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Most professional athletes are broke financially within a short few years after they stop playing. It is easy for outsiders to place the blame squarely on the athlete himself. This rush to judgment, however, is not entirely accurate. Black student-athletes who have the talent and ability to play professional sports are hyper-focused on getting to the next level, and the system around them is built to accommodate that focus. A lack of educational, financial, and legal structures creates a dynamic that sets the athlete up for failure. This chapter will focus on the legal and financial realities that Black males face when transitioning into and out of professional sports. In order to shift the current paradigm, this chapter will also provide solutions for both the athlete and the coaches, friends, family members, and agents who surround the athlete, in order to empower the athlete to positively impact himself, his family, and his community.