The Bentley Was a Prison.

Hugo Maynard grew up in the worst part of St. Thomas in the US Virgin Islands. He was selling drugs at five. He watched his brother get murdered. Then his sister came and got him, took him to California, and gave him a different life.

He spent the next two decades winning an Olympic medal, building a pharmaceutical company, and acquiring everything the world told him to want. Then he sat in his Bentley and felt nothing.

His reconnection to his West Indian roots did not start on a plane back to the islands. It started with brutal honesty with himself. From that truth, his family's story, a father who jumped on a piece of plywood with $17 to sail to a better island, a mother who was homeless and pregnant, a bloodline that ran all the way back to a prime minister, started to make sense.

This episode is about what happens when the life the world sold you stops working. And what it takes to go back to where you actually came from.