Francis Drake was born into an era of conflict. He came from the small town of Tavistock in Devon, in the southwest of England. The sixteenth century was the height of religious conflict in Europe as the Reformation swept across the Continent and Henry VIII divorced his first wife, and in the process separated his kingdom from the Catholic Church. The Drakes’ corner of England remained staunchly Catholic in the face of state-sponsored Anglicanism. When London imposed a change in all church services from Latin to English, the Catholics revolted—and Drake’s father, a Protestant minister, fled with his family.
Young Francis was sent to live with his cousins, the Hawkinses of nearby Plymouth, one of the great English seafaring cities. The Hawkins family had been prominent shipowners and merchants for years, and quickly brought young Francis into the business. The young man took quickly and confidently to the sea—and to the business methods of the Hawkins clan, which made most of its money in illicit trade with the Spanish and Portuguese territories, and not a little more through piracy.
For as long as people have shipped money and goods by sea, other people have put to sea to steal it. From the fictional swashbucklers of Pirates of the Caribbean to the deadly serious Somali pirates of Captain Phillips, the image of piracy has not changed as much as its tactics—it is still a business condemned by the family of nations, illegal under all codes of international law. In Drake’s day, English piracy had not yet entered its semiprofessional golden age of Jolly Rogers and rum-swilling roguery. Rather, it was more of a watery Wild West, in which the line between merchant and pirate was thin and frequently crossed from voyage to voyage, or even in the course of a single sailing. Like the early stagecoach and rail lines of the West, the Caribbean offered many vulnerable, treasure-laden ships and rich settlements to tempt an unscrupulous captain to turn a quick profit at gunpoint.
Drake found his calling in this frontier environment. Sailing with the Hawkinses to western Africa and on early forays into the Caribbean, Drake quickly developed as a sailor—as well as in exposure to the seamier sides of his cousins’ business. During Drake’s apprenticeship at sea, the Hawkinses muscled their way into the slave trade and made a small fortune, shook down defenseless cities, and eluded capture by Spanish warships. Drake learned the thrill of plunder and of the narrow escape, but also how the line between success and failure could be just as fickle as that between merchant and pirate.
One particularly close brush with the Spanish viceroy off the coast of Mexico split Drake off from the Hawkins fleet and launched his solo career. When a hasty escape from the Spaniards precluded much-needed repairs, Drake determined to sail back to England in a barely seaworthy ship. His cousin John Hawkins eventually followed, but only after losing most of his crew as prisoners of war—and learning the true cut of Drake’s brutal methods. On returning to England, Drake promptly went into business for himself. The early results were not auspicious, as he made a series of dangerous and unprofitable raids, lost many of his new crew to disease, and had many close calls with the Spanish authorities. However, Drake soon recognized what he needed to do to succeed as his own boss, and ruthlessly set about doing it. First, he steeled his own will, then drilled his crew to a high state of discipline. Before too long, Drake’s reputation began to rise, both among Spanish colonists fearful of his raiding and English officials impressed by his seamanship.
In Drake’s day, Britannia did not yet rule the waves. That role belonged to Philip II of Spain, then the leading monarch of the powerful Habsburg family, which controlled or exploited much of the Caribbean, Mediterranean, and transatlantic trades. Around the world, Habsburg ships carried Habsburg goods from port to port, creating an enormously lucrative form of proto-globalization to gild the Spanish throne—and a model for England to emulate and exploit. Thus, when Queen Elizabeth commissioned Francis Drake to circumnavigate the globe, the none-too-subtle subtext was a growing English desire to expand their geopolitical reach and compete with the Spanish crown. A round-the-world expedition would not be cheap, but the open secret of its piratical designs on Spanish commerce made it an attractive investment for English businesspeople. Like modern venture capitalists, backers lined up to finance the voyage—including the queen herself. Drake was commissioned as captain of the expedition, and led it from 1577 to 1580.
The small group of raiders under Drake’s command did not even wait to cross the Atlantic before beginning their exploits in 1577. Sailing south from England, they first raided Spanish holdings in Morocco and nearby islands, then turned west and seized vessels in Cape Verde. After the crossing, the fleet continued raiding down the coast of modern Brazil and Argentina. The money piled up, but so did the challenges: once again, Drake was chased by storms and Spaniards, and his hard-driving style of command created tensions with his own people. True to form, Drake drove his crew by the lash of his fury and made them dependent on their captain’s stormy graces. He tolerated no challengers to his authority and took the extreme step of executing his business partner, the nobleman Thomas Doughty, during the brutal passage around Cape Horn. The crew rallied around their captain, but his decision to spill noble blood would haunt Drake for the rest of his life.
Rounding the Cape through the Straits of Magellan, Drake and his crew became the first English sailors to reach the Pacific Ocean, where their brutality would continue to reverberate throughout Spanish America. They plundered and pillaged up the coast of what are now Chile, Peru, and Ecuador, torturing captives and taking whatever they could carry. Reaching the top of South America, Drake and his crew turned west again for the long run across the Pacific. Upon making landfall in the Philippines, they turned south and resumed plundering through those islands and modern-day Indonesia before crossing the Indian Ocean to round the Cape of Good Hope and head north toward England and a hero’s welcome by 1580.
Drake, whose draconian and rapacious tendencies had reached new heights in three years at sea, was promptly knighted for his achievement. Not only was he the first captain to survive a round-the-world voyage (his Portuguese predecessor Ferdinand Magellan had died en route), but his exploits instantly made the humbly born Sir Francis a very wealthy man. He promptly set about the same pursuits as his new peers, becoming mayor of Plymouth, sitting in Parliament, and investing in real estate. He had amassed a fortune and spent money like—well, a drunken sailor.
But Drake’s life was at sea. The queen once again commissioned him to raid Spanish shipping in the Caribbean in the mid-1580s, which he did with great enthusiasm and success. Santo Domingo in today’s Dominican Republic burned. San Agustín (now St. Augustine) in my native Florida burned. His targeted cruelty against Catholic churches conjured images of a Protestant crusader hell-bent on bringing the European wars of religion across the Atlantic. In one particularly brutal attack, Drake stood on the shores of the Caribbean outside the town of Cartagena de Indias on the northern Caribbean coast of Colombia. The city was a commercial hub of Spain’s Latin American empire, and rich with gold. Drake had hundreds of men arrayed around him in the fields near the beach. They carried a mixture of weapons: long pikes, clumsy harquebuses with powder and shot, swords, and cannon. They stood in front of their commander, looking intently at his face. Sir Francis Drake recognized the look: a mixture of eagerness and hesitance, optimism and trepidation. These men were afraid of the battles to come. But more than that, they were afraid of Sir Francis Drake.
In raid after raid, the historical record shows us a commander who bullied and terrified his men. In terms of killing, rape, and pillage, Drake liked to lead from the front, and any of his men who held back were treated worse than the victims in the towns he attacked. A good example was the attack on Cartagena de Indias in which he tasked his men to take the fort at Boquerón (the mouth of the harbor), but watched them fail while under the hesitant command of his second, Martin Frobisher. Drake turned them back to battle, saying he would take the fort if he had to tear the stones down with his own hands. The fire
in his eyes and the threat in his voice had a predictably “inspirational” effect on his men, and they returned to the fray, took the fort, and destroyed the town—the heart of the Spanish Empire in the Americas.
But over time, the Spanish began to understand his tactics and create an intelligence network throughout the Caribbean that often gave them early warning of his approach and intentions. Despite some measure of success in harrying the Spanish treasure ships, his second cruise failed to pay off financially. As a result, Drake lost some of his sheen of invincibility, especially in the eyes of his investors. Even thus tarnished, however, Drake retained the all-important support of the crown. His next mission was to lead a squadron in support of Protestant rebels in the Low Countries who were challenging their Catholic Habsburg masters. The English-Spanish relationship continued on a downward spiral which would soon spill over into open war. Both countries prepared to invade the other by sea; Drake was put in charge of the English efforts, and ultimately determined to strike at the southern Spanish port city of Cádiz. He struck first with a brazen midday attack, which smashed the Spanish merchant fleet sheltering in the harbor. The blow set back the Spaniards’ own preparations for invasion, recovered some of Drake’s prestige, and provided another major financial windfall for Drake and his crew.
Despite the setback, the Spaniards redoubled their efforts to invade England. The new plan called for a massive fleet from Spain to embark an army from the Low Countries and land the troops in England to march on London. The English hastily assembled a fleet to repel this armada, and Drake was named second in command under the aristocratic Admiral Lord Charles Howard. As in the early days sailing with the Hawkinses, Drake distinguished himself as a subordinate by carrying out his assignments with characteristic dash. Drake initially wanted to attack the armada straight out of port, before it could ship the soldiers from the Low Countries, but was overruled by Admiral Howard. Nevertheless, he was typically swashbuckling in coastal defense: ships under his command were often first into the fray, and his crews took risks bordering on foolhardiness. The Spanish Armada could overcome neither the English fleet nor its own poor planning and was forced to return by way of the Scottish coast, where violent storms ravaged much of the remnants of the once-mighty fleet.
Though he shared in the glory of Spain’s defeat and had more adventures ahead, Drake’s best days were already behind him. Further raids on Spain and Portugal proved unsuccessful militarily and financially, and Drake went ashore again in Plymouth. There he took a seat in Parliament once more, and, in an ironic twist, was commissioned by the crown to arbitrate restitution disputes between pirates and legitimate merchants. Finally, he received his last seagoing commission in 1589, ostensibly to take control of Panama but as usual with an open charter to harass the Spanish throughout the Caribbean and South America.
This last Caribbean voyage was star-crossed from the start, and not least by the mercurial habits of Sir Francis himself. Now in his fifties, Drake had hardly changed his leadership style since his twenties, and he continued to lead fearlessly from the front, to drive his crews and himself inhumanly hard, and to chase any apparent opportunity for plunder. He eluded the Spanish until the end, but finally fell victim to the tropics he had terrorized for so long. Drake died at sea of dysentery—an ignominious end for a swashbuckling pirate—on January 28, 1596. Fittingly, his crew sealed their captain’s remains—dressed in full armor—in a lead coffin and committed them to the depths of the Caribbean, whose waters and shores his memory still haunts today. His body has never been discovered.
Throughout his life, Drake’s exploits at sea were defined by his personal physical courage. Whether raiding around the Caribbean, risking the wrath of the more powerful Spanish viceroys; personally leading the second attack on the fort at Cartagena; or aggressively engaging the Spanish Armada, Drake never hesitated to put himself out in front and on the line. While Drake’s personal leadership did not ensure the success of all his exploits, it was always the foundation of the fear and respect he inspired in his crews, victims, and enemies alike.
As Drake’s life demonstrates, courage is a powerful asset of character, but also one that can tempt a leader into trouble. Ferdinand Magellan was hardly less brave, yet his luck did not hold out as Drake’s did, allowing the latter to claim the title of first known global circumnavigator. At many points, Drake’s luck could just as easily have run out—especially when his near-reckless courage put him in a tactically unsound position in the first place. Good leaders know that all the courage in the world can be undone by a bad stroke of luck, or misplaced planning—and they measure their courage. “Live to fight another day” is a good mantra in most settings, and Drake was able to balance his courage and his luck—a good lesson in character.
Even though most leaders today will probably never need to demonstrate physical courage in the ways that Drake did throughout his life, there are many less-swashbuckling ways to exercise courageous leadership. First and foremost among these is moral courage, whether in making a big strategic decision or taking a stand for a deserving person or cause. And like many other qualities of character, courage is a habit that can be developed over time. In the physical sense, there are both psychological and physiological ways to improve performance under stress. Hemingway said that “courage is grace under pressure,” which has been more prosaically rendered as “never let them see you sweat.” Simply taking deep breaths, reflecting on calming settings, telling yourself that you are in control, stretching, speaking in a slow and measured way, and avoiding raising your voice are all physical ways to calm yourself. Another good psychological technique is simply keeping a sense of perspective on whatever you perceive as danger ahead. In all but the direst of circumstances, there is a way to make the situation safer—by concentrating on that, instead of allowing panic to dominate your mind, you have the best chance of reacting with courage as danger threatens.
The first time I faced real danger in a combat setting was in the mid-1980s as the operations officer and tactical action officer in the Aegis cruiser USS Valley Forge. We were operating in and out of the Strait of Hormuz during the so-called tanker war between Iran and Iraq. We would often go to “general quarters” (all hands at their battle stations, four hundred men at tense alert throughout the ten-thousand-ton warship) as we sailed under the range of Iranian missiles and Iraqi attack jets flew overhead. This was about the time that the USS Stark, a US Navy Oliver Hazard Perry–class frigate sailing in these waters, was attacked by an Iraqi jet and nearly sunk. These periods of “general quarters” began with harsh announcements on the ship’s loud sirens (“General quarters, general quarters, all hands man your battle stations”) and would stretch into long hours, broken only by the mess stewards bringing us soup and sandwiches on station. The tension was palpable, and many of the younger sailors were unsettled by the possibility of an actual attack.
Even as a mid-grade officer and a department head (essentially third in command as the operations officer) on the ship, I was scared, nervous that I would make a crucial mistake (I had control over the ship’s weapons system), and above all, I desperately wanted to avoid showing my men my own fear. Fortunately, my vastly more experienced captain (later rear admiral), Ted Lockhart, was able to do all the things I discussed above, plus he had one other endearing habit: he would bring exotic snacks to the Combat Information Center to share during periods of combat alert—everything from French truffle pâté to caviar and smoked oysters. His sangfroid had a wonderful calming effect on us all, to say nothing of the excellent nibbles. Not everyone has the battle experience and bold personality of a Sir Francis Drake (fortunately), but building the habit of courage—no matter the venue—is within everyone’s reach and is part of the voyage of character.
Drake’s management style would have made Darth Vader proud. He ran his crews ragged in search of perfection and quite literally left a trail of bodies behind, having executed scores of his followers for d
esertion and cowardice. He cultivated loyalty by Machiavellian games designed to keep his crews divided against one another and dependent on him. As with his personal drive, Drake’s harsh disciplinary methods are badly out of line with today’s mores—but they got results. Still, even if we grant that times have changed, Drake’s leadership style forces us to confront the extremely uncomfortable question of whether the ends justify the means. In commenting on his discipline, it is necessary to understand the context of his life and times. He was surely not “to the manor born”; he faced enormously difficult physical tasks and was in essentially constant extreme physical danger. Only by understanding those facets of his situation are we able to contextualize and possibly justify his draconian methods. So, adjusting for those factors, what can we learn about character from Sir Francis?
What is most important to remember about Drake’s character in this regard is that he imposed harsh standards of discipline because he was an internally disciplined leader himself. The character lesson, when you strip the centuries-old setting away, is that only a leader who is personally disciplined herself or himself can realistically apply significant discipline to an organization. Nothing succeeds less than an undisciplined leader attempting to apply standards that he or she cannot meet—this evident hypocrisy always fails. It is worth noting that naval history is rife with examples of brutally harsh admirals like Drake; but it also offers inspiring examples of leaders who successfully faced enormous tasks and extreme danger without resorting to the sort of techniques Drake employed throughout his career. (Drake’s countryman Horatio Nelson offers a particularly strong example.) Especially today, when so much has changed in life and work, it is essential for leaders to have the self-discipline to build and maintain healthier team dynamics than Drake did.
Sailing True North Page 6
