Combating piracy is an age-old mission for international navies, as piracy has troubled ocean-going vessels for centuries. Somali piracy, like all piracy uprisings in the past, is a land-based problem stemming from a dysfunctional government that cannot enforce the laws of the land. This lack of law enforcement is what provides pirates a safe harbor to operate, which allows the problem to trickle into international waters and become a maritime problem. However, in the case of Somali piracy, leaders from the U.S. State Department and the U.S. Navy have said there is too much water in the Indian Ocean for the coalition navies to effectively patrol. This thesis first demonstrates how the MMOWGLI platform can be used for crowd-sourced brainstorming of strategic options for counter-piracy, yielding valuable action plans that can be modeled, simulated, and analyzed to make strategic decisions. Three highly rated Action Plans from the 2012 Piracy MMOWGLI game were then modeled and simulated using Discrete Event Simulation (DES). Simulation analysis suggests that the amount of ocean is not a factor if coalition navies aggressively patrol the Somali coast, either directly off shore from active pirate camps or by the use of a naval quarantine. Strategy development for counter-piracy, like any other wicked strategic problem, is usually conducted by senior naval leaders in the upper echelons of specific commands. The MMOWGLI game-play from Piracy MMOWGLI and other MMOWGLI games suggests the U.S. Navy needs to consider utilizing a broader range of officers, enlisted personnel and civilians for brainstorming strategic options. There are an unprecedented number of enlisted sailors with degrees and junior officers educated in joint professional military education. It is time the military taps into this knowledge base for help in planning and implementing strategy.