The Unluckiest Pirate Ever

Bartolomeo was a pirate. Or tried to be.

But he was a VERY bad pirate.

Not bad, like mean. Bad, like… nothing he tried ever worked.

One time — by pure chance — he finally caught a treasure ship — a BIG one, full of gold!

“SHIVER ME TIMBERS!” he hollered. (When pirates get excited, they yell stuff to impress other pirates. Older, well-seasoned pirates often resort to simply muttering, “Arrr!”)

Bartolomeo did a happy dance right there on the deck. He even tried a cartwheel.

He probably shouldn’t have tried a cartwheel.

When he got to his feet, he spied three giant ships. (Pirates never see things. They spy stuff.) Coming right at him.

“Blimey,” said Bartolomeo.

“ARRR, YE BE CAPTURED, YE SCALLYWAG!” yelled the Spanish captain.

“Aye,” said Bartolomeo glumly. “Aye, I be about to be, I be.”

The captains of the three Spanish ships locked him in a dark, smelly cell way down at the bottom of the boat. It smelled like old fish, wet boots, and someone’s regurgitated lunch.

Bartolomeo sat in the dark.

He was very, very sad.

I always mess up, he thought. Nothing ever goes right for me. Nothing. Ever. I am the unluckiest pirate to ever sail the seven seas. I am probably the unluckiest PERSON to ever sail the seven seas. I am possibly the unluckiest person to ever do ANYTHING.

Pirate Pause:

Have you ever felt like Bartolomeo? Like you just can’t do ANYTHING right?

You don’t have to answer. I’m only a tall sea tale. I can’t respond.

End of Pirate Pause.

Right then, Bartolomeo looked around his smelly cell.

There were some big clay jars in the corner. The round, wobbly kind. The kind that float when filled with air, not water, and corked tight — which these were.

Hmmmm.

That night, he grabbed those jars. He pushed one, then another, through a tiny little window in the side of the boat. Now, Bartolomeo was not a tiny little man. It took a while. It was not graceful. And with a sleeping crew nearby who snored loudly (pirates snore louder than landlubbers), it took a bit for Bartolomeo to squeeze through the hole. But desperate times call for dispirited treasures, and Bartolomeo, using shards from a busted grog mug, cut the hull’s planks to make the hole bigger and…

SPLASH! He tumbled into the cold, dark ocean.

He hugged those corked clay jars as tight as he could.

And he kicked.

And kicked.

And kicked and kicked and kicked.

Then he stopped.

“BLIMEY, these waves be cold!” he sputtered. “It’s a long way to shore. And the water is deep. And I —”

A shark swam past.

Bartolomeo passed out.

At some point that night, he washed up on a beach.

He flopped down face-first in the sand, soaking wet, with no treasure, no ship, and no shoes. A little crab walked up and stared at him.

“Arrr,” said Bartolomeo.

Click, click, said the crab with its claws.

“En garde!” yelled Bartolomeo, striking a sword-fighting duel pose.

The crab scampered into a hole.

Then Bartolomeo laughed. A big, soggy, sand-in-his-beard laugh.

Because even the unluckiest pirate in the whole entire world… was still ALIVE. And as long as he was alive, there was always hope that another treasure might one day find its way into his lap.

Stick to the Code

God didn’t give Bartolomeo a magic boat. He didn’t make the bad guys go away.

But right there in that smelly cell, there were some silly little jars.

Just enough to help him escape and live to hope for another day.

God is really good at giving us hope. When things go all wrong and you feel like giving up, He leaves you just enough of Him to look up, look out, and look past where you are. Maybe it’s a hug from your mom. Maybe it’s a funny joke from your friend. Maybe it’s one little brave idea in the dark.

You just have to look for the jars — that glimmer of hope.

“I can do all things through Christ who gives me strength.” — Philippians 4:13

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Let’s Talk About It:

• Have you ever had a day when EVERYTHING went wrong? What happened?
• What’s one little thing God gave you to hold on to?
• Can you think of someone having a hard week? What could YOU be their “jar”?

Remember: Even on your worst day, God leaves you something to hold on to. Look for your jars! 🪣

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Sundays, you’ll find the Pirate Preacher in Moore Square, Raleigh, NC, and at the bus station. There, Team Jesus passes out food, water, chips, and cookies. We also lay hands on and pray with other so they may enjoy the abundant life Jesus promised (John 10:10). His books are read by countless inmates and used to introduce others to Christ. 

The Pirate Preacher is an award-winning author of middle-grade, YA, and adult fiction who loves to surf. Send a message in a bottle to the Pirate Preacher: PiratePreacher.org@gmail.com