Ulwaluko or Traditional Male Circumcision is an old African practice that has survived years of criticism and attenuation of Western civilization through religion and education. With the growing Western influence on the continent, there is mounting questioning of the virtues of ulwaluko in some circles even amongst Africans themselves. Proponents of ulwaluko see the ritual as a potent tool for leadership development amongst young men. By adopting a qualitative research design, the authors collected data by interviewing young men who recently performed the ritual. Adopting a phenomenological approach helped the author understand the lived experiences of the target group. The researcher found that over time, there have been influences that sought to weaken and derail the intended objectives of ulwaluko. The researcher also found that leadership development has always been and continues to be integral to the ritual. The recommendations from the study are that the custodians of African cultural beliefs, customs, and values should reclaim their scope of influence and dominance on cultural practices. Greater awareness also needs to be created of the virtues of ulwaluko particularly amongst the younger generations. The author concludes that ulwaluko still plays a pivotal and prominent role in leadership development amongst young African males and that its benefits cannot be undermined.