There are companies out there that profess to be able to take a portfolio and run it through some statistical analysis that will give you that type of simulation.
Instead of rehashing what has already happened in a simulation-type game, "Assassin's Creed III" aims for the gray areas of history and focuses on events that may not have a clear-cut explanation.
Strategy board games back in the 1970s and '80s, like "Blitzkrieg" and "War in Europe, " were simulation-type games requiring players to spend a lot of time rolling dice to resolve combat or find out different game stats -- weather conditions, civil unrest, troop rally points.