OTB Caption Contest

Time for the Thursday OTB Caption ContestTM

Time for the Thursday OTB Caption ContestTM



Winners will be announced after Tuesday PM.

FILED UNDER: Uncategorized, ,
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. Michael J. Listner says:

    The job market is so lousy that I really need to start interviewing for a new job after my term is up.

  2. markm says:

    Pirate: “……so…..the International Brotherhood of Ship Looters (IBSL local 413) on good faith will refrain from pilfering cargo vessels and in return……..we get all the land West of the Mississippi and a four year exemption from ObamaCare for our Cadillac healthcare plan. DEAL!”

  3. rodney dill says:

    Obama: “Do you really need to open carry in a Starbucks?”
    Pirate: (shrugs) “Pirate…”

  4. JKB says:

    Putin isn’t so tough. Even a man in a pirate costume dominated Obama.

  5. JKB says:

    Quick, which one looks more Presidential?

  6. markm says:

    Pirate: “Sponge Bob has a list of demands……..”

  7. markm says:

    Pirate: “…seriously…it’s tough out there and things don’t seem to be getting any better. Can you pivot just one more time to the economy????”

  8. Mu says:

    Pirate: “Come on, it’s Halloween, what are you dressed as, President?”

  9. John Burgess says:

    “Dude! I didn’t realize Somali pirates dressed so much better than Indonesian pirates!”

  10. C. Clavin says:

    Obama: Seriously…there’s this guy…JKB…he’s even sillier than you are.

  11. Tony W says:

    The RIAA finds a new, creative way to make their case directly to the president.

  12. Moosebreath says:

    Ted Cruz discusses raising the debt ceiling with President Obama.

  13. Franklin says:

    Peace talks between neighbors Somalia and Kenya.

  14. JWH says:

    As the end of his second term approached, President Obama, like previous incumbents, sought an achievement that could be his legacy. With Middle East diplomacy a difficult, if not impossible, endeavor, President turned his thoughts to a more attainable goal: resolving a longstanding feud between pirates Edward Teach and Stede Bonnet. Here, the president meets Daniel Bollegren, whom the president appointed his special envoy to the pirate captains. Mr. Bollegren conducted extensive research into piracy so that he would be better able to relate to Captains Teach and Bonnet in initial discussions. Unfortunately, due to sequestration, Mr. Bollegren’s research budget included only enough money to rent the Pirates of the Caribbean movies.

  15. Beth Lopez says:

    What do you mean you won’t be my Defense Secretary?!

  16. Which party is he from? He’s an ARRRRRRRR, of course.

  17. rodney dill says:

    Obama: “No, seriously, The U.S. doesn’t recognize ‘International Talk Like a Pirate Day,’ by talking like pirates at the White House.
    Pirate: “What about that elderly balding white-haired guy outside the hatch. He was blowin’ me down with some drunkin’ pirate trask talk, me hearty.”
    Obama: “That’s just Joe Biden, he always talks like that.”

  18. Unable to get congressional backing for an attack on Syria, Obama was forced to resolve the measure by signing Letters of the Marque for the first time since 1815.

  19. Anderson says:

    “So it’s this Assad that ye’re wantin’ to take a long walk on a short pier, is what ye be sayin’ ….”

  20. Maggiemama says:

    Obama: ” So then Secretary of State Kerry made a terrible political gaff …”

    Capt Hook: ” Trust me, Mr. President, I really know how to handle a gaff.”

  21. JWH says:

    @Stormy Dragon: I love your caption +a zillion for the historical and constitutional reference.

  22. Pharoah Narim says:

    “Let me get this straight…you’re here from Bethesda to do my Prostate exam?!?!?!?”

  23. “That be all well and good, Mister President, but unless ye be giving me a waiver, I be having to cut Polly’s share of the booty to only 20 hours per week.”

  24. JWH says:

    President Obama dashed all hopes for diplomacy when he informed Captain Naif that his parrot wasn’t real.

  25. rodney dill says:

    @JWH: That’s funny. It blends in so well with his hat and coat I hadn’t even noticed the parrot.

  26. JWH says:

    “Those ‘Lost Boys’ are nothing but terrorists!! I request that the Unites States send drones!”

  27. JWH says:

    Donning a cunning disguise, Dominique Strauss-Kan sneaked back into the United States, only to be arrested for “aggravated pirating.”

  28. rodney dill says:

    Shark attack? No. I once reached for a cupcake the same time as Chris Christie did.

  29. JWH says:

    House Republicans wanted an arm and a leg to raise the debt limit. Fortunately, the White House negotiated them down to a hand.

  30. al-Ameda says:

    Trying to reason with Eric Cantor is difficult.

  31. Franklin says:

    “Believe me, Mr. Hook, I already know what Neverland is like – it’s called Congress.”

  32. LightsOut says:

    Obama: “Does Polly like crackers?”

    Conservative Pirate: “You be the most racially divisive president evarrrrrrr!!!”

  33. Michael Hamm says:

    Hand reattachment surgery under Obamacare is limited to one “digit” only.

  34. AnnS says:

    obama: “I just want to apologize to you for the Barbary Wars.”

  35. Neil Hudelson says:

    …and so then I told Hank Paulson that we would need the government to bail us out, and while this was happening, we were telling homeowners that…”

  36. CSK says:

    “Of course I’m a real pirate, Mr. President. Would I Kidd about a thing like that?”

  37. JWH says:

    @CSK: Grrrrooooooaaaann.

  38. CSK says:

    “Why yes, Mr. President, I’d be happy to Teach you the ins and outs of piracy.”

    @JWH: Just for you. 😀

  39. JWH says:


    President Obama looks for somebody to attend state dinners in his Stede.

    Pete Townshend visits the president to assure him the Kidds are Alright. Or all left, by this picture.

  40. CSK says:


    “I gotta tell ya, Mr. President, the ladies LOVE this Blackbeard of mine.”

  41. Pinky says:

    “See, now, ‘first mate’ has always confused me, because it’s like a vice-president, but it sounds like a first lady.”

    “Arrrr. If the voyage is long enough, that’s a distinction without a difference, sir.”

  42. jd says:

    I’ve gained the whip hand, Mr. President… my invisible bomb beats your invisible grapnel!

  43. Parrot: “where da cracka?”

  44. Tony W says:

    Seeing no future in his own party, Speaker Boehner (in disguise) makes his case to the President to be named Secretary of the Navy.

  45. JWH says:

    “Unlike you, Mr. President, I have no term limits. That’s why ..

    ‘Tis a wonderful thing
    ‘Tis a glorious thing
    To be a Pirate King!”

  46. JWH says:

    During the Clinton years, a “pirate’s booty call” meant something else entirely.

  47. JM says:

    “So, no one takes you seriously either?”

  48. He who must not be named says:

    Well, Mr. President, I reached out and touched a pirate like that. Once.

  49. He who must not be named says:

    You will always remember today as the day Jack Lew almost balanced the budget.

  50. He who must not be named says:

    Aye Mr. President, personalized ethnic Internet marketing is frought with problems, we call it the curse of the black PURL.

  51. He who must not be named says:

    No, really, I’m not Johnny Depp. I get that all the time.

  52. He who must not be named says:

    As a seaman, I’m not impressed.

  53. He who must not be named says:

    “Do you know I got bin Laden?”

  54. He who must not be named says:

    The buccaneer stops here.

  55. He who must not be named says:

    “Well, if you have more than fifty full time crew members, on October 1 you are required to provide them each with a DHS approved health care option or face a substantial fine.”

  56. Tillman says:

    “Pardon, I thought I were in the United States, not the Dominican.”
    “No, I’m the President.”
    “…really? That be a stretch. I need to be seein’ yer birth certificate.”

  57. He who must not be named says:

    A three hour tour…

  58. He who must not be named says:

    The pirate and the privateer.

  59. He who must not be named says:

    President: “I like the cut of your jab.”
    Iron Pyrite: “It’s jib, sir.”
    President: “I like the jib of your jab.”

  60. Lounsbury says:

    Pirate: “We on the Board of the Council of Honourable Free Libetarian Captains are conflicted you see, Your Excellency, about this vexed question of insurance. On one hand we don’t much like mandatory fees and coverage you see, being for free contract. On the other hand, so many us do lack the other hand – pre existing condition we’re told, and it makes our normal rates for coverage right intolerable. Perhaps you can look at how we Poole our treasure…”
    President: “And you can work the other side?”

  61. “You know with my Obama Care becoming active in a few months. Soon you can have your leg removed and fitted with a wooden peg.”

  62. “I should’ve known better than to rub my eye. But you see I wasn’t use to the hook yet.”

  63. “You can do so much pillaging, plundering and raping. After awhile, it gets old. So I decided to switch careers. Now I’m a hedge fund trader down on Wall Street.”

  64. “Aye…Ay, ay, ay, ay my eye hurts.”

  65. ♫We’ll be the Pirate Twins again, Europa…Ta republique♫

  66. President Obama pleads both with Wall Street’s chief hedge fund trader and its foreign sovereign investment fund representative to stop the plundering, pillaging and raping of America’s assets – just kidding.

  67. “Aye, I speak for all the hedge fund traders. You’ll get your shanghaied Captains of Industry back, just as soon as we get our ransom: The Forfeiture of The American Citizen’s Right to Vote”

  68. He who must not be named says:

    Well sir, someone saw your Captain Morgan impression last week and decided that they better send me in.

  69. He who must not be named says:

    Well sir, someone saw your Captain Morgan impression in last week’s caption contest and decided that they better send me in. Oh, and thing you asked me for, you know the thing with Biden, it’s being taken care of in the next caption contest.

  70. He who must not be named says:

    That’s strange, President Obama usually relies upon major media figures to parrot his talking points.