A hot-shot is a person of great success. Those on the other side do not have this success and are therefore at a disadvantage. It is the people who have succeeded in life that continue to succeed and eventually win in life. Although success cannot be exactly measured, a person cannot succeed without having prior success. For example, a person cannot be an aspiring artist, singer, or author without having succeeded in that field before. Because of this lack of success, those on the other side cannot play the game of life.
Hot-shots do not only have success however. By putting himself on the other side, Holden alienates himself from the rest of society and may therefore mean that those on the other side are as well alienated from society. Those on the other side cannot play the game of life because it is the people who have fame and recognition who are successful. They have support, experience with people, and connections. Because the people alienated from society lack these advantages, they cannot play the game of life.
Furthermore, there is another factor which whether a person can play the game of life. People usually associate success with money, or fortune. When a person has great fortune, they have great success. This fortune however is what makes the hot-shots successful in the first place. Fortune is not only defined as money though. It includes any type of resource or pure serendipity. All fortune however makes people successful, either by allowing them an education or opening up opportunities that would not be available without it.
People on the other side do not have fortune and therefore do not have the means to play the game of life. So who can really play the game of life? Hot-shots are the one who can play the game. Their access to success, fame, and fortune allows them to play the game of life and win in it. Those on the other side do not have access to these advantages and can therefore not play the game of life and not win in life. It is not until a person transitions into the hot-shot side can they truly be successful in life.