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The idea of creating "winning" characters in Dungeons and Dragons is, to some degree, to miss the point of the game. Dungeons and Dragons is a cooperative game. The players of the game work together to overcome specific challenges designed by the Dungeon Master. More than that, though, the players interact one with another and each with the Dungeon Master in a collaborative storytelling effort. To suggest that there can be "winning" characters in Dungeons and Dragons is, really, a puzzling concept.

Having said that, players do enjoy playing characters that are able to win in combat. In that sense, creating winning characters in Dungeons and Dragons certainly could really just refer to the process of character optimization. Optimization is the process whereby a player selects race, class, feats, skills, equipment and other abilities in order to maximize the effectiveness of their character. Typically, optimization happens so that players can have characters that win in combat.

There are different schools of thought about creating optimized or "winning" characters in Dungeons and Dragons. One side of this argument suggests that character optimization is a useful and normal part of the game. They argue that the feat and skill combinations that exist in the rules exist together for a reason, and that choosing elements that complement one another isn't just a good idea, it is what the designers of Dungeons and Dragons had in mind when they created the game.

On the other hand, there are those that believe creating optimized or "winning" characters in Dungeons and dragons takes too much away from the role-playing aspect of the game. They argue, for example, that it doesn't make any sense for a character to have one level of rogue, one level of ranger, three levels of fighter, and then two more levels of rogue. They would rather see characters develop more organically, and in line with a story.

The best approach, probably, is to create a balance between organic development and optimization. In reality, these are the most "winning" characters in Dungeons and Dragons, if for no other reason than the fact that they are more interesting and fun to play with, and to play alongside.

Learn more about this author, John W. Paulus.
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