While the juvenile correctional juvenile correctional system in South Africa faces a plethora of challenges, there is a potential to reshape the education system through a collaboration of philanthropic interventions and transformative leadership. Improved educational environment for juvenile offenders enhances rehabilitation and reduces recidivism rates. However, despite the growing acknowledgement of the importance of rehabilitation through education, research on how targeted philanthropic interventions could bridge the systemic challenges is limited. The main objective of this Grounded Theory study was to focus on the potential of philanthropic support to empower transformative leadership to bridge the resource challenges within South African juvenile correctional facilities. Grounded in relevant literature, this study employed a grounded theory methodology to generate data through observations and open-ended interviews and analysed to develop a framework for best leadership and management practices. First, the participants advocated for an inclusive and participatory environment where all stakeholders actively engage in shaping the educational and rehabilitative programmes through collaborative empowerment. Secondly, it is essential to create supportive environments that enable effective education and rehabilitation. Lastly, strategic partnerships emerged as central to the success of philanthropic interventions. The findings suggest that educational leaders should engage transformative practices to contribute to reduced recidivism and successful reintegration.

Keywords: Juvenile Correctional Education, Transformative Leadership, Correctional Philanthropy, Educational Management, Social Justice, Recidivism Reduction.