations algebraically. They must use visualization and geometric modeling along with probability. Finally, they must communicate their solutions and recommendations in writing. Thus, not only does this problem address the Content Standards of algebra, geometry, and probability, it also attends to the five Process Standards of problem solving, reasoning and proof, communication, connections, and representation (National Council of Teachers of Mathematics 2000). (Contains 7 figures.)