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Major League Soccer has long been criticized for its “Byzantine” roster rules and regulations, rivaled only by the Internal Revenue Code in its complexity. Is this criticism fair? By delving into complexity theory and the unique nature of the league, this Article argues that the traditional complaints may not apply in the context of the league’s roster rules. Effectively, critics are applying the standard used to evaluate the legal complexity found in rules such as statutes and regulations when the standard used to evaluate contractual complexity is more appropriate. Major League Soccer’s system of roster rules is the product of a contractual and organizational arrangement among the investor-operators. Its rules are complex in order to keep the investors aligned toward a common goal, while remaining flexible enough to pursue new opportunities and to react to changing circumstances. Although this complexity frustrates fans and other outside observers, it may be essential to ensuring the continued stability and future growth of the league.