The turning point in his life came when his father took on a counselor who turned out to be a wizard with evil designs. The mage planned to murder the family using a summoned demon and then appropriate the title and lands for himself by appearing to "slay" the demon. After murdering the patriarch and the heir, he moved on to the rest of the family. Though with little skill in battle, Alessandro managed to evade the demon and lure him away from the other children in the family long enough for some of the guards to arrive and combat the foul creature. In the process, the evil wizard was found to be responsible and fled. Alessandro, now recognizing the uselessness of his previous lifestyle and consumed with grief over never having an opportunity to make his father proud, vowed revenge on the mage responsible. He turned over his new role as family leader to his younger brother and set out to find the wizard.

Now referring to himself simply as "Alex", he picked up some small skill in tracking but was unable to find his quarry. He wound up in a large city, having lost the trail. He picked up several useful skills in scouting and decided that, if he ever was able to find the wizard, stealth was going to be of better use in exacting his revenge than brute force. Since then, he has consistently attempted to hone his more roguish skills. The irony of his return to the seedier side of life is not lost on him, but he tries to look at it pragmatically and justify his means with ends that he deems noble, hoping that such ends, at least, would have made his father proud.