Why Good Leaders Go Bad: What Benedict Arnold Can Teach Us About Ego, Isolation and Leadership

You were probably just thinking that it would be really great if someone did a high-level leadership study of Benedict Arnold to better understand why seemingly talented leaders can still fail horribly, weren’t you? Well, you’re in luck. 

This story was originally published on Medium.

As my fascination with Revolutionary War-era America continues (I recently spent a day off on a walking tour of lower Manhattan devoted to exactly that), the natural heroes and villains of the era emerge. George Washington? Hero. Benedict Arnold? Villain. But of course, history isn’t actually that simple, and the labels we give our predecessors tend to obscure them into one-dimensional oil paintings rather than living, breathing, complicated human beings. One book that does a phenomenal job of examining this further is Valiant Ambition: George Washington, Benedict Arnold and the Fate of the American Revolution. Spoiler alert: We won. Additional spoiler alert: Arnold was a good guy - up until the end. 

Good, in this case, is relative. Benedict Arnold was a highly polarizing figure who either drove men to loathing or drove them to follow him with blind loyalty to the ends of the earth (in this case, the ends of the earth started with Canada during the French and Indian War). Pick him up and drop him into modern times, and he’s the stereotypical CEO. Beloved by some, hated by others, undeniably brilliant and talented at what he does. And what Arnold does is fight. He’s arguably the best commander the Continental Army has, and frequently throws himself into harm’s way in the name of victory. He has numerous flaws, but they’re all looked over and cast aside when the right man is needed for the job. This, somewhat understandably, gives Arnold one hell of an ego. 

Ego is not necessarily a bad thing. Particularly when your job hinges on projecting confidence. No one trusts a commander who doesn’t seem to trust himself, just like no one trusts a business leader who doesn’t seem to trust themselves. Displaying doubt in front of the troops, whether they be a rag-tag group of militiamen or employees at a startup or Fortune 500, weakens morale and increases dissent. Dissent borne of healthy debate and educated conversation is good. Dissent borne of doubt in the ability of the army or company to survive? Bad. 

But Arnold’s ego went too far. It caused him to become self-serving and greedy, making only the decisions that were best for him because he didn’t believe congress or Washington truly appreciated him. And look, they probably didn’t. He was passed over for promotions in favor of those less qualified because of politics. He was told “no” time and time again to requests that should have been met with a “yes”. But where he could have chosen to make amends, he instead chose to fester in anger. His pride wouldn’t allow him to compromise or “get over it” to continue serving his country. He was right. They were wrong. And he would not listen to any voice that suggested otherwise.

And what happens when a leader feels overworked, under-appreciated, abandoned by those thought to be allies, and 100% certain that they are right and everyone else is wrong? They isolate themselves. There came a certain point when Arnold stopped communicating effectively (not that he was ever a whiz with words) with those whom he once counted as friends and determined to shut himself in with his righteous indignation at being looked over by congress. 

He wanted to fight, they gave him the military governorship of Philadelphia instead. He wanted to be taken seriously, they made him the subject of jokes and nasty rumors (not all of which were untrue). And so, to his mind, he was only further proven right - the continental congress was not be trusted. Washington was not to be trusted. He was laying in the bed that he himself made, but he couldn’t see past his own version of the truth. He, Benedict Arnold, had been wronged. And those who wronged him deserved to lose. 

The rest, as they say, is history. Benedict Arnold turned and promised the British that he could deliver them West Point on the Hudson River. The attempt failed, he escaped, and ultimately lived out the rest of his days in England after America won the war. The wasted potential is infinite. Arnold went from being a mercurial, worshipped American war hero to someone whose name is still synonymous with betrayal and cowardice even 240+ years later. No matter what good he did during his early days on the Canadian frontier, or at the Battle of Saratoga, railing against the world-famous British Navy. He couldn’t see past himself and what he believed he was owed. An unchecked ego, combined with isolating himself from those who were once his allies, turned him from hero to villain. 

So, what exactly does that tell us outside of the life-and-death context of 18th century warfare? Simply put: we’ve all got a little bit of Benedict Arnold within us. Our egos get bruised, we shut down in the face of criticism, we hold on too long to perceived wrongs or make up our minds that we are right and refuse all evidence to the contrary. It was a recipe for disaster in warfare, and it’s a recipe for disaster in business leadership. 

The same qualities that made Arnold such a brilliant leader also caused his downfall. Too much of a good thing, as it were. And so I’d like to think Arnold can teach us when to get out of our own way. When to get over ourselves, no matter how vital we view our “mission” to be. When to reach out to a colleague or mentor instead of shutting down or simply removing dissenting voices from the room. Successful leadership, particularly in current times, requires a high level of self-awareness and emotional intelligence - two things that Arnold never quite seemed to master, and more importantly, two things that he didn’t seem to think mattered at all. 

So the next time you find yourself faced with a challenging business decision, ask yourself this: What would Benedict Arnold do? And then give some serious thought as to whether or not you want to model your decision-making after his.