Last Look Jack

What really makes a villain? Is it someone that does great evil in this world and wishes to destroy everything in it? Sure, but what about the man that just wants a better life that has to pull himself up from the gutter of the world and fight for every crown. A man who wished he could be honest in life but had to steal that heel of bread to keep fighting on day after day. The man who had to kill or he would be killed.  Is a villain to you just a man trying to take a bit of this world for his own, a man who seeks more in life than to be another man tossed to the King of The Deep?  I will tell you my friends if that makes a villain, then I am the most evil bastard in this world. For I will take from this world because without a doubt I know that this world will take from you if you don't fight for yourself!  These so-called heroes at our door wish to seek us because we fight for ourselves and for our families because no one else will.  So how about we go show them how villains fight! 
-Speech from Jack to his Crew of the Lucky Venture before a sea battle

Well, to start I don't see myself as a villain, or evil for that matter. I am just a man like you, well except your a gnome.  Nothing against your folk you are just no luck on ships. 
I grew up on the barrier islands south of the Jillian coast. Beautiful down there, sun and sand like nowhere else in the world. There is also nowhere better to get rubies the size of your head.  So with that, every trading company and mining company came to strip it dry.  Dear old pa and ma got caught up in the labor and died in those cursed mines.  Left old Jack here to fend for himself. I know it's a tearful tale it be. 
But you see that's where I got my first real lesson in life, that if you want to thrive in this world you can do it two ways. One you can go keep your nose down day by day and hope Ifnia looks down on you and you get lucky enough to scrape by a little home. Or you take what you want and damn others in this world.  I am not saying to harm others just to harm them or take everything from them, do not mistake me.  We take what we need and what we want unless you can stop us, I value strength in body and mind, but that won't save you from my blade if I want your hat. Luck you...your hats to small. 
From the first time, I stole something, a bit of bread for myself. I knew this was the way, I could either work and slave myself out for those corporate bastards or take from them. I slept that night with a full belly and a clear conscience. From that day on I lived by a code, take for yourself and those you care for and damn the world. 
I joined up with a captain on a small fishing boat soon after and left the port, wanted for a bit too many samplings at the market stalls. A few weeks later we were attacked by a pirate vessel, we apparently didn't have enough fish aboard to pay the due so they gave the pirates me as payment. 
That...that was their first mistake, as they were handing me over I grabbed some rope and strangled the dear old captain of that boat.  Then I stepped onto that pirate boat of my own free will. The last thing those bastards saw was me before I torched their ship. I suppose that's how I got my name, Last Look Jack.  Plenty of men and beasts see me as the last thing they see in this world before going to see the King of The Deep.  But I wasn't all bad, I never left a man to drown out at sea, never hit a woman that wasn't trying to stab me.
But what can I say an old pirate like me doesn't last long in this world, we make too many enemies of good folks like the good people here of the Ithlondian Navy and their corporate trading partners.  So you go and write your article about me and how I'm the villain of this world, a horrid man who does only for himself. Now if you excuse me I got a date with the gallows, and a few accounts to settle with my broker from the harbor investments.

Letter of an interview with Torcreek Breadfellow, Journalist for the Ithlonidan Press shortly before his escape. 

The last look is a pirate captain that was plaguing the seas off the coast for twenty years, said to be fair but brutal in his raids, killing all those that fought back but sparing those that laid down arms.  He took what he wanted and considered himself to be a hero of his own story on the seas.