Dolph is an objectively fantastic in ring worker, but his skill set offers nothing that WWE doesn't have covered already. He's kind of established and can even be thrown into Main event matches and shine on a given so it isn't that he's not valuable. It does kind of suck, because there are these guys like him that are going to be put on the back burner for other priorities. So not only are they talented and don't have a single opportunity to show it on regular, but also are walking on thin and have to deliver on the notice they get one.
It probably is better to stay in WWE than it is to jump to anywhere else. Cody Rhodes is somewhat of an exception, but all the other guys that either requested release or got cut flounder due to the talent gap. The upper echelon of the European and North American independent scene really do rule and it's even harder to work in a place like Mexico or Japan. I think in most cases it's be better to be a Dolph Ziggler or even a Bo Dallas /Curt Hawkins to be honest than a Jack Swagger or Ryback. I could imagine the frustration he has and the fact he's being overshadowed weekly doesn't help much.
People like to paint him incredibly negative, but I don't see a lot wrong with his career. Some things went wrong and he isn't exactly the greatest on the Mic. I do think he's improved a lot over the years, but he does really cut the same promo on repeat. I think he'll be remembered fondly in retrospect if he ended up quitting tomorrow and just becoming a stand up comedian. I guess we'll wait and see if he ever gets that one last shot and capitalizes on it or completely flounders until his career ends. I would love to see Ziggler rise to prominence in any role really, but at this point I don't think it's going to come. Frustration is a word that could be used to describe his career on both ends of things for sure.
Ultimately, he's a cautionary tale against the way WWE has done its pushing since the 90's with the conveyor system. I've mentioned it a lot in the past but to remind it is..
Be either a Tag or Low Card star - win IC or US title - MUST win World title within 2 years or be considered a failure - Pushed to title too quickly/artificially - Run Bombs/Get Hurt - Never Recover - Released or Job Forever - Next In Line Moves Up...
If we're being truthful, this guy NEVER had any business near a World title and in the old WWF days, wouldn't have been. He'd have been an IC level wrestler for some of his career, but the majority he would be in a Tito Santana/Rick Martel style role, on the shows, winning occasionally but mainly there to make others look good.
Once Bret and Shawn moved up, suddenly EVERYONE had to...almost according to their template and it led to this kind of situation for guys like Ziggler.
The frustrating (and still unforgivable) part is that it was at the expense of others... Wade Barrett would have had a much different (and arguably more successful) run on top had Zig not hurt him with his "ragdoll" antics, he made a conscious effort to try to "look" like he hit his head on the barrier, to the point he nearly did and Barrett had to take the hit to save him... snapping his elbow in the process. That it happened a second time to Barrett was tragic, but that first one is a big asterisk next to Zig's push... Injure someone and directly beneft? hmmm not cool.
Zig then got hurt himself repeatedly, again arguably due to his ragdoll style to the point he was told to tone it down repeatedly.
There was also the controversy a few years back when he "signed on" for a Max Landis film without permission (he never ended up in it) which ruffled Vince's feathers... sure be in a movie, but do it through the office, not "on your own".
All that is because the pressure was on to hit the main event within that 2 years and to be fair... he did it, but it was an abortion of a run and actually all those efforts left him worse off than had he not done it been released for the movie and come back for another go. Add to that the issues his brother helped cause in NXT and you have a pretty mixed run in the company.
If you look coldly, a lot of people have had World titles in the last few years who never had ANY business with them... and Ziggler is perhaps the most glaring example, it's easy to say Cesaro or Nakamura deserves it and Jinder doesn't.. but they are also potential Zigglers... Some like Cody read the writing on the wall and balked and now that seems to be what Dolph is doing.
No loss... literally none. There are already 5 people in NXT or on the roster who DO have business near a title who've yet to have a "proper" WWE World/Universal title... Roode, Joe, McIntyre, Strowman and Matt Hardy all have better claims to get the push than Ziggler now.
He's more Shane (Dean) Douglas than HBK career wise... so much potential, but had to do it his way.