Here are my thoughts on how I see Henry winning the WWE title, if he ever wins it.
I think that he will lose at Money In The Bank. Then Cena will lose at Summer Slam to Bryan. And Bryan will lose to Henry at Night Of Champions. Finally, Henry will lose to Bryan at Hell In A Cell. From this, Henry challenges Bryan on Raw in a rematch, but loses. Henry cries foul... Controversy. Whoever is the World Heavyweight title holder comes out to confront him. Consequently, this exchange leads to a match at Survivor Series. Henry wins his second World Heavyweight title. At Royal Rumble, he defends his title but, eventually, loses it to Barrett on Raw. At this point, I would give Henry a shot at the tag team titles with Langston or other. It doesn't necessarily have to be a long run. The point is to have Henry conclude his career on a positive note and for him to pass the torch to Langston to be the next powerhouse heel. Eventually, I think he [Langston] will turn face and be that for a while.
I chose Night Of Champions since Henry has won the ECW and World Heavyweight titles at the same PPV.