Complex sentence: He had waited until he had earned enough of the guards' trust that he could obtain the privilege of not being chained, he then paid off a local farmer with money he had received from his brother in Newark and headed to New Jersey.
Split into simpler sentences: He had waited until he had earned enough of the guards' trust that he could obtain the privilege of not being chained. He then paid off a local farmer with money he had received from his brother in Newark, and headed to New Jersey.