In one of the stories in Fr. Groeschel book Travelers Along the Way, he mentions a Sister Mary who quoted something by memory from St. Teresa of Avila. Apparently St. Teresa's brother had been in serious trouble with the law. In desperation the saint prayed: "Dear Lord, if I were You and he were Your brother, I would see to it that he was saved." It would be hard to argue with that.
I also pray for the salvation of various, specific individuals, some of whom may not be that holy, but I love them and have no problem forgiving them. So I reason (and realize) that the Lord is infinitely more merciful than I, and if I am willing to forgive them, certainly he'd be even more willing to do so. Creative pleading?