Historical:
Stede Bonnet was born in 1688 to Edward and Sarah Bonnet. They owned an extensive sugar plantation in Bridgetown which Stede inherited in 1964. In 1709, he married a woman named Mary Allamby. Together they had four children: Allamby, Edward, Stede, and Mary. His son Allamby died in 1715 which is theorized to have had a profound effect on Stede.
At one time, Bonnet held the rank of major in the Barbados militia. During his service, The War of Spanish Succession was taking place. Whether he took part in that or any combat is unclear. For unknown reasons and despite knowing nothing about seamanship, Bonnet turned to piracy. In the spring of 1717, he abandoned his family in the middle of the night. It is also unclear why he made this decision as there is no recorded major event in his life at that time. The most common theory is that he left because married life displeased him.
Most pirates stole their ships but Stede purchased one legally and enlisted a crew of 70 men. He named his vessel The Revenge, though it is unknown what he was seeking revenge about. He had a good education and lived a privileged life especially as compared to other pirates. At the time, most were impoverished and unable to find means of legal work. Speculation suggests that he chose a name that he thought would sound fearsome.
Instead of giving his crew cuts of the goods they stole, as was tradition, he gave his crew set wages. This system prevented mutiny as the crew was dependent on him. He was known for burning ships in his early career which gave him a brutal reputation despite the opinion of his crew who found him incompetent.
Many took notice of his peculiar style of running his ship and his refined ways. He often wore powdered wigs and fancy clothes which contrasted usual pirate attire. Due to this and his wealthy upbringing, Stede Bonnet was called 'the gentleman pirate'.
In a fight with a Spanish man of war, Bonnet was badly wounded. After attaining his injury, he partnered with Blackbeard (yes the most famous pirate ever!) who ran both ships as Stede healed. Once recovered, he again took command of his ship and separated from Blackbeard.
In 1718, Bonnet was captured and knew that he would be executed. He begged for his life in a passionate letter to Governor Johnson. The governor commented on his 'disintegrated mind' which garnered him sympathy among civilians, especially the female population.
He escaped prison in October most likely by bribing a local merchant. He reestablished himself under the name Captain Thomas and changed the name his ship to Royal James in hopes of avoiding the attention The Revenge attracted.
He was located by the British Navy and fought his last battle known as the Battle of Cape Fear River. There the British navy cornered him at the mouth of a shallow river. He chose to fight as opposed to sailing through the river in the dark. Bonnet said that he would blow up his own ship before he would surrender but his crew overruled him. After a vicious trial in which Stede begged for his life on the grounds of his past wealth and status, Stede Bonnet hung on December 10, 1718.

My take:
Stede Bonnet represented English power coming into the new world. He was a child of the established British rule and benefited from the system pirates fed on.
So the question remains: why did he become a pirate? Is it true married life forced him to abandon his three surviving children? It seems a poor excuse to leave a wife alone to support herself and run a plantation on her own. Another theory states that after his son Allamby died, he was no longer able to function in proper society. A record shows that he had taken out a loan before he left Bridgetown, perhaps showing he had fallen into debt.
For whatever reason, he fled his old life in Barbados and there must have been something he was running from. At the time, pirates were often looked upon as a robin hood figures. Bonnet joined the ranks of romanticized pirates such as Anne Bonny and Blackbeard. If he was seeking fame, he succeeded although what he was looking for is unclear.
During both trials Bonnet revealed a desperate struggle for self-preservation. If his goal was a long life and endless riches he failed. Then again, wasn't that what his life on Barbados promised? Perhaps Bonnet wanted the uncertainty of piracy to escape his mundane life of privilege. In the next chapter, we will meet Stede Bonnet after escaping his first trial. Bonnet will struggle with his motivation and the morality of his actions as he is met with a memory of his past. With any luck we will answer: what drives a rich man to crime?