The Longest Road to Trouble

You know, I've been in some rather unpleasant situations over the years. I've negotiated with smugglers, argued with armed bandits, and once spent three days in the company of a man who insisted he was the rightful king of somewhere I'd never heard of.

But I'll tell you something.

None of those encounters was quite as dangerous as four friends sitting down to play Settlers of Catan.

Oh, this one's a beauty.

Our story begins with two couples. Jared and Jessy were visiting their friends Luke and Tory for an evening of board games.

A pleasant little gathering. Good company, a bit of friendly competition, and presumably every intention of remaining friends afterward.

They chose Settlers of Catan.

Now, for those unfamiliar, Catan is a game about building settlements, collecting resources, trading with your neighbors, and occasionally discovering that your neighbors are a pack of conniving scoundrels.

All perfectly civilized, of course.

At first, everything went swimmingly.

Resources were collected. Roads were built. Deals were struck.

Jared and Luke, being rather keen strategists, were no doubt contemplating all sorts of clever maneuvers.

Jessy and Tory were enjoying themselves too.

And then something happened.

Something that apparently nobody had adequately prepared for.

Jessy was winning.

Not merely doing well, mind you. She was closing in on the longest road, and victory was looking distinctly possible.

Now, a sensible person might have congratulated her on a game well played.

But Jared?

Oh, Jared had other ideas.

You see, he recognized a threat. And rather than simply attempting to improve his own position, he decided the entire table needed to do something about Jessy.

A little diplomacy. A few carefully chosen arguments.

Nothing terribly dramatic.

Just enough to convince everyone that Jessy was the problem.

Now, I've encountered this sort of fellow before. Usually in a backroom somewhere, explaining why handing over the treasure to him is actually in everyone's best interest.

And the truly dangerous ones?

They're terribly convincing.

So while everyone was busy making sure Jessy couldn't win, Jared was quietly improving his own position.

A road here. A settlement there. A strategically inconvenient obstruction.

All perfectly legal.

All rather clever.

And all while maintaining the appearance of being terribly helpful.

Oh, that's beautiful.

Absolutely rotten, but beautiful.

Because before anyone quite realized what had happened, Jessy's magnificent road to victory had become a road to nowhere.

And Jared?

Jared won!

There you have it. A masterful bit of tabletop maneuvering. He'd identified the strongest opponent, persuaded the others to help neutralize her, and then slipped past everyone to claim the victory himself.

I must admit, I rather admire the strategy.

It's the sort of thing that would make Major Mallory nod approvingly over his campaign maps.

But there's a small complication.

You see, Jessy wasn't merely another player at the table.

Jessy is Jared's partner.

And while Jared may have won the game, he had apparently overlooked one rather important consideration.

Jessy was not especially pleased.

In fact, she was so thoroughly unimpressed by the whole business that she made a decision of her own.

She would never play Settlers of Catan again.

Ever.

Oh, Jared.

You magnificent idiot.

You've won your little island, built your roads, secured your settlements, and conquered the competition.

And in the process, you've managed to convince one of your own companions never to set foot on the island again.

That's quite an achievement.

I've seen expeditions end with fewer casualties.

Now, before anyone gets the wrong idea, I'm not suggesting Jared cheated. Not at all.

He played the game. He understood the rules. And he used the tools available to him to secure a perfectly legitimate victory.

Frankly, I respect a clever strategy.

But there's something to be said for knowing when you've won the battle and lost the war.

And I suspect Jared has had ample opportunity to reflect upon that distinction.

So, congratulations, Jared.

A splendid victory.

A masterful demonstration of diplomacy.

And quite possibly the most expensive longest road ever built.

Not in resources, mind you.

In goodwill.

Now then, fellow adventurers, I want to hear from you.

Have you ever made a move so clever, so utterly devastating, that you were still congratulating yourself long after everyone else had stopped speaking to you?

Because if you have, pull up a chair.

I do love a good story about someone who's far too clever for their own good.