I'm a broken man on a Halifax pier

As part of my pledge to deliever new, albeit likely unwinnable, cases, I'd like to present a case I thought of for use at the Dal mini tournament but ended up not using in favour of an equally stupid but (I thought) more winnable case about Kevin Federline. Ms. Bond informs me this case is similar to one run previously involving pirates becoming privateers, but this one is a little different. This one has a song.
http://www.jsward.com/shanty/barrett.html
BIRT: The year is 1778 and you should join Captain Elcid Barrett, and become a privateer on my ship the Antelope. There are five reasons why you should do so.
1. Duty to King and Country - We are at war with the rebelious American colonies, it is duty of every citizen of the British Empire to help put down this rebel scum. Captain Barrett has a letter of Marquing from the King himself and you know this is a totally legitamate operation. 2. Money - So you're a young man in Nova Scotia? Your career options are basically become a fisherman and hope you catch enough fish to not starve OR become a farmer and hope you grow enough crops to not starve. American ships are loaded with money and goods going to France and Spain for trade and are coming back with valuable weapons and European goods. Either way valuable stuff that will both help disrupt the American's war effort and when the voyage is over you get a cut of the money we make, which is far more than you can expect to make otherwise. 3. Easy Money! - The Americans have no powerful naval Ships of the Line. Not one! We would only ever have to deal with merchant ships loaded with plunderables. Not to mention we are British and have a proud sailing tradition, whereas they are riff-raff without a navy. We can easily out sail them. The American rebels hardly ever stand and fight on land, they attack us from the woods like cowards or Indians. Those fearful tactics won't work in the open ocean where there is no where to hide. These guys are so weak they will probably surrender at the sight of us. I doubt we'll even have to fire our guns. 4. Travel oppertunities - We will be going all up and down the coast of North America and to the Caribean. People in this day usually spend 98% of their life within 10 miles of where they were born. The mere fact that you, sir, have come all the way to Halifax from Sherbrooke tells me that you are a man of adventure. How else would you ever see Jamaica? White sandy beaches, clear blue water, palm trees. You ever see a palm tree? They are not to be missed. And it's warm! No more fog and dank weather in the middle of summer. 5. Ladies - Women love a sailor, and women love a guy who is financially secure. You will easily make enough money on this trip to settle down and find a wife. Or if that's not your thing you will easily have enough money to hire all the whores you could want in Port Royale. It's win-win.
Clearly, anyone familiar with the song knows that Barrett is a terrible captain and his ship is a (barely) floating piece of garbage. So to have an effective clash it would be best to run this case against a team that is likely to know the song. Here is the order of preference from best to worst: Capers, Bluenosers, Maritimers, Newfies, other drunken teams, other Canadians, Americans, Albertans. The obvious counter argument is that Barrett and the Antelope are worthless and that the dangers of the privateering life outweigh the supposed benefits, so be prepared for this. I feel that this case has potential, but I've clearly been wrong about these sorts of things before.