At 65, Simon Cowell Leaves Behind a Fortune That Makes Fans Cry From a troubled childhood to public scandals and physical setbacks, Simon’s journey is a testament to relentless ambition and personal growth. The man who built his kingdom on broken dreams and golden voices is now stepping off the stage forever. At 65, Simon Cowell leaves behind not just a staggering fortune but also a legacy that has fans weeping like contestants after a crushing rejection. His empire, worth hundreds of millions, now feels like a haunting encore—glittering riches shadowed by the silence of his departure.