So most of the Caribbean pirate captains have already been mentioned, so I’ll focus on my speciality: piracy in the Indian Ocean and the Indonesian Archipelago.

Your main question is ‘When is a pirate considered to have been successful’, and I’d like to take that to show that success was (and is) fleeting. Take one of the most successful pirates in Western history: Henry Every, the King of Pirates. He managed to lead a small alliance of various pirate vessels in an attack on the convoy of Mughal vessels headed for the annual pilgrimage in Mecca. The ships were loaded with treasures and envoys from the Mughal emperor.(1) In one swift (but bloody and horrifying) attack, Every became the richest pirate in history. However, Every quickly vanished and retired somewhere. According to some he died poor, losing his money to various failed ventures. He perfectly fits the image people have when they hear the word ‘pirate’: an European man who sails the seas and captures ships, only to mysteriously vanish with a huge treasure.

Thing is, the vast majority of pirates throughout history (and prehistory) do not fit this picture at all. The romanticised pirate, swash-buckling and drinking his way through life, is based on a small group in a very small timeframe. If you’d look at the pirates that attacked Dutch and British Indian Company ships, raided shores, and attacked riverboats, you’d be surprised to find them quite different than the pirates you know. Contrary to the famous pirates like Blackbeard and Henry Every, pirates in the Eastern hemisphere generally weren’t ‘full-time’ pirates, or didn’t consider themselves to be pirates at all.

Imagine the Indonesian Archipelago: busy trading-routes were thousands of ships (European Eastindiamen, Chinese Junks, canoes, coastal barges, fishing boats) travelled through narrow waterways, flanked by lush islands hiding innumerable inlets and natural harbours. With so many prey and just as many hiding places, piracy was a matter-of-fact in that area.

I quote a 14th Century Chinese historian:

“The inhabitants are addicted to piracy [..] when junks sail to the Western [Indian] Ocean the local barbarians allow them to pass unmolested but when on their return the junks reach Chi-li-men [the Karimun islands] the sailors prepare their armour and padded screens as a protection against arrows for, of a certainty, some two or three hundred pirate praus will put out to attack them for several days. Sometimes [the junks] are fortunate enough to escape with a favourable wind; otherwise the crews are butchered and the merchandise made off with in quick time.”(3)

But there is barely any mention of ‘real’ pirates. That is to say, larger-than-life personalities that became a terror of the seas. No, piracy was committed by everyday people who saw opportunities. People, especially transient sea-faring people, worked day-jobs: one day they worked the fields, the other day they helped load ships, after a few days they fished, and some days they attacked other ships. Often, these jobs leaked over into each other: trade vessels that encountered a weaker/smaller ship at sea that made for an easy target might suddenly decide to attack said ship and steal its cargo. If the ship was deemed too strong, they’d continue their original ‘role’ as traders.

Violence was seen as an important element of statecraft: by committing piracy or by protecting against piracy, the small states around the Archipelago would claim their territory and their influence.(4) And not every act of piracy was seen as piracy by the perpetrators! A Mughal ship attacked a British ship three years after Every’s attack and claimed it was retaliation for that attack. It shouldn’t come as a surprise that the British didn’t agree with him. The ‘Angrean Pirates’ that attacked a Dutch ship sailing near the Westcoast of India weren’t pirates at all but the naval force of the Marathan Empire: they demanded to see permission-letters, but the Dutch did not acknowledge their sovereignty over the area and refused.(5) The following attack was recorded as a violent pirate attack, but if the roles were reversed (if an Marathan ship would sail through Dutch territory and refuse to show papers) the Dutch would attack it and feel justified in doing so.

History is written by the victor, and these examples show that the concept of piracy (violent attacks on sea to capture cargo or humans) differed quite heavily from one part of the world to the other. That doesn’t mean there weren’t ‘real’ pirates active in those areas. One could look at Zheng Zhilong, a Wokou/Chinese pirate that assembled a giant fleet of hundreds of Junks and commanded thousands of pirates. He became so powerful that the (waning) Ming government offered him a position of admiral, a cushy job he’d gladly accepted. Or what to think of Ching Shih, considered to be the greatest pirate that ever lived (there’s a good qualifier for your question). She was said to have commanded between 20.000 to 40.000 pirates in the early 19th century.(6)

But a more modest (and perhaps better) example is that of Cottim Collan Coenja Amadoe. We learn of Coenja through the confessions of one of the crew of his ship to the court of the Dutch Eastindian Company.(7) The court case recorded the following story:

On May 7th, 1747 the ship Francisco Alfonzo (captained by Zoqusinaij) travelled along the West Indian coast towards Goa, carrying 25 packs of tobacco (and a myriad of other things, all neatly recorded in the court case). Suddenly, they were beset by a small boat and pirates entered the ship. One of the assailants swung his sword at the first mate, wounding him, after which the crew surrendered. Their entire cargo was stolen and the pirates sailed off. The crew immediately set sail towards the nearest harbour to report the attack, and as they moored they saw… the pirate ship, unloading THEIR cargo. The captain quickly went to the nearest Dutch garrison and told them what had transpired. The entire pirate crew was arrested and interrogated. One of those questioned was Amadoe (not to be mistaken with the captain), a young boy. In his statement, he identified Cottim Collan Coenja Amadoe (let’s call him Coenja) as the pirate captain and stated that he “has been living a very rich and public life, thanks to his piracy.” and that Coenja had done so “Before I [Amadoe] was born”. Seeing that Amadoe stated he was around 20 years old, it would seem that Coenja had a long and successful life as a pirate!
An interesting tidbit about Amadoe’s confession confirms that piracy wasn’t a ‘full-time job’ for most. Amadoe said he was a Koelie (a dayworker) and that while yes, he was working on board of Coenja’s pirate vessel he himself had not participated in the attack and therefore wasn’t a pirate. He was just a dayworker. He also said he wasn’t aware that Coenja was planning to attack another ship (even though he apparently was a well-known pirate), but that they were supposed to trade. Both Coenja and Amadoe were handed over to the local king (as per agreement between the Dutch and the king), but chances are they weren’t punished.

So when is a pirate successful? One could argue that the most successful pirates were those that we still remember: Blackbeard reign was short but everyone knows his name, Every might’ve died poor and alone but he was given the title King of Kings. Or maybe it’s the Indian pirate Amadoe who managed to live a very comfortable and public life from his piracy? Or were the biggest pirates the Dutch and British Eastindian Companies who enslaved, murdered, and exploited millions of people throughout the centuries? You decide!

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(1) P.J. Stern, ‘"A Politie of Civill & Military Power". Political Thought and the Late Seventeenth-Century Foundations of the East India Company-State’, Journal of British Studies, Vol. 47, No. 2 (2008) 253.

(2) A. Reid, ‘Violence at Sea: Unpacking “Piracy” in the Claims of States over Asian Seas’, in: R. J. Anthony (ed.), Pirates, Pervasive Smugglers: Violence and Clandestine Trade in the Greater China Seas (Hong Kong 2010) 15- 26, 17.

(3) Eklöf, Pirates in paradise, 6.

(4) A. Reid, ‘Violence at Sea: Unpacking “Piracy” in the Claims of States over Asian Seas’, in: R. J. Anthony (ed.), Pirates, Pervasive Smugglers: Violence and Clandestine Trade in the Greater China Seas (Hong Kong 2010) 15- 26, 21.

(5) H.C.M. van de Wetering, ‘De VOC en de kapers van Angria. Een expeditie naar de westkust van India in 1739’, Tijdschrift voor zeegeschiedenis, Vol. 10, Afl. 2 (1991) 119.

(6) Dian H. Murray 1987, p.64.:Murray, Dian H. (1987). Pirates of the South China Coast, 1790-1810.

(7) Dutch National Archive. Archivenumber 1.11.06 Inventorynumber 440, scans 43 – 79.

I’m not sure if I really understand the question here. What is it you mean by great? Just successful? There were a lot of successful pirates who were often successful for different reasons and in very different circumstances. It also depends what you mean by successful. People like Bartholew Roberts and Blackbeard captured a lot of ships but they were both killed within a few years and most of their crews were hung.

A book I would recommend about the pirate Edward Thache is Quest for Blackbeard: The true story of Edward Thache and his world by the author Baylus C. Brooks who has recently done a lot of original archival research to discover a lot about Thache’s early origins and family as well as his career. If you’re interested in learning more about Blackbeard, that’s definitely the book to read.