Games involving strategy can be classified into two buckets: winner’s games or loser’s games. The difference is that a "winner’s game" victor utilizes superior maneuvers to overwhelm opponents, whereas a "loser’s game" victor avoids fatal errors and self-sabotage. Investing has been labeled the latter type, discussed further in a recent article titled "Avoiding the Zeros." Nick Maggiulli references historical events and a simple portfolio simulation to illustrate the impact of catastrophic drawdowns upon long-term returns. Despite the expected outcome of one portfolio exceeding another, over a prolonged time horizon, long-term returns do not produce the same result, thereby illustrating the impact of path dependency. Maggiulli references real-life examples as further support of this concept. Long Term Capital Management imploded in the late 90’s, despite boasting a team of Nobel Prize winners, due to excessive risks and a tail event collapsing both the fund and endangering global markets. Even by playing the odds, when involved in a loser’s game, avoidance of massive implosions is key to attaining respectable long-term returns and relative outperformance.