This essay is an autobiographical examination of who and where I am on the plane of racial and ethnic relations. As such, it is written in a spirit of self exploration and scrutiny, measuring my beliefs and feelings against popular theories of race relations in the United States. I focus on specific historical incidents that I believe influenced my place in the racial world in which I live. In the first portion of the article I evaluate the influence demographics and family have had in my life from childhood through adulthood. I examine the beliefs of my parents and peers and how they might have influenced me growing up in middle-class suburbia. Despite the influence adults have on the development of personality, beliefs and attitudes are shaped further through adult interaction. Therefore, in the second portion of this article I describe the influence military service and post military employment in law enforcement has had on my understanding of race, racism, and discrimination. In conclusion, I argue, the idea that somehow the many racial groups and cultures in the United States will eventually merge into one coherent society seems like an improbable concept. There have been obstacles placed in the path of fairness and equality by institutions and persons who did not have the benefit of the science or reason of today. The concept of a level playing field is not one that I embrace, as I once did. The game started centuries ago and unfortunately there were no referees to make sure the rules of engagement were clear to every player. As such, the game has progressed in favor of the game’s creators. The only way to level the playing field is to clearly redefine the rules of the game or to play a different game altogether. As in sports, it is a difficult task to convince the winner that he is winning unfairly if the reward for victory is wealth and power beyond imagination.