While I agree Ziggler is over regardless of wins and losses so in the long run it doesn't appear to hurt him, however I think in terms of booking this does do a lot of harm to him. If WWE always sees Ziggler as the guy they can job out and keep over, he'll never be treated with any respect, even when they do give him the belt. Does anyone remember the last time he was "world" champion?
No? Yeah because it lasted a minute. If he keeps looking like an asshole I have no faith in what WWE will do with his next reign as champion. I think it's time they start letting Ziggler get aggressive. I think he should get fed up and start a "Rock" type gimmick where he has a massive chip on his shoulder. Perhaps keep the losing streak up a little longer and have him viciously assault his opponents after loses. Eventually start to pick up the "big wins" at PPV events. Establish himself as a cocky aggressive heel before cashing in the briefcase at the Survivor Series.
I'd even say he should publicly dump Vickie Guerrero too and start doing his own mic work. I liked his association with Vickie but I think he'll never evolve into a better character with her around. The next feud I'd like to see Ziggler engaged in with is Mysterio. I think Ziggler's downfall started when he lost a program to that shrimp and it's time he got his groove back by demolishing him at the Hell in a Cell PPV (or whatever is in October). Nothing will make Ziggler a more hated heel that destroying their lovable underdog.
Following that wave of momentum he can ride into Survivor Series with a program against Orton, perhaps a Survivor Series Elimination Match, with his team winning. Before going on to cash in that briefcase, later that evening, to win the World Heavyweight Championship.