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How a Band of Pirates, Militiamen, and Braves Literally Saved America

The best-selling author of Dream Teams reveals what we can learn about the science of teams from America's strangest team of misfits.

The story of Andrew Jackson and his misfit army teaches us that we don’t need to be alike to be united, we just need to be working towards a superordinate goal.

Requiring adherence to strong values promotes organizational silence: employees in companies with strong values tend to hush up when their opinions are at odds with those of their superiors.

Shared values help us come together, but effective teams need to have different perspectives to encourage creative problem solving. 

Shane Snow is the bestselling author of Dream Teams and Smartcuts. Currently, Shane is the CEO of the film tech company SHOWRUNNER, which helps filmmaking teams work smarter together. (Disclosure: SHOWRUNNER is an A.Team Customer.)

In All-Time A.Teams, we examine the greatest teams of all time, and the teamwork lessons we can learn from them. This week, Shane Snow shows us what we can learn about the power of subordinate goals and shared values from America's most unlikely dream team.

In the early 1800s, Great Britain came up with a plan to reclaim America as a colony. The only thing standing in the way was a raucous, booming port city called New Orleans. This was due, in large part, to a couple of local heroes: the pirate brothers Jean and Pierre Laffite.

Jean was six-foot, dark haired, and sexy. Far from the modern peg-leg caricature, he was a fancy dresser who spoke elegant Spanish, English, and Italian. Jean resisted the term “pirate,” preferring “captain” or “privateer.” His older brother Pierre ran the New Orleans blacksmith shop that served as their smuggling front. Their older brother Dominique You sailed a fleet of ships around the Caribbean looking like a straight-up pirate—striped pantaloons and all. The Laffites raided foreign ships and trafficked in fine silks, Moroccan rugs, ornate silver, whiskey, rum, and wine.

These were complicated fellows.

In the early 19th century, hijacking someone else’s boat was legal if your country was at war with their country. Cleverly, the Laffites sailed under letters of marque—a sort of mercenary license-to-kill—granted by the city-state of Cartagena, which conveniently happened to be at war with everybody.

Importing and selling said plunder in the United States, however, was illegal. So the Laffites set up camp on a couple of swampy islands in Barataria Bay, south of New Orleans. There they would take in ships with plunder, load their goods on rowboats, and sneak them into the city through the bayous.

The city of New Orleans left Barataria alone. So long as it let the Laffites have their little Pirateland, the city would never run out of rum. But the brothers stockpiled gunpowder and cannonballs anyway, just in case.

On the surface, these pirates didn’t exactly seem like selfless helpers people could count on. But in the right situation, that can work to your advantage. Dream teams are often reactors full of different kinds of particles crashing together. Progress requires people. And that often means putting together coalitions—teams of teams.

It turns out a few of our common ideas about team unity are backward. In this article, we’ll unpack how a ragtag band of misfits defeated a military machine to save America during the War of 1812. And along the way, we’ll explore what it takes to assemble volatile contributors into a great team.

Getting the gang together

As the English navy started planning its invasion of New Orleans during the war, British colonel Edward Nicholls made a secret trip to Barataria to meet with Jean Laffite.

On paper, the British navy had an incredible manpower advantage. Nicholls & Co. came with 20,000 troops, plus another 2,700 sailing close behind. But getting to New Orleans would take tricky navigation against the twisting current of the Mississippi River. To get their slow-moving ships upstream, they would need to disable the city’s outer defenses via a ground invasion. And this meant finding a good way for tens of thousands of soldiers to get through a maze of swamps.

Progress requires people.

Nicholls offered Laffite the modern-day equivalent of $2 million to guide his troops through the swamp. Laffite agreed but told them he’d need two weeks to get his affairs in order. Pleased, Nicholls and his men returned to the fleet to prepare.

Once they were gone, Laffite promptly went to the Louisiana government and told them of the Brits’ plan.
Ironically, the state was trying to get rid of the pirate brothers. Since New Orleans hadn’t been doing anything to stop them, Louisiana Governor William C.C. Claiborne had offered a $500 reward for “the capture and delivery of Jean Laffite.”

Pictured: The handsomest pirate fugitive in New Orleans

Cocky as ever, Laffite countered by posting handbills across the city, declaring an even larger reward for the capture and delivery of Governor Claiborne. The state retaliated by sending a schooner of war to clear out Barataria. At the same time Laffite was double-crossing the British, the pirates were busy hiding their cannons and treasure in the swamp.

Why the pirates would help the government–their enemy–over the British, was curious. But New Orleans was home, and Laffite loved America.

Upon learning of Colonel Nicholls’s plan, the U.S. government freaked out. America had never planned to defend the Mississippi. Without a strong military presence, the best President Madison could do was call up a lawyer-cum-militia commander from Tennessee who was known for waging war with native tribes: Andrew Jackson.

Jackson was complicated. He was known for his fiery temper, stubbornness, and unwillingness to compromise. These traits did not always square up. For example, one time he nearly killed the Tennessee state governor in a duel over an insult.

Jackson showed up in New Orleans with a bad case of dysentery and his arm in a sling. The city’s entire defense consisted of a makeshift battalion of 287 local lawyers and businessmen, two regiments of poorly equipped Louisiana State Militia, a feisty contingent of local prostitutes who’d volunteered for sewing and ammo duty, and 107 cavalry.

There was also a militia battalion of 210 freemen of color in the area. They had not been paid in a while, but Jackson persuaded them to join. To round out the army, Jackson brought in 1,800 unshaven Tennessee volunteers with hatchets and hunting rifles, known as the “Dirty Shirts.”

But Jackson knew this wasn’t enough.

This was the team that had to take on 20,000 trained Britons? None of these volunteers had ever fought together. Few had ever seen a real battle. They were like a motley crew of young startup kids trying to take on Microsoft. Except the stakes were much bigger than tech dominance. They were betting their lives, their city, and the future of the United States.

Two additional groups of fighters were available, Jackson learned. One was a crew of 62 Choctaw braves. The other, to his dismay, was a gang of criminals who happened to own a lot of cannons: the Baratarians.

Jackson hated the French. He hated the Creoles. He hated criminals. As a slave owner and Creek War vet, Jackson was hardly on the right side of history when it came to black people or American Indians. And Jackson really, really hated pirates.

But he hated the British more, so he agreed to meet with Jean Laffite.

Jackson was charmed by the mustachioed privateer. In addition to cannons, Laffite had stockpiled flints, gunpowder, rifles, and pistols. Jackson made his case for setting aside differences to save the city, and Laffite signed on as the army’s co-strategist.

The Choctaws joined up as well, and the New Orleans defense force became the most diverse group of soldiers ever to fight together in the history of America. They were still outnumbered at least six to one.

They were like a motley crew of young startup kids trying to take on Microsoft. Except the stakes were much bigger than tech dominance.

The British ferried their army through the bayous and camped a few miles south of New Orleans, intending to attack Jackson’s ramparts by day. During the night, however, the Baratarians floated a ship downriver with the lights off and parked across from the British camp. The British noticed, hailed, fired some warning shots at it, then decided it must be a fisherman or something. Tired from rowing through the swamp all day, they went to bed.

Suddenly the gun ports snapped open, and the pirates opened fire on the camp.

The British hadn’t anticipated needing artillery in this battle. The winds wouldn’t allow them to bring their ships upriver for weeks. It would take days to bring ground cannons through the swamps to counterattack the ship. So the army dug trenches, hid in the mud, and waited.

Meanwhile, the Choctaws started sneaking around the swamp and tomahawking British sentries. At the same time, the Dirty Shirts used their hunting rifles to assassinate pickets from afar.

The British officers thought it terribly unchivalrous. Nicholls sent a messenger under a flag of truce to request that they stop this nonsense and fight like gentlemen. Jackson replied with a cordial request that the invading colonel go f*ck himself.

The only way the British could avoid the pirates’ harassing fire was to try to storm Jackson’s line with brute force.

But by the time the British finally charged, the Americans had dug a giant moat and thrown up dirt ramparts several feet high. Behind the wall, Jackson placed the Dirty Shirt riflemen and Baratarian cannoneers, led by Jean’s brother Dominique You.

Photo credit: US Army. There's ... a lot going on here.

The final attack came on January 8, 1815. As the endless horde of British soldiers charged, the motley crew of American defenders opened fire. There was so much smoke that they had to periodically stop shooting and let the air clear so the Dirty Shirts could aim their sharpshooter guns.

When the dust cleared, the British had suffered 3,750 casualties. The Americans had only 333.

This was going to be too hard, the British decided. They packed their things and trekked back through the swamp to their boats.

The British ships went home. New Orleans threw a party.

The Battle of New Orleans went down in history as one of the most brilliant feats of military strategy ever. The outcome was due, in large part, to overconfidence on the part of Colonel Nicholls and his fellows. Yet despicable as he often was, General Jackson deserves some applause as well. Working with people he typically despised, he turned a squad of misfits into a dream team.

The British ships went home. New Orleans threw a party.

The real story of this victory is not about Jackson’s leadership. What ultimately saved the day was an array of fighting heuristics and diverse perspectives.

For example, the Dirty Shirts’ hunting rifles could shoot farther and straighter than any British gun. The Choctaws destroyed the morale of the British troops (not to mention their scouting eyes and ears) with their nighttime assassinations. And without the Baratarians’ cannon work or Laffite’s strategic advice, Jackson was certain his line would have fallen to the enemy.

The power of the superordinate goal

The story of Jackson and his misfit army points us to an important question: How much do dream teams need to be united?

Jackson and Laffite were nothing alike. Yet their heads combined to form a defense strategy that turned overwhelming odds into a resounding military victory. The Choctaws and the Tennesseans were outright enemies. Working together they were unstoppable. The battalion of free blacks built ramparts and shot rifles alongside slave owners who they had every right to hate. The Baratarians manned cannons with the very soldiers who’d been sent by the governor to break their colony up. Together, they all formed an incredible coalition.

What ultimately saved the day was an array of fighting heuristics and diverse perspectives.

In other words, we don’t need to be alike to be united. We don’t even need to like each other. We just need a common cause we all want more than anything else—in this case, a collective enemy and the mission of saving the city.

Psychologists call this a “superordinate goal.” Startups tend to call it a mission.

A superordinate goal isn’t just a common goal. It’s one that takes precedence over all others. For instance, you’d like America to remain a free country more than you’d like $2 million. These are the kinds of goals that get us to overcome our usual hang-ups about collaborating.

History shows time and time again that superordinate goals—or a great mission—have the power to unite even enemies. As the old Sanskrit proverb summed it up more than 2,000 years ago, these hostile parties realized that “the enemy of my enemy is my friend.” Everyone’s desire to keep their home superseded their desire for British gold, or their desire to get revenge. Their superordinate goal brought them together.

It looks like the answer to our question about becoming a united group is simple. No matter how different we are, if we develop a superordinate goal, then we can work together without falling apart.

Except for one little problem: what happened to Jean Laffite after the Battle of New Orleans.

The upside of shared values

On February 6, 1815, President James Madison pardoned the Laffites and their men for any crimes committed before the war. The Baratarians had donated their weapons to save America and fought bravely.

But Louisiana soon turned on Jean Laffite. The state government seized the Baratarians’ possessions. Now that the existential threat was over and American shipping was back in business, they didn’t need the Baratarians. Claiborne even made him a wanted man again.

We don’t need to be alike to be united. We don’t even need to like each other. We just need a common cause.

After the battle, Jackson’s loyalties dissolved as well. He began quarreling with the local government almost immediately. Jackson had imprisoned a meddlesome federal judge when he put New Orleans under martial law. Now that the civilian government was back in control, the judge was suing Jackson for wrongful imprisonment.

Furthermore, days after the battle, Jackson publicly executed six volunteer civilian soldiers who had asked to go home. One of them was a Baptist preacher with nine children at home. He begged for mercy, and Jackson gave him none.

In his official reports, Jackson left out the part where the pirates supplied the gunpowder, flints, and cannons that made victory possible. He gave Jean Laffite a brief commendation but downplayed his strategic role in saving the city. Jackson’s personal code prohibited him from giving criminals credit even when it was due.

Laffite never forgave Jackson.

It turns out that superordinate goals, for all their rallying power, can be fleeting. Once the goal is met or changes, parties have little reason to help each other. Thus, a relationship built on a mutual enemy often only lasts as long as the enemy does. In the Battle of New Orleans, the intentions of a whole bunch of different people aligned for a period of time. But when the goal was achieved, there was no glue to hold them together.

A hundred and thirty years after the Battle of New Orleans, a common enemy brought Americans and Britons together in a similar way. The superordinate goal of stopping Adolf Hitler brought them, along with Russia, together. After they defeated the Nazis, the United States and Russia went back to mistrusting each other. But something interesting happened between America and Britain. They solidified a long-term alliance. The two countries had been growing more friendly over the years, and coming together to beat the Nazis cinched the relationship.

This was not because they shared a language and ethnicity. Many historians argue it was because the two countries had something in common that they didn’t with Russia: a strong set of shared values.

A relationship built on a mutual enemy often only lasts as long as the enemy does.

For the most part, America and Britain believed in similar principles of government, theology, and ethics. When the superordinate goal of stopping Hitler forced the United States and England to work together, they realized they had a lot in common and stuck together.

We see this happen in business all the time. Researchers Jim Collins and Jerry Porras point out that successful companies often have “cultlike” values. Companies who talk about shared values a lot will tend to unify their people quickly and effectively. Their missions make it easier for employees to help each other and solve problems. Research shows these companies tend to have low turnover and relatively stable businesses.

As we’ve seen, shared goals help us come together. But what keeps us from falling apart after the existential threat is over?

The limits of shared values

One of the saddest parts of the Battle of New Orleans is what happened to the British 93rd Regiment. This group of 1,100 proud Scotsmen were required to each be over six feet tall. They looked awesome. They wore plaid tartan trousers and marched to the tune of bagpipes.

The British army was the most disciplined in the world. It had a strong culture of shared values: unflinching bravery, unquestioning loyalty, and impeccable obedience. When you received an order, you never questioned and never deviated.

The Scotsmen were among the best at adhering to these values. Until it killed them.

During the battle’s final assault, the 93rd’s commander was shot right after he gave an order to halt. The troops halted. Then they waited obediently for their next order, standing like statues in front of Jackson’s rampart. They were determined to do nothing but “halt” until told otherwise.

Jackson’s men sprung to action. They shot their cannons at these sitting ducks, taking out six hundred men before someone finally shouted, “Retreat!”

Research from Dr. Charlan Nemeth, of the University of California, shows that strong shared cultural values in an organization, despite the stability they bring, can backfire. The stricter the values, the more potential for catastrophic outcomes. “In fact,” writes Dr. Nemeth, “there is evidence that the atmosphere most likely to induce creativity is one diametrically opposed to the ‘cult like.’”

Shared values, she says, make us more likely to think the same, to not question the way the group thinks. This is good for keeping peace but not for solving problems.

Some organizations try to combat this by making “creativity” and “taking risks” values themselves. However, data shows that doesn’t really work. Groups that have a lot of cultural similarity stop searching for better solutions once they have solutions that work. They think they are creative because it’s a value. But, Nemeth points out, “Good intentions and great effort do not necessarily result in creativity.”

Seven out of ten American business employees in companies with strong values hush up when their opinions are at odds with those of their superiors, according to research by University of Southern California professor Warren Bennis. Requiring adherence to strong values, in other words, promotes organizational silence.

As we’ve learned, effective teams need to have different perspectives. And having different perspectives often go hand in hand with having different values. Yet, coalitions that lack shared values, like that of Jackson and Laffite, often don’t seem to last.

Does that mean great teams are doomed to break up?

Fortunately, the answer is no. There’s just a little more to the equation than simply “shared goals” or “shared values.”

To unpack this idea, we’re going to look at some other pirates in my next edition of All-Time A.Teams. These pirates just happen to be teenagers. Stay tuned for more.


Shane Snow is the bestselling author of Dream Teams, from which this story was adapted. Currently, Shane is the CEO of the film tech company SHOWRUNNER, which helps filmmaking teams work smarter together.

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