Mission outline?

I was thinking on how my mission should work, and I had few ideas. I would lie it structured like this. 2 fight, against the same guard, within few years of distance in-between.
First day of prison, you argue with him and during the night (so I don't have to create all the prison inmates but I can fake them) I fight with him, winning but getting tazered and ending up in isolation, or something fancier like "the hole" or some bullshit like that.
Second, I'm in my cell and the boos of the prison request my presence and he tell me that the same guard (vinnie?) has gone too far and that he need to be killed. Escape from the window, find him in a room after I jump around on the roofs (an hidden part) and I kill him, first I beat him, then I shoot at him.
Sounds cool, but think it its one thing, make it its another.
In the meanwhile here it is a fast sketch of the main character meeting with the boss(italian mobster stereotype).