William J. Feathersmith

William J. Feathersmith is the protagonist villain of the Season 4 episode of The Twilight Zone, "Of Late I think of Cliffordville". He is a sadistic robber-baron of a businessman who has made his career off of using, abusing, and then discarding others when they are no longer useful. However, by the time we see him, he has grown bored due to feeling he has nothing left to do, and so makes a deal with the Devil to go back in time to the town Cliffordville as it was in his youth.

History
Mr. Feathersmith is first introduced to the audience having a meeting with an old associate of his, Mr. Dietrich. He offers him a cigar as an ostensible show of politeness, but Dietrich declines. It then is made clear to the audience that Feathersmith and Dietrich have a long, sordid history with one another, with Dietrich describing Feathersmith as a thoroughly ruthless, immoral man who preys upon others. This assessment is in fact true, as Feathersmith then gleefully reveals that he bought a note for three million dollars that Dietrich owes, and demands that Dietrich pay him the full three million dollars immediately. Dietrich weakly protests, pointing out that, if Feathersmith calls the note, he shall be bankrupted and lose everything. But, Feathersmith calls the note off-screen, ruining Dietrich. Mr. Feathersmith laughs gleefully as a crushed Dietrich leaves his office.

However, when next we see Mr. Feathersmith, he has become quite drunk and it becomes clear that he is now bored and feeling lost and directionless in life due to having succeeded too much; in his own words he has "gotten everything there is to get" and no longer feels he has anything left to aspire to. Shortly after, he meets a female Devil, who offers to give him what he wants: the chance to go back to a town called Cliffordville, where he had spent his youth and had his start as a bussinessman. Nostalgic for the town as he remembered it and wishing to go back and claim his success all over again, Feathersmith agrees to make a deal with "Miss Develin". He offers her his soul, but she points out that, after all the wicked deeds he's done throughout his life, his soul is damned to Hell and is not his to offer. Instead, she demands that he liquidate his fortune and give the better part of it to her. He reluctantly does so, and is seemingly de-aged to a young form and sent back to Cliffordville.

At first excited, Feathersmith is horrified to discover that he cannot capitalize on the investments he had been hoping to make due to various complications, is repulsed by unpleasant things about the past he had chosen to forget about or remember differently, and finally realizing that, though Miss Develin de-aged him outwardly, his biology is still that of an old man, and so he will not live long enough to see his investments (such as they are), come to completion. Running into Miss Develin, she needles him for having built his whole career on using and hurting other people whilst creating nothing worthwhile himself. He begs Miss Develin to take him back to the present, which she agrees to do...if he can afford the train ticket. Feathersmith sells the last thing he has of value and buys the train ticket, leaving Cliffordville and returning to the present in disgrace.

It is then revealed though, that because of all the things he did in the past, Feathersmith does not go back to the present he had left for Cliffordville, but instead a new timeline informed by his mistakes in Cliffordville. Among other things, he has now been reduced to a lowly janitor.