Students who are adept in modeling with mathematics have the capability to use mathematics in situations that arise in everyday life. The German Tank problem described in this article created the expectation that student reasoning was rooted in logical deductions (NCTM 2000). By engaging in this problem, students grappled with challenging mathematics in which they assumed the role of analysts creating mathematical models to understand historical events that influenced strategic planning during World War II. This interdisciplinary task provided students with the opportunity to see data as more than just numbers, but numbers with meaning that can have a substantial impact on the decisions affecting and influencing real-world outcomes.