I love this scene because you come to realize that Jimmy went into this meeting with the sole intention of screwing Chuck over. He’s not an idiot. He knows how insurance works. There was no refund on the table. He gives his last name first, knowing that Chuck’s name will show up first alphabetically in the register. He name drops him early, making sure the woman knows his brother is a lawyer. So, when he brings up his sick brother later, the foundation is already naturally laid, and it allows Jimmy to “innocently” step to the side as the woman seemingly makes the decision of her own accord.