Big Heenan fan here, but I thought he was pretty weak in WCW, especially during the NWO run. Do you think it would've been better overall if he stayed a heel commentator / pro-NWO back then instead of being afraid of them?
​Bobby's thing wasn't showing backbone, though.  He was the definitive cowardly heel manager and everyone knew it.  Maybe had the NWO forced a shirt onto him or something, he could have joined them to save his own hide because that would be in character, but I don't see him just up and defying them otherwise.  
Now, someone like Jesse Ventura in the same position would tell them to go fuck themselves and probably get over as a huge babyface in the process.  ​