Studies reveal that low-SES male students struggle to succeed in classrooms far more frequently than their mainstream classmates --- additionally, they have histories of truancy, transiency, anger issues, behavioral problems, and their middle-class educators claim they possess subpar language, academic, and social skills --- all of which collectively disadvantage them further in schools as compared with their middle-class peers (Aliakbari & Faraji, 2011; Darder, Torres, & Baltodano, 2017; Filmer, 2000; Gabrenya, 2003; Gorski, 2013; Greene, 2008; Hamre & Pianta, 2001; Jensen, 2010; Lemon & Watson, 2011). The lived realities of males with low SES routinely leave them vulnerable in traditional schools, as class structures, unexamined common sense assumptions, and privileged social conditions are found to act as agents that elevate middle and upper class students' successes while reducing educational access and opportunities for low-SES males (Entwisle, Alexander, & Olson, 2007; Filmer, 2000; Giroux, 2009; Hannon, 2003; Jensen, 2010). The pronounced class differential compounds low-SES students' burdens, since middle-class teachers are largely unaware and inexperienced with the life challenges these students routinely navigate; too often they are assigned blame for failures out of their control (McGregor, Mills, Riele, Baroutsis, & Hayes, 2017), deteriorating their membership with schooling, and leaving them to cope with their barriers in isolation (Catalano, Oesterle, Fleming, & Hawkins, 2004; Sorrels, 2015). This qualitative backyard study interrogates the experiences of five low-SES, at-risk males in an alternative school who failed in traditional schools, to gain insights related to the influence of gender, meritocracy, social class, life circumstances, and wealth in schooling from their first-person, narrative, storied perspectives as outsiders in educational spaces. Concluding recommendations focus on strengthening adult/student connectedness, eliminating punitive and de facto disciplinary practices in schools. Preventative measures are outlined for bolstering equity and just practices, school safety, and overall student achievement, while eradicating the steady school-to-prison-pipeline (Brendtro, Long, & Fecser, 2018; Darling-Hammond, 2019; Peterson & Densely, 2019). Training in culturally responsive practices, and positive behavioral intervention supports (PBIS) enhances educator capacity for mitigating student escalations, and multi-leveled school-based mental health therapy is posited as essential for all students in public schools. Curricular enhancements, including mindfulness instruction, support the development of strategies for increased self-regulation. Student-centered practices founded on Maslow's principles are argued as essential for traumatized youth, in conjunction with strong relational trust to optimize learning readiness, and to support the overall increased wellness of the whole child in school spaces (Mcleod, 2018; Poston, 2009; Noddings, 2005).