The Town, Leadership, and Corporate Corruption


*Spoiler Alert for the movie The Town*

Have you seen The Town with Ben Affleck and Jon Hamm? I loved that movie for 100 reasons including Affleck’s abs and Jon Hamm’s everything.

You should write a script about paint drying and cast it with handsome men. You would make a mint. I’d go and see it.

The movie is about a white-boy-thug with a heart of gold (sorta) who has to pull off one last heist before he quits his life of crime and moves away with a girl of his dreams.

I got it. I’m there. The plot makes sense.

But because I worked in Human Resources and I give out career advice, I suddenly found myself watching a movie about a guy who is haunted by his working class roots. Although Affleck’s character is supremely talented and knows how to organize complex bank heists and launder stolen money, his access to a decent education (and thoughtful role models) means that he lacks opportunities and his skills are squandered. He knocks off banks and hangs out with white-trash urban hooligans because he pulled himself up by his bootstraps and this is still the best he can do.


The movie reaches its climax when Affleck’s character participates in a robbery that is organized by the Irish ‘godfather’ of his working-class neighborhood. Affleck doesn’t like the godfather — played by Pete Postlethwaite — and when the heist goes badly, Affleck’s character reaches a state of enlightenment and a state of fury. It’s fascinating to watch his character’s face. Knowing that the cycle of violence and crime starts and ends with the ‘godfather’ in the neighborhood — a man who is a baby boomer and runs the neighborhood like it’s his kingdom — Affleck kills him.



I left that movie thinking about how corporate leaders act like kingpins. Fiorina. Hurd. Ellison. Whitman. Skilling.

Leadership has corrupted a generation of men and women who started out with good intentions and became greedy & selfish. The generation is lost to the ages. They’re done. They are over. All that’s left for them to do is get richer, fatter, and then die.

A younger generation will supplant those leaders using the same exact tactics that the old guard used to gain power — much like Ben Affleck had to kill Pete Postlethwaite in The Town. That’s how you do it, by the way. Having seen multiple CEOs replaced in my career, and having watched three CHROs lose their jobs, I know that corporate leaders are undone by smart and savvy minions. These minions grow close. They watch, learn, and mimic. When the time is right, they stab their leaders —  Julius Caesar — with the leader’s own Mont Blanc pen.

It’s the stuff of great art.

But when the new generation replaces the old set of leaders, they usually blow it. This is happening right now. Right before our eyes. Think about the Gen X leadership team at Google who aspire to do great things and find themselves moving away from their stance on net neutrality.

Here’s comes the new boss, same as the old boss.


Affleck’s character struggles with creating a new path during the final scenes of the movie. Now that he operates in a new paradigm, he wants  to atone and do things differently. Can he? The Town reminds me that human nature is consistent. Power corrupts. Greed will stifle your conscience. And very few of us, when given the chance, will have the guts to overrun a generation of leaders and kick them to the curb.

And once we kick them to the curb, which is the easy part, we’ll have to take the reins and actually do better.

That’s real leadership, and very few of us are true leaders.

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