Once gaining the captaincy Rackham made a career of plundering small vessels close to shore. He and his crew captured the Kingston, a small Jamaican vessel, and made it their flagship. They made several conquests in the West Indies, taking a couple of large ships off of Bermuda.
In 1719, Rackham sailed into Nassau in the Bahamas to take advantage of a general amnesty for pirates, in hopes of obtaining a royal pardon and commission from Governor Woodes Rogers. Rogers had been sent to the Bahamas to address the problem of pirates in the Caribbean who had started to attack and steal from British ships.
The British government later sent him to Jamaica as governor to give out pardons, in the hope that most would either give up their life of piracy or join the British against the Spanish.
Rackham had plenty of treasure and a reputation as a good pirate, but he was only able to receive a pardon. Rogers would have given him a commission if he were able to take Spanish ships, but he had little faith that Rackham could defeat larger Spanish vessels.