The extent to which organizational, social, cultural, and leadership contexts within schools support or impede the complexity of emergent leadership as it relates to professional learning communities was investigated in this study. Through in-depth interviews exploring ways in which teacher leadership manifests itself, the ability of teachers to understand their own leadership capacity, and how their emergent leadership influences others, data from this study reshape the notion that schools do not need to reform, but need to transform from traditional schools of teaching into contemporary schools of learning, providing the type of professional knowledge needed to foster 21st century skills for students. Data were collected through one-on-one semi-structured interviews conducted With fourteen teachers from four schools designated as the highest and lowest Title I and Non-Title I schools in a large urban district based on state wide achievement scores. These interview data were analyzed to develop five thematic constructs with sixteen themes. Thematic constructs were also developed to address the four context factors that may support or impede emergent teacher leadership. The findings suggested that teacher leadership has the ability to develop through the process of collaboration which is socially constructed in the context of professional learning communities. Findings further reveal that deep considerations for the ramifications of working within such a complex system as a learning community be made. These considerations include understanding that teacher leadership leads to a shift in decision making from a hierarchical to democratic model, that collaboration builds organizational intelligence, that struggling students are motivators for reflective professional discourse, and that influential peers set the model for this type of intuitive teacher leadership. Implications for further practice and directions for future research are also discussed