Teammates always talked about Stockton's leadership, humor, will to win, passion, knowledge, etc. He does not have an outgoing personality, but neither does Sloan. I heard Dan Patrick talking about Game 6 of one of the NBA Finals and he said that he was standing at the Jazz locker room when the team was headed in right after the defeat. He heard Stockton's son say to him, "Those refs robbed us." Stockton stopped and took his son aside. He said, "We don't make excuses, ever." Dan Patrick said he was blown away that Stockton could turn such an emotional letdown into such a powerful teaching moment for his son. He said he will always have mad respect for Stockton, and that he knows of many other national broadcasters who feel the same way. He said that Stockton never was particularly friendly to him, but he will always wish him the best in everything he does.
Do I think Stockton would be the best with the media? No, but I think they would respect him. I think his strengths would be in leadership, intensity, competitiveness, etc. It's likely that we'll never know, though, because I doubt Stockton takes that sort of a job even if it's offered to him. It would be so damn cool if he did, though.