In taverns and whorehouses and theaters across the Taldane Empire, Cayden Cailean is known as the lucky drunk. 

Everyone knows that you become stronger if you face danger. And if you're the kind of person who faces a lot of danger-- if you like taking risks, if you're impulsive, if your wizard friend once gave you a headband of wisdom and when you were like "but I'm not a cleric" said "that is not what this headband is for"--

Well, if you're that sort of person, and you're very very lucky, you can get very strong indeed. 

Cayden Cailean's not very smart but he's not an idiot. He knows he's better at fighting than... pretty much anyone who can't buy a quarter of Absalom with the magic items they have for daily wear. These days, when he says "yes" to an incredible idea that he shouldn't have said "yes" to, not only does he not escape by the skin of his teeth but half the time it's not even hard. He takes down undead single-handedly that any normal adventurer would need a team for. He spent a few years constantly looking over his shoulder because he broke a contract he really shouldn't have broken, and then one day he turned around and stabbed the guy they sent after him and then stabbed the next few guys and that was the end of that. He can piss off anyone he wants, these days, and they can't do shit about it, and Calistria does he abuse this privilege. 

Cayden used to spend a tenth of his time homeless, barely escaping debtor prison with his wits; then at some point he was earning enough as a sellsword that not even he could spend all of it; then he started having to drop off bags of gold at the temples of Shelyn and Arshea and Sarenrae and Calistria and Besmara like some kind of rich Nocticula-fucker buying his way into Axis. He took care of all the kids whose moms he fucked at about the right time, then he had enough to pay a cleric to do a prophecy and track down any kids he missed. 

Cayden's personal record for having a magic item before he gave it away is six months (the headband of wisdom, it was a present so Cayden felt bad about giving it away, and arguably the wisdom was helping). Yeah, he can use the boots of speed to be slightly less likely to die in battle, but that lady can use the boots of speed to escape her abusive husband, which seems way more important and anyway Cayden is already great at not dying. And, you know, Cayden likes new places and new people. Everyone sees him as "Cayden Cailean, the lucky drunk, who got a magic item that one time and gave it away like a dumbass." Only Cayden knows enough to know that if he'd kept all the magic items that crossed his hands then he would be one of those people who could buy a quarter of Absalom.  

The problem is that if people know you're powerful, then you have to be powerful. People will start expecting you to have good judgment and political opinions. You have to talk to rich assholes, like, all the time. Cayden is not about that life. Cayden likes whores and drunks and actors and artists and adventurers and anyone who is cagy about what exactly they were doing before two weeks ago, and while the experience should be lightly seasoned with rich assholes it is only so everyone else can take their money. So what if Cayden fails to tell some of the more boring stories and creatively edits the rest to make it look like he should have died a dozen times? It's storytelling. Maybe when he's retired he'll hire someone to write his memoirs. 

And so one night Cayden is very, very, very drunk and pretending he's only a little tipsy, and he's showing off some of the more absurd tricks he can do, and someone says, impressed, "Man, you should go for the Starstone--"

And Cayden thinks, Shit. Why not? I'm the lucky drunk. I've survived everything else.