A gifted naval tactician and born commander, Gandry was a rising star in the Monquistan Navy when a matter of honor and a duel led him to renounce his commission and defect to Polaris, where he quickly earned the rank of Captain, acquired a thick Polarian accent, and served with distinction in Napoleguin's Navy. At the peak of the Polarian Wars, a dispute with a fellow officer led him to leave the Polarian Navy and jump ship to serve in the Marleybonian Navy. Before long, Gandry led a mutiny and became a Pirate.
After a brief stint as an independent Privateer, he joined forces with Boochbeard, and has served as his first officer longer than he lasted in any of his three navies. Some suspect that Gandry is the real brains behind Boochbeard's operation, and that the monkey is content to hide behind the buffoon and use him as a figurehead to hide his true scheme.