When "The Wreck" main mission is active, head to Darunda Diner in Jaunta's Hope.
There at the bar will be a criminal drowning his sorrows (if you're having trouble finding him, he's next to Verrick). Talk to him and I believe it doesn't matter which option you choose but for reference I chose to 'pry' his story out of him and after the criminal goes back to his bottle, the trophy pops.