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I was actually a fan of the Henry v Show feud concept, I thought Henry would continue his run and squash show. But that feud definitely deserves a place after Show buried him like 4 PPV's in a row.
Jomo had potential imo, he did get over at times but they always buggered his push up. He would have been a great uppermidcarder for me. Jeff drew but always has the stigma of where is his next fuck up coming from.
Jeff's WWE and WHC reigns were short as hell. So him going over Punk wasn't that bad of an idea.
Punk wasn't in the business for too long back then, so it would be possible.
Punk debuted in 2000 so had been in the business for just as long as Jeff and in the WWE for 3 years, proving himself as a major heel. Jeff's contract was up and he made no intention of renewing, so why put him over?