OTB Caption Contest Winners

The Captain Jack Edition OTB Caption ContestTM is now over.

The Captain Jack Edition OTB Caption ContestTM is now over.

Couldn’t believe it’s been nearly seven years since the first time I used this picture in a caption contest.


First: J-Dub – Lugar, get up here! I think we’ve finally reached Rino Island!

Second: John Burgess“Just wait until the tax-o-nine-tails bites, then you’ll see who you’re messing with, Matey.”

Third: Robert W. Armijo“♬ I wanna go home. I wanna go home. This is the worst trip I’ve ever been on ♬”


Doug MataconisSail the Seven Seas, they told me. Yo Ho Ho and a bottle of Rum, they told me. Three weeks in and all I do is clean vomit off the deck. This sucks.

Jeremy R – “Do what you want ’cause a pirate is free, you are a pirate!”

Dave Schuler“Arh, she’s sproong a leak”, said the Dread Pirate Roberts.

al-Ameda – “Seamus is strapped to the bow, yes, we’re Toronto bound.”

jfoobar – And this is what results when a pirate’s booty is consistently too high in carbs.

Drew – Look, I understand having to call out politicians shamming taxes as penalties. But wasn’t the court thing supposed to be for life!?


Are you ready kids… who lives in a pineapple under the sea…

As…… You…… Wish……

“Arrrr…. the Pirates Code U.S. Constitution be more like guidelines than actual rules.”

The Thursday Contest is already out to lunch.

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Rodney Dill
About Rodney Dill
Rodney is an IT Implementation Consultant in the Motor City and working within the Automotive Industry. He contributed to OTB from November 2004 until retiring in July 2017, hosting some 1200 OTB Caption Contests.


  1. J-Dub says:

    I’m still waiting on my OTB t-shirt from my first caption contest win.

  2. rodney dill says:

    @J-Dub: Don’t pass out holding your breath.
    …but if we did have a t-shirt, how ’bout this?