longterm Anomalous and fortunate regression

Our world may seem like it is rigid and unchangeable once time has past but such a view can be broken for the few pitied by higher forces. This has happened in our current era, two seemingly disconnected individuals were given the opportunity to change themselves and the world around them after quite unfortunate and tragic events. One a man broken by his latent ambition, unable to capitalize now and too dire a situation claw himself out of. He is given the opportunity to change that with all that he knows now and the ambition he finally grasps though with a chance to use that ambition now. The other person in this odd equation...well that is a case that is to be written by the other player on this chessboard

(I realized that there are very few ideas made for mutual GMing and actually interesting plots that allow it, beyond that a classic regression plot is always a slippery but fun slope to play with if done right plus it can quickly turn into a normal 1 to 1 rp instead of gming)