"Rich" is a subjective term, and there are two answers to this question: yes, in the sense that a number of decent scores or even one large one split favorably would leave a man significant disposable income--certainly enough to make a new life for himself in the New World. However, there was a very real risk involved, and pirates knew full well that any "retirement" was far less likely than an early death.

In the earlier days of piracy in the New World, pirates operated under the command of men wishing to climb the social ladder with significant plunder OR as privateers--essentially pirates given special permission to carry out their deeds against rival powers for the good of their nation and noble benefactor. I'm currently writing my Master's thesis on Sir Francis Drake, who followed this path to a t. He carried out the first English piratical ventures in the New World against Spanish targets. He had no letter of marque branding him a privateer, therefore his actions are considered to be out and out piracy rather than state-sponsored military advances. Even his venture round the world (the very thing most people remember him for today) was actually one based in piracy over exploration. Queen Elizabeth I knew about it, sponsored it, and profited from it, but did NOT grant him a letter of marque in order to cover her tracks and not further strain relations with King Philip II of Spain. He ended up making an obscene amount of wealth from the circumnavigation, and ascended into the English landed nobility thereafter. He went on to earn great fame as a military commander and English patriot through profits originally earned as a pirate. (I have an entire bibliography available that I could post here, but I would have to say Harry Kelsey's "The Queen's Pirate" is a top notch Drake biography for those interested.)

YOUR question, however, pertains to the Golden Age of Piracy--a century after Drake's death in 1596. Pirates from this era (e.g. Calico Jack Rackham, Black Bart, Anne Bonnie, and Blackbeard) were entirely different from men like Drake. Drake and his countrymen were Englishmen first, loyal to Queen and Country though their livelihoods were built around extrajudicial operations.. Edward Teach and his ilk who made their home at Nassau believed themselves free from such...imperial entanglements...

They raided for their own sakes, working to provide for themselves and their crew, but only in their own best interests. They knew that if they could escape intact with decent plunder, they could create a new life for themselves in a European colony. If they ever got the urge for more, they could return to their raiding life at sea under a captain or with their own ship and crew.

These men also knew that such an end was hard won, and not so often awarded as death at sea. The did their best to embrace death--the evidence flew on the breeze above the mainsail. Skulls, bones, demons, murder, even the "Jolly Roger" was an homage to a frank, accepting relationship with death in piracy. By the end of the Golden Age and the establishment of Governor Woodes Rogers in the Bahamas, piracy became far less profitable and far more likely to end at the end of a rope. (For further reading, David Cordingly's "Under the Black Flag" is pretty much the go-to Golden Age of Piracy history, but I also recommend "Pirate Hunter of the Caribbean" also by Cordingly, for a detailed biography of Woodes Rogers and the end of the Golden Age.)

TL;DR: Yes, it was difficult, but it was indeed the end goal for pirates though they knew death to be a far more likely outcome for such a life as theirs. Yo-ho-ho and all that.