Historians, authors, and students of military history intuitively gravitate to the glorious battles and tactics of the great captains. All revel in the great captain's ability to use ingenious military tactics and maneuvers to win decisive battles. However, history continually reveals a hard lesson; decisive battles do not necessarily result in strategic success. Great captains with a strategic vision or a grasp of the grand strategy are able to link tactical victory to strategic success. Additionally, great captains who avoid a direct attack and employ an indirect approach, utilizing all available means, are able to achieve their grand strategy and a lasting state of peace. Analysis of theses concepts starts by defining grand strategy and the indirect approach, discussing the importance of looking beyond battles and linking military strategy to grand strategy. Next, the analysis of two struggles for national survival highlights four great captains. The Second Punic War, with Hannibal vs. Scipio, and the American Civil War, with Grant vs. Lee, provides definitive examples of both success and failure of great captains to link military strategy to grand strategy. Hannibal and Lee are widely studied by historians for their tactical genius. However, their limited grasp of grand strategy and insistence on direct attack to achieve a decisive victory, lead to their defeat by lesser-known great captains. Scipio and Grant understood grand strategy and used an indirect approach to attack the enemy's weakness, linking military victories to strategic success. Finally, although separated by 2000 years, the study of these great captains and their strategies provide timeless lessons for today's warrior leaders.