In this paper the issues of how to improve student engagement and as a result, student success in schools will be scrutinized. The ideas of Rousseau, Pestalozzi and Montessori will be addressed along with modern educators teaching in predominantly black communities. From these educational professionals, their ideas, and studies done more recently, the author will suggest another factor that can negatively affect student engagement: an inability for students to see themselves having bright futures. Schools are a place where improvements can always be made. In the beginning, the school system in the United States was focused on availability for students. The Old Deluder Satan Act of 1647 and the Land Ordinance of 1785 required settled lands to have space set aside for schools and schoolmasters to teach in these schools. As years continued, the country saw further development of educational infrastructure with the first installation of the Department of Education in 1867. This signified the first step towards monitoring our nation's schools and the country's educational standing compared to other nations.