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I don't think Dupree fit in the locker room. You had gatekeepers like Bradshaw, Benoit, Carder and Bob Holly around to filter people out who couldn't cut it. I've not listened to any of Duprees stuff but hasn't he shit on JBL for years for being a bully? I guess if that's the case people probably didn't respect him for not standing up for himself. Aside from a rare exception like Miz who proved himself that's usually death for a talent no matter how much the office is behind you. If guys are telling producers and agents how much of a bitch Dupree is there's no way he would have got far. Vince especially can't accept people who are like that.
Masters I think had issues with drugs. When the Benoit shit happened and a ton of guys got suspended around that time (the pharmacy scandal?) Masters was one of em. As soon as he cam back he was half the size he was previously so the Masterpiece gimmick was practically done for. Also his Masterlock stuff was over but as soon as Lashley broke the streak his entire deal was finished pretty much. He didn't have much talent outside of the gimmick and finishing move so better he be let go and improve elsewhere than stagnate not improving when there's dozens of guys his age but better.