Historical Rogues Gallery

Note: This is a revival of a post I originally wrote on ENworld back in 2008. It has been updated, consolidated, and revised for 2021.

One of the biggest challenges for historical fencers, gamers, authors, and anyone drawn to the pre-industrial world, and particularly the medieval world, is the confusion engendered by our schizoid perception of it in the popular culture. On the one hand, we love the idea of swords and knights and castles, on the other we are put off by the Monty Python style clichés of muddy filth, toothless peasants, religious fanaticism, ignorance and disease. In short we like the idea of the ancient world, but we think that the reality is just going to be wildly disappointing. This belief or suspicion persists for generations even though it couldn’t be more wrong.

Why the tropes about the pre-industrial world continue so stubbornly to perpetually shunt us away from history, even at the same time that we are so drawn into it, is beyond the scope of this short essay to fully decipher. All we can say for sure is that it is a real thing and it is a mystery. Popular entertainment franchises Game of Thrones, Lord of the Rings, the Witcher and so on rake in billions of dollars, and somewhat lower budget TV shows like Vikings and The Last Kingdom certainly hold their own, as do video games like World of Warcraft but also more historically oriented fare such as Kingdom Come Deliverance or Mount and Blade. Meanwhile tourist revenue from places with surviving medieval architecture earns perhaps even more.

This tells us that something about the reality of history also has a very strong pull, but at the same time… we can never seem to come to grips with it. For all the magnetic power of life in these remote times and places, we are also repelled, and the repulsion is in part down to a series of Tropes which convince us it is not really worth exploring. That the fantasy one-off is better. Or even the fantasy five-off. This is perhaps why DnD and most other RPGs tend to fall pretty far over into the fantasy camp.

It is a kind of a cultural malady we suffer from, and it is one which goes far beyond the realms of entertainment or martial arts. It’s not something I propose to have a cure for today. I can’t convince people to let go of their preconceptions and Tropes and dive into history. But I can help those who have already navigated their way through these barriers and want to try to explore further. That was my main purpose ten years ago when I started to write the Codex Guide to the Medieval Baltic, and that is my purpose here again. Like an explorer venturing into the lonely mountains of Central Europe, I try to mark the paths, and perhaps slay a few of the dragons along the way.

The Tropes: #1) Nasty Brutish and Short

One argument I have heard many, many times from people who don’t like history or historical fiction, and who prefer high fantasy genres, is that everyone born before air conditioning and iPhones had fleas and dies of the plague anonymously at age 24. As someone myself born before the iPhone, I must admit we did of course have fleas, but some of us somehow survived. When we look even further into history, say before electricity, we quickly get lost and find need of an anchor. We are looking for a hero to identify with, a remarkable person, someone who transcended the mundane, and yet someone that we can still relate to. We certainly don’t want to be anything like our own reality today, but also nothing too foreign.

If you prefer high fantasy the remedy for this is to create a sort of superhero who wears the costumes of what we (very vaguely) think might be like those of ancient times, but who otherwise resembles ideal versions of ourselves. Or ourselves if we were combination fitness models and champion MMA fighters.

And there are legitimate historical / literary roots for heroes of such mighty adventures and exploits, these are your Hercules and Lancelot types, going all the way back to Gilgamesh.

But if you dig just a bit deeper into the historical record, you will find there are quite a few remarkable real people from history who also had adventures seldom matched in any Fantasy Novel, DnD game, or all the WoW games ever played. People who we can relate to, even though they are a long way from the cubicles or home offices of the modern world. In fact, many of the people on the lists you’ll see in a minute were probably greater warriors than Conan, wiser than King Arthur, and more ruthless and intrepid than Elric.

#2) The inquisition and the patriarchy

Another Trope which blocks people from looking for these historically based heroes, is the idea that the past was a time of unbearable oppression and fanaticism, with backward thinking and heavily constrained societies that nobody would want to be part of, if they had any alternative. In other words, not a place fun to explore or play around in. So we prefer a modern fusion which gives us our swords and castles but also allows for the kind of freedom and expression of personal identity we consider the norm today.

Of course, this is a huge can of worms. The past does indeed have many periods of severe repression and social constriction, just as we still in fact do around the world today. But these things came and went over time and in different places, again just like today. The later medieval period in particular was surprisingly loose in the sense of social control, in part because it was so politically fragmented. Nor was this the only time where such conditions prevailed. Even in some of the most repressive societies, one finds that people did not simply accept the domination of ideological systems or hierarchies. It’s not that oppression didn’t exist, it’s just that many people found many ways around it. So for example, it is not hard to find fascinating female warriors and badass women who lived remarkable lives of adventure and daring in say, medieval Europe or Japan. You can also find many more people than you might have expected who crossed lines of ethnicity, gender and class (or more properly for the era, estate) to make their mark on the world. Even in the Classical World, or the Early Modern era during the rise of religious sectarianism, these people existed. So if you are looking for someone to anchor an adventure upon, you can indeed find them.

In my opinion at least. Here are just a few examples of what I mean from Europe and the Middle East:

Warriors, Bandits, Pirates, Rebels, Explorers, Mercenaries, Conquerors

In rough chronological order: These are the ‘B’ players, most are not household names (at least in the US) though some are quite well known in their own parts of the world. Not kings or emperors in most cases, but people from the middle or even lower ranks of society who rose to achieve greatness. I put an estimated alignment next to each entry, for greatness in this context does not necessarily equate with virtue, so if you are looking for someone you might sympathize with or find interesting, maybe that will help. Some of these people were good, some are thoroughly evil, most were neither or both.
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Criteria: Traveled to exotic lands, lived a life of adventure, conquered great nations, triumphed against impossible odds, lived a long time despite constant danger, displayed multiple talents, demonstrated phenomenal skill as a warrior or military leader (often clearly the best in their generation), showed remarkable pluck, humor and / or creativity, broke tradition and pioneered new innovations.

Most important: regardless of where they started in life, these people transcended expectations and the limitations of their position, and went far beyond the achievements of their peers.

Artemisia of Halicarnassus (aka Artemisia I of Caria), 5th Century BC N

Greek queen, tyrant, naval commander, political advisor. A female pirate queen who fought on the wrong side of the battle of Salamis (for the Persians) but escaped to fight another day
Artemisia I of Caria – Wikipedia, the free encyclopedia Blog post about Artemesia

Xenophon, 431-355 BC (96 years old) LN

Greek soldier, mercenary, author, historian, tactician, philosopher, and horse whisperer. Fought his way out of deepest Persia with 10,000 Greek Mercenaries and lived to tell the tale
Xenophon – Wikipedia, the free encyclopedia

Queen Teuta of Illlyria CN

3rd Century BCIllyrian Female pirate queen and naval commander
http://en.wikipedia.org/wiki/Teuta

Pytheas of Massalia, 380-310 BC (70 years old) N

Greek merchant, geographer, and explorer
Pytheas – Wikipedia, the free encyclopedia
‘Discovered’ British Isles (‘pretania’) and “Thule”

Viriathus the Lusitani, 180 BC – 139 BC (59 years old) CG

Celtic warrior, guerilla leader, rebel – confounder of the Roman Empire

Viriathus – Wikipedia, the free encyclopedia

Spartacus, 120 BC – 70 BC (50 years old) CG

Roman gladiator, slave, rebel, bandit, warrior – pain the Roman Empires ass

Spartacus – Wikipedia, the free encyclopedia

Josephus (aka Flavius Josephus), 37 – 100 AD (63 years old) LN

Hebrew guerilla, warrior, Roman collaborator, author, historian, math whiz
Josephus – Wikipedia, the free encyclopedia

Charles Martel, 686 – 741 AD (55 years old) NG

Frankish aristocrat, warlord, general
Charles Martel – Wikipedia, the free encyclopedia

And in the shock of the battle the men of the North seemed like a sea that cannot be moved. Firmly they stood, one close to another, forming as it were a bulwark of ice; and with great blows of their swords they hewed down the Arabs. Drawn up in a band around their chief, the people of the Austrasians [sic] carried all before them. Their tireless hands drove their swords down to the breasts of the foe.”

Pelayo of Asturias, 690-737 AD (47 years old) LN

Visigoth nobleman, Spanish guerilla leader, founder of the Kingdom of Asturias
Pelayo – Wikipedia, the free encyclopedia

Bjorn Ironside (aka Björn Järnsida ), 9th Century AD CN

Swedish chieftain / jarl, resourceful pirate leader, Viking, warrior
Bjorn Ironside – Wikipedia, the free encyclopedia

Gange-Rolf (aka Rollo of Normandy, aka Ganger Rolf, aka Hrólfr Rögnvaldsson and Göngu-Hrólfr), 860-932 AD (72 years old) N

Norse Viking, pirate, bandit, soldier, duke of Rouen, founder of Normandy
Rollo – Wikipedia, the free encyclopedia

Ethelfleda 872-918 AD LG

Female Saxon warrior, military leader, anti-Viking and privateer
http://en.wikipedia.org/wiki/Ethelfleda

Egil Skallagrimsson, 910-990 AD (80 years old) CN / CE

Norse Viking, poet, sorcerer, skald, pirate, duelist
https://en.wikipedia.org/wiki/Egill_Skallagr%C3%ADmsson


Egil is the great anti-hero of Icelandic literature, known for breaking his oaths, killing for trifles, and practicing sorcery. Many historians consider Egil to be one of the deadliest men that ever lived in bladed combat- several accounts tell of him slaughtering as many as 20 or more armed men single-handedly, and even dispatching a feared berserker with relative ease. In spite of this, he was considered a great healer, and his saga tells of him curing a girl who had been ill for quite some time where all other efforts had proven futile.”

Aud the Deep-Minded, 834-900 AD LG

Norse noblewoman, one of the founding settlers of Iceland
Aud the Deep-Minded – Wikipedia, the free encyclopedia

Ahmad ibn Fadlan, 10th Century AD LN

Arab writer, diplomat and traveler who visited the Vikings, the Germans and the Slavs
Ahmad ibn Fadlan – Wikipedia, the free encyclopedia

Bohemond I of Antioch, 1058 – 1111 AD CN

Norman Crusader, Prince of Taranto and later Antioch. One of the most remarkable of the crusader lords, Bohemond is most famous for his remarkable military exploits, during which he showed his ruthlessness and devious cunning. But he’s also someone who has been immortalized with a very rare (for this time) detailed physical description, as written by the Byzantine princess Anna Comnena:

“Now the man was such as, to put it briefly, had never before been seen in the land of the Romans, be he either of the barbarians or of the Greeks (for he was a marvel for the eyes to behold, and his reputation was terrifying). Let me describe the barbarian’s appearance more particularly – he was so tall in stature that he overtopped the tallest by nearly one cubit, narrow in the waist and loins, with broad shoulders and a deep chest and powerful arms. And in the whole build of the body he was neither too slender nor overweighted with flesh, but perfectly proportioned and, one might say, built in conformity with the canon of Polycleitus… His skin all over his body was very white, and in his face the white was tempered with red. His hair was yellowish, but did not hang down to his waist like that of the other barbarians; for the man was not inordinately vain of his hair, but had it cut short to the ears. Whether his beard was reddish, or any other colour I cannot say, for the razor had passed over it very closely and left a surface smoother than chalk… His blue eyes indicated both a high spirit and dignity; and his nose and nostrils breathed in the air freely; his chest corresponded to his nostrils and by his nostrils…the breadth of his chest. For by his nostrils nature had given free passage for the high spirit which bubbled up from his heart. A certain charm hung about this man but was partly marred by a general air of the horrible… He was so made in mind and body that both courage and passion reared their crests within him and both inclined to war. His wit was manifold and crafty and able to find a way of escape in every emergency. In conversation he was well informed, and the answers he gave were quite irrefutable. This man who was of such a size and such a character was inferior to the Emperor alone in fortune and eloquence and in other gifts of nature”
Bohemond I of Antioch – Wikipedia, the free encyclopedia

Freydís Eiríksdóttir, 11th Century AD CE

Norse explorer, warrior, pioneer, killer
https://en.wikipedia.org/wiki/Freyd%C3%ADs_Eir%C3%ADksd%C3%B3ttir

Isabel of Conches 1100s AD

Female Norman Knight and Noblewoman who fought at the battle of Hastings
Isabel of Conches – Wikipedia, the free encyclopedia

Doge Enrico Dandolo, 1107-1205 AD (98 years old) N / CE

Blind Doge (ruler) of Venice, crusader, military adventurer, conqueror of Byzantium at age 90. One of the most cunning figures of medieval history (and that is saying something) Doge Dandalo is known for having diverted the 4th Crusade from its intended target in Egypt, to the Byzantine Empire, where it achieved the unthinkable capture of Constantinople. In this single act, the city state of Venice was catapulted past it’s former masters and the Byzantine Empire was largely broken.
Enrico Dandolo – Wikipedia, the free encyclopedia

Usamah ibn Munqidh, 1095-1188 LN

Arab knight, politician, author and diplomat. Usamah wrote a riveting first-hand account of his experiences during the Crusades as an Arab knight, with some of the most vivid detailed accounts of personal combat during this era, and many fascinating and amusing anecdotes of life at that time. Usamah was a personal friend of Saladin and also at time worked for some of the Frankish commanders, so he knew what he wrote about.
Usamah ibn Munqidh – Wikipedia, the free encyclopedia

Hangaku Gozen

Another Female Samurai from the 12th Century

http://en.wikipedia.org/wiki/Hangaku_Gozen

William Marshal, 1146-1219 AD (73 years old) CN

English soldier, knight, first earl of Pembroke
William Marshal, 1st Earl of Pembroke – Wikipedia, the free encyclopedia

Alexander Nevsky, 1220-1263 AD (43 years old) LN

Swedish –Russian prince, warlord, soldier, and statesman
Alexander Nevsky – Wikipedia, the free encyclopedia

Tomoe Gozen 1157-1241

A female Japanese Samurai (!!)

Tomoe Gozen – Wikipedia, the free encyclopedia

Roger de Flor (Aka Roger von Blum),1266-1306 AD (40 years old) CN

German templar, pirate, Byzantine Caesar, leader of the Catalan Grand Company
Roger de Flor – Wikipedia, the free encyclopedia

James Douglas (aka “The Black Douglas”), 1286- 1330 AD CN

Scottish knight, guerilla, rebel, and bandit (44 years old)
Earl of Douglas – Wikipedia, the free encyclopedia

Jeanne De Clisson CN

Female Pirate and Breton rebel, scourge of the French Navy
“Jeanne de Clisson, enraged and bewildered over her husband’s execution, swore revenge on the King, and Charles de Blois in particular. She sold off the remnants of the Clisson lands to raise money, whereupon she bought three warships, and the aid of many of the lords and people of Brittany to ensure their independence.“
The ships that Clisson purchased were painted all black on her command, and the sails dyed red. The ‘Black Fleet’ took to the waters and began hunting down and destroying the ships of King Philip VI, and were merciless with the crews. But Clisson would always leave two or three of Philip’s sailors alive, so that the message would get back to the King that the “Lioness of Brittany” had struck once again. Jeanne and her fleet also assisted in keeping the English Channel free of French warships, and it is very likely that as a privateer she had a hand in keeping supplies available to the English forces for the Battle of Crécy in 1346. When King Philip VI died in 1350, it was not the end to Jeanne’s revenge. She continued to wreak havoc among French shipping, and it was reported that she took particular joy in hunting down and capturing the ships of French noblemen, as long as they were aboard. She would then personally behead the aristocrats with an axe, tossing their lifeless bodies overboard.”
Jeanne de Clisson – Wikipedia, the free encyclopedia

Eppelein von Gailingen 1315-1381 (66 years old)

A notorious Raubritter or Robber Knight active in Franconia through the 14th Century. He terrorized merchants and travelers for many years, kidnapping and robbing many, and killing some. He is known chiefly for his single greatest exploit. Captured by the forces of the Free City of Nuremberg, he was taken up to their castle and about to be hanged. He asked as one last favor to be allowed to sit on his horse a final time. As they were up in the castle and his hands were bound, they allowed it. Eppelein put his spurs to the horse and it jumped over the walls and into the moat, enabling him to escape. He was caught again ten years later and killed, but the deed made him famous across Europe for generations.

https://en.wikipedia.org/wiki/Eppelein_von_Gailingen

Bertrand du Guesclin, (aka ‘The Eagle of Brittany’) 1320-1380 AD NG

Breton knight and French military commander (60 years old)
Bertrand du Guesclin – Wikipedia, the free encyclopedia

Sir John Hawkwood, 1320-1394 AD (74 years old) NE

English mercenary leader, condottieri, leader of the ‘White Company’
John Hawkwood – Wikipedia, the free encyclopedia

Klaus Störtebecker 1360-1401, (41 years old) CE

Saxon pirate leader and knight
Klaus Störtebeker – Wikipedia, the free encyclopedia

Jan Žižka, 1360-1424 AD (64 years old) CG

Czech soldier, Hussite military leader, military innovator and rebel. As a youth, Žižka foughtfor the Poles at Grunwald, and for the English at Agincourt. Later when his homeland was threatened by a massive Crusade, he was instrumental in helping the Czech Hussite heretics organize their wildly successful defense including some of the first successful deployments of firearms on the open battlefield.
Jan Žižka – Wikipedia, the free encyclopedia

Braccio da Montone, 1368-1424 AD (56 years old) LN

Italian aristocrat, prince of Capua, condottieri, and military innovator
Braccio da Montone – Wikipedia, the free encyclopedia

Cecília Rozgonyi 1398 – 1434 (36 years old) LG

Hungarian noblewoman, ship skipper and war-leader. She is most famous for an exploit in 1428, when as commander of a small river fleet operating near Golubac fortress, she saved the life of King and Holy Roman Emperor Sigismund, helping him and his men escape across the river during his retreat from the battlefield after the defeat by the Turks at the Battle of Golubac

John Hunyadi, 1387-1456 AD (58 years old) LN

Vlach aristocrat, Capitan-general and regent of Hungary, War Leader and rebel. He rose from the status of a knight in a remote and war-torn corner of the Kingdom to become a king himself, and one of the few warriors of the era with a proven record of success against the Ottoman Empire.
Omnipelagos.com ~ article “John Hunyadi”

Skanderbeg aka Gjergj Kastrioti, 1405-1468 (63 years old) CG

Albanian nobleman, Ottoman war leader, Albanian rebel, guerilla leader, warrior. Among other notable achievements before escaping the Ottomans to launch a rebellion he fought and won a gladiator style, personal combat against a Mongol champion within the court of the Sultan.
Skanderbeg – Wikipedia, the free encyclopedia

Hiawatha, 15th Century AD LG

Iroquois chieftain, warrior, statesman, and orator
Hiawatha – Wikipedia, the free encyclopedia

Hans Talhoffer – 1410-1482 (72 years old) CN

Known today primarily as a fencing master and fight-book author who wrote at least five different treatises on fencing and warfare. Hans Talhoffer was a man of uncertain origin, though probably a burgher, and something of an adventurer who had quite a few scrapes with the law as he rose from semi-obscurity as a hired sword to relative prominence as a courtier to the princes. In the 1430’s Hans was ‘given a horse’ by the city of Nuremberg and became one of their hetzrüden, or ‘staghounds’, enforcing the peace of the road. In 1433 he represented the archbishop of Salzburg before the Vehmic court.

He may have joined the famous fencing guild the Marxbrüder around this time (their emblem of winged lions appeaers in his coat of arms). In 1434 he was arrested for complicity in the murder of a robber knight, and held prisoner by the man’s brother. He became established as one of the first ‘respectable’ fencing masters in the 1440’s with the publication of his first ‘fight book’, and was hired by the city of Zürich in 1454, but summoned before the town council that same year after a fight broke out among his students. Talhoffer lived to old age while working for a series of nobles.

Onorata Rodiana 1472

A really interesting character, a female Italian fresco painter and artist who after thwarting an attempted rape, became a Condotierre (mercenary soldier) and eventually a Condotierre Capitan!

« Onorata nacqui, onorata vissi, ed onorata muoio »
“Honored I was born, honored I lived, and honored I die”

Female Firebrands and Reformers – Onorata Rodiana
Onorata Rodiana
Onorata Rodiani – Wikipedia

Paul Benecke ~1410 – 1480, (70 years old) CG

A town councilor and merchant skipper of the Free and Hanseatic City of Danzig, and later in life a privateer captain fighting under a letter of marque from Lübeck, Paul had a wildly successful career particularly once he became the captain of the mighty Peter von Danzig, a refitted French caravel which became one of the largest and most formidable warships of the North Sea. While commanding that ship, Paul almost single handedly defeated England during the Anglo-Hanseatic War of 1468 – 1474, and during that conflict achieved several remarkable feats of daring. In 1468 he defeated the English fleet at Zween. In 1470, he captured the mayor of London on a ship in the English Channel. In 1473 he captured the Florentine galley St. Matthew as it was leaving port in Bruges. Among other treasures that ship (owned by the Medici bank) was carrying the famous Hans Memling Tryptich The Last Judgment which is still held by Danzig / Gdansk.

https://en.wikipedia.org/wiki/Paul_Beneke

Johannes Grant (1453)

A Scottish mercenary in the employ of the city-State of Genoa, who shows up in the records of the siege of Constantinople in 1453. He was a tunneling expert who successfully defeated Ottoman efforts to tunnel under the great walls of that city, famously using water barrels to check for subterranean vibrations. He may have also been a miner. Few records about him exist other than those from Byzantium but he is believed to have escaped the city with some of the Genoese forces before the collapse of the defenses and sack of the city.

https://en.wikipedia.org/wiki/Johannes_Grant

Jan Jiskra of Brandýs ~1400- 1469 (69 years old) CN

Aka John Giskra. A Moravian Czech noble, mercenary contractor and warlord, Lord of Upper Hungary and founder of the nation of Slovakia. A really colorful character known for his ability to ‘wrangle’ dangerous Hussite heretic mercenaries, who were both feared and in high demand for their ability to successfully contend with Ottoman armies. He gained control of the mining towns of the mountains in what was then Northern Hungary (now Slovakia) and helped establish it as a haven for Czech, Moravian and German miners, and Czech mercenaries. He clashed several times with John Hunyadi and defeated him and other warlords, before briefly being forced out of Hungary. He was later invited back in to help control the Hussite mercenary bands who had proven impossible to defeat or drive away, later becoming allied with his son Matthias Corvinus against the Turks. Jiskra also fought in the 13 Years War between Poland and the Teutonic Knights and several times acted as a diplomat, helping to negotiate treaties there and in Hungary.

https://en.wikipedia.org/wiki/John_Jiskra_of_Brand%C3%BDs

Didrik Pinning ~1430-1491 (age 61)

German burgher, privateer captain, pirate, explorer and later admiral of the Danish navy. Didrik Pinning started out as a fairly typical privateer skipper, if there can be said to be such a thing, working in the service of Hamburg. He raided English pirate and merchant ships in the North Atlantic during intermittent conflicts between the Hanse and England in the 1460’s. In 1469 he was hired by the Kingdom of Denmark and turned against his former masters in the Hanse. He won a reputation as a pirate. In 1476 he made a famous trip to Greenland, and some people claim he made it all the way to North America.  In 1478 he was made governor of Iceland, from where he continued voyages of exploration and privateering. In 1481 he was knighted and his coat of arms included a grappling hook. From 1484 he became an important commander for Denmark during the Anglo-Danish war of 1484-190. He captured 3 Spanish ships in 1484, captured the island of Gotland for Denmark in 1487.

https://en.wikipedia.org/wiki/Didrik_Pining

Pierre Terrail, aka seigneur de Bayard 1473-1524 (51 years old) LG

French knight, military leader, considered one of the most accomplished knights of his day.
Pierre Terrail, seigneur de Bayard – Wikipedia, the free encyclopedia

Grutte Pier (aka Pier Gerlofs Donia)1480-1520 (40 years old) CN

Frisian Pirate, revolutionary
Pier Gerlofs Donia – Wikipedia, the free encyclopedia

Götz von Berlichingen (c. 1480 – 23 July 1562; unabbreviated form: Gottfried von Berlichingen)

A German knight (Deutscher Ritter), Raubritter, and Mercenary. With one mechanical iron hand. Another truly incredibly colorful figure, known for a famous vulgar quote uttered during a siege, quoted by Goethe and Mozart, he once led a peasant rebellion and on other occasions repeatedly raided and harassed the mightiest Free Cities of the Rhineland and Swabia.
Gotz von Berlichingen – Wikipedia, the free encyclopedia

Bernal Diaz, 1492-1584 AD (92 years old) LN

Spanish conquistador, soldier, author
https://en.wikipedia.org/wiki/Bernal_D%C3%ADaz_del_Castillo

John of Austria, (aka Don Juan) 1547 – 1578 AD (31 years old) LG

Austrian noble, admiral
John of Austria – Wikipedia, the free encyclopedia

Gráinne Ní Mháille, 1530 – 1603 AD (73 years old) CG/CN (Depends who you talk too)

Called Grace O’Malley by the English and also called “The Sea Queen Of Connaught”, she was an Irish noblewoman, pirate, mother, and clan leader. Well educated, she famously had an audience with  Queen Elizabeth the Ist, which ended in a treaty.
Grace O’Malley – Wikipedia, the free encyclopedia

Duarte Fernandes and Blas Ruiz, 16th Century

Duarte Fernandes was a Portuguese tailor who was part of one of the first Europeans to visit the Kingdom of Siam (Thailand), in 1511. After taking part in a mutiny, he was spared due to his ‘amiable nature’ and later send as an ambassador to Siam, where he was successful in his mission and helped establish friendly relations with the Portuguese colony in Malacca. He took a specific interest in Chinese shipbuilding and was fascinated by the Chinese junk.

Blas Ruiz, a Spanish sailor and possibly a minor noble, in addition to being part of the above adventures, he instigated the ill-fated Spanish invasion of Cambodia, in another attempt to restore their friend King Sathah to power. Interestingly, the Spanish sent 3 ships with Spanish, Filipino Japanese and Mexican soldiers. Blas Ruiz was probably killed by Malay mercenaries in the hire of King Satha’s son and rival.

William Adams, 1564-1620 AD (56 years old) LG

English samurai, shipwright, pilot, navigator, sailor
William Adams (sailor) – Wikipedia, the free encyclopedia

Miyamoto Musashi, 1584 – 1645 AD (61 years old) CN

Japanese samurai, duelist, fencing master, author, artist and philosopher
Miyamoto Musashi – Wikipedia, the free encyclopedia

Catalina de Erauso (1585-1650)

Basque Female soldier, assassin, conquistador, duelist
Catalina de Erauso – Wikipedia, the free encyclopedia
Destreza Translation & Research Project

Sir Kenelm Digby, 1603-1665 AD (62 years old) LG

English gentleman, privateer, scientist, alchemist, Catholic activist, author, duelist
Kenelm Digby – Wikipedia, the free encyclopedia
The Extraordinary Street Fight of Sir Kenelm Digby

Anne Dieu-le-Veut

Female French pirate 17th Century CN
“In 1683, Anne’s husband was killed in a bar fight by the famous buccaneer Laurens de Graff. She challenged Laurens to a duel to avenge her husbands death (other sources claims she heard him insult her), and while Laurens drew his sword, Anne drew her gun.”
http://en.wikipedia.org/wiki/Anne_Dieu-Le-Veut

Mai Bhago (late 17th century) LG

Female Sikh warrior and military leader
http://en.wikipedia.org/wiki/Mai_Bhago

Henry Morgan, 1635 – 1688 AD (53 years old) CN

English / Welsh soldier / sailor, pirate / Buccaneer / Privateer
Henry Morgan – Wikipedia, the free encyclopedia

Julie d’Aubigny (aka “La Maupin”), 1670-1707 AD (37 years old) CN

French aristocrat, swordswoman, duelist, storyteller, outlaw and opera singer
Julie d’Aubigny – Wikipedia, the free encyclopedia
http://home.comcast.net/~brons/Maupin/LaMaupin.html

Donald McBane, circa 1670 ? -1730 AD ? (60 years old) CN

Scottish adventurer, fencing master, soldier, pimp, tobacco spinner et al
History : The Expert Swordsman : The Royal Scots – The Royal Regiment

https://en.wikipedia.org/wiki/Donald_McBane

Thomas-Alexandre Dumas 1762 -1806 (44 years old)

French Revolutionary war general, cavalryman, and fencer, father of the author of the Three Musketeers. He was a political rival of Napoleon.

https://en.wikipedia.org/wiki/Thomas-Alexandre_Dumas

Jean Louis Michel 1785-1865, (80 Years old)

Arguably the greatest single fencer who ever lived. A soldier in the French Army in the 18th and 19th Century and later in life a famous fencing instructor. He was of African heritage, and his fame came about as a result as an unprecedented organized mass duel between two regiments of the French army in Spain.

https://en.wikipedia.org/wiki/Jean-Louis_Michel