He is the Underdog in eveyr match, doesnt work for a heel.
He would need to start a group or get a bodyguard that could help him.
Start a run where he is heel and continues to slide through wins by cheating and interference or stipulations.
He could never be a dominat heel, but could be the Cowardly cheater heel.
Have him get sick of playing hero for the kiddies and getting beat up for doing what is right. Have him "hold out" of matchers for more money.
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