Few things made 18th century sailors blast a load of grapeshot into their trousers with greater ferocity than the sight of a giant ominous black flag fluttering in the breeze from the mast of a badass warship teeming with unshaven, hook-handed, face-slashing, ball-stomping Pirate ass destroyers. So you can probably imagine what was going through the mind of James Macrae, Captain of the East India Company ship Cassandra when he saw not one, but two Jolly Rogers pulling into the port on Johanna Island and floating towards him on a warm afternoon in August 1720. Macrae and his crew had pulled into port on tiny island off the coast of Madagascar looking to replenish their stores of food, casks of water, and kegs of top-shelf Bacardi, but now they all of a sudden found themselves neck-high in crap without their inflatable water wings.
Macrae hailed another East Indiaman that was in the port, the Cassandra's sister ship Greenwich, but the coward asshole Captain of the Greenwich was like, "so long fuckfaces, I'm out of here… enjoy having your colon annihilated. See you in Hell." Macrae screamed untold obscenities at the Greenwich, even going so far as to fire a volley at her while she ran for her life like a little bitch, but she evaporated in a cloud of smoke like something out of a goddamned Scooby-Doo re-run.
Cassandra now found herself boxed in by two of the Golden Age of Piracy's most successful cutthroats. Fancy, commanded by Edward England, and Victory under Captain John Taylor. Neither of these men were particularly known for being real-life analogues of Barney the Dinosaur, a detail you could probably divine from the fact that they were both murderous fucking pirates who would just as soon pull out your eyes with a claw hammer than piss on you. Macrae and his crewmen weren't exactly hardcore SAS paratroopers with rocket launchers for arms and cybernetic muscle implants allowing them to vault over small dinosaurs with a single ridiculous leap, but they also weren't the kind of fucking chumps that going to sit back and let a group of scurvy assholes eviscerate them with cutlasses either. Macrae unflinchingly ordered his men load their cannons, and as soon as Victory was within range Cassandra turned and blasted her with a devastating broadside.
The initial impact of being pounded by dozens of giant balls sent Victory reeling, and the second cannonade from Cassandra blew off part of her main sail. The Pirates dropped twenty sets of oars into the water in an attempt to row their damaged ship close enough to board Macrae's vessel, but luckily a third volley of lead death blew those oars into splinters. Even this didn't deter the pirates from their mission to slit the throats over every sailor aboard Cassandra, and the now-crippled Victory continued to limp towards them like a shambling undead zombie. Around this time Fancy pulled into range and released a volley of her own at Cassandra. Fragments of the deck hurtled throughout the ship with deadly velocity, killing several of Macrae's men as they furiously attempted to reload their weapons. Before Cassandra could even wheel about for a broadside on this new opponent, Victory had pulled in close enough to unleash a bombardment of her own. Cassandra was getting smacked with more balls than a passed-out sorority girl.
For over two hours Macrae traded fire with Fancy and Victory as these mighty sailing ships pummeled the fucking crap out of each other relentlessly, but the situation aboard Cassandra was becoming increasingly desperate. Her surviving crewmen were now pouring musket as well as cannon fire at the rapidly-closing Pirate ships, but casualties were quickly mounting, and Captain Macrae knew that his men wouldn't stand a chance in close-quarters combat with those bloodthirsty, heavily-armed, battle-hardened motherfuckers. He ordered his ship to sail full-speed towards the shore, where his men could hopefully escape into the dense jungles on the island's interior, but Captain England of the Fancy was quick to realize what Macrae was attempting. Fancy moved to take the angle and cut Cassandra off, but she struck a shoal and became lodged in the sand. Cassandra attempted to go around Fancy, but she too became grounded on a sandbar, wedged into the surf mere feet from the Pirate vessel. From point-blank range, the two vessels exchanged several brutal broadsides, causing more structural damage than an intoxicated Kool-Aid Man. Ammunition was running low on board Cassandra, and even though he had taken a musket ball off the skull and was bleeding profusely from a massive head wound, Macrae still had his men loading the cannons with chains, nails, broken beer bottles, handfuls of rifle bullets, and anything else they could find to shoot at Fancy.
Both ships were almost completely destroyed at this point, and now Victory was limping towards the immobilized Cassandra, unleashing volleys of musket fire and shouting intimidating insults about the crew's collective mothers. When the Pirates on board Victory threw their hooks over the side of Cassandra and prepared to haul themselves on board, Macrae knew that the battle was lost. He was completely outnumbered by bloodlusted motherfucking pirates, and his surviving crewmen didn't exactly resemble the set of Wrestlemania X. He ordered the men to throw a double-load of powder into the cannons, and when they fired their final volley, he used the smoke screen to cover his crew's escape. The men scrambled to their ships or swam to shore, where they then ran deep into the tropical jungle of Johanna Island. Jackass Pirates swarmed over the decks of Cassandra, slashing the throats of any wounded or dying men they came across and plundering the cargo hold of nearly id="mce_marker"50,000 worth of precious goods from India and China.
Unfortunately for our hero, Pirates don't give up that easily - especially after taking a beating like the one Captain Macrae had ever-so righteously lain upon them. Squads of Pirates combed the jungles of the island searching for the Captain and his men, intent on avenging their fallen brethren. Macrae and his starving, war-weary, wounded crew evaded these patrols, living off the land deep in the inhospitable jungle for ten days before Macrae finally decided to say, "fuck it. I've had enough of this bullshit." Then, in one of the most brazen display of brass balls ever recorded, Captain Macrae put on his full dress uniform and strode towards the coast. A large group of Pirates were standing on the docks, completely astonished that the man they had been searching for so intently was now walking right up to them. The Captain confidently marched right up to the Pirate commanders, stated his name and rank, unflinchingly demanded the return of his ship and cargo, and requested safe passage for himself and his crew.
Obviously the Pirate Captains didn't know what the fuck to make of this shit. On one hand, the man standing before them was personally responsible for the deaths of over 100 Pirates while suffering only 37 casualties of his own. Many believed deserved to be tied to the mast and beaten to death with herrings. However, everyone also had to respect the enormous ballsack full of badassitude that Macrae evidently possessed. Luckily as it turned out, quite a few of the Pirates aboard Fancy and Victory had actually once served under Captain Macrae, and they all remembered him as being a fair and just leader who commanded the respect of his men.
Eventually, the Pirates decided that they couldn't possibly commit the cold-blooded murder of man with as much badassitude as Captain James Macrae. They kept his ship, but allowed safe passage for his men, returned one-half of the supplies aboard Cassandra, and sailed off, leaving him with the half-destroyed Fancy. Macrae and his men performed some emergency repairs and then set off with little more than a skeleton crew to operate the ship. For 48 days the starving, dehydrated, half-dead men sailed on a barely-seaworthy vessel, finally reaching Bombay in October 1720, where they were greeted as heroes by the local British administration. For his amazing courage, Captain Macrae was promoted by the East India Company and eventually became the Governor of Madras, an extremely prestigious post within the British Empire. While in office he fought corruption, and eventually retired to Scotland an incredibly wealthy man. One year after this battle, Captain John Taylor would use Macrae's ship, Cassandra, to capture the single greatest pirate treasure in history – stealing $2 million worth of diamonds and goods from some jackass Portuguese Count. Taylor, a badass in his own right, would receive a pardon from the Spanish Crown and retire to live a life of luxury in South America.
Captain James Macrae wasn't a hardcore cutthroat pirate sailing the seas, plundering enemy ships and slashing Spanish sailors' guts out with a fishing gaffe made out of gold doubloons - he was a regular man who found unbelievable testicular fortitude at a time when most men would have just urinated themselves and ended up having their severed heads used for decoration by a crew of hardcore Pirate motherfuckers. He didn't hesitate to stick it to those Pirate bastards, didn't back down when he faced odds that would have left most people cowering, he whipped his group of civilian sailors into a force that inflicted three times the number of casualties they received, and he put forth an amazing display of bravery so balls-out that it bordered on foolhardiness. Totally badass.
Edward England's Wikipedia Page (There currently isn't one for Macrae)
Botting, Douglas. The Pirates. Time-Life Books, 1978.