I'll start off by turning The First heel, twice!
HEEL TURN 1
Militant Gay Rights Activist- First becomes a jerk about things, calls crowds 'bigots'. Pretty much works the crowd to get to chant anti-gay things at him so he can turn around and show them that they are exactly what he says they are. CM Punk in a way where he has a point, but he goes about proving it by being a total scumbag. Would work as a face in states that have legalized gay marriage, unless he could find some other anti-gay event that's happened there so he can play that up for more heat.
HEEL TURN 2
"Soulless" Brian Nadalny- First does something horrible, like say, has an affair with Muse and ruins his marriage, and doing this causes him to believe that The Soul Of The First has left his body. He is now no longer The First. This creates an identity crisis in him that turns him into something of a lunatic. I'd try to stay away from nihilism as that's pretty played out...He could become obsessed with identity, since's lost his...Spending his time constantly asking people "Who are you?" (Which is also a cool Babylon 5 reference!) He seeks to force people to explain why they are they way they are, and it's up to him if he accepts their reasoning.
NOTE: If your character has been around for forever, it's no fair face turning them just because all know olde tymie heels just become faces from the legend/nostalgia pop, so giimme something to work with here. Hell, gimme replies for anything.