Damn...
- When Vito finds out that his mother has died - while he's in prison, no less. He has just sent his sister off to collect his money and buy her the best doctor money can buy. She died while Frankie was visiting him in prison, possibly of a broken heart.Vito: No, no no no - Fuck!
- Marty's death - especially Joe's reaction. Joe just wanted to teach the kid the ropes and gave him the least dangerous as well as safest role in the heist. It was just bad luck that Clemente escaped the same way they were going to.
- Henry dying horribly at the hands of the Chinese. The Triad attack him with meat cleavers in the middle of Central Park in broad daylight. They give him a Death of a Thousand Cuts then leave him to bleed out. He's implied to be still aware of what's going on when Joe and Vito arrive too. They were minutes too late.
- The pause screen music.
- For veterans of the first game, discovering Vito and Joe are Tommy Angelo's killers is a massive kick in the teeth.
- Even worse, the two have no real idea of who Tommy was or why he turned on the Salieri family. They don't care either; they just need money ASAP, and killing him is a good way to do it.
- Vito's Heel Realization speech in Chapter 15Vito: This wasn't how I imagined it when we were startin' out. I dreamed o' money, cars, women, respect, freedom... I guess I ended up gettin' all of that more or less, but along with it came prison, living in constant fear, and the blood of my friends. I ducked it as long as I could, but it was finally catching up to me. It was all just a matter of time...
- The ending is this one, Vito and Joe have managed to kill Falcone Family, ending all tensions between Empire Bay Crime family and Triads. It's seems like Vito and Joe are now free and can go back to their ordinary routines, right? Except, it doesn't work that way, as somebody has to take the fall for the massacre they did to the Triads on their territory. Vito learns this the hard way, as he watches Joe being carted off to be killed as a price for it, unable to do anything about it.Vito: (watches Joe getting taken away) Hey, hey! What the hell's going on? Where are they taking Joe?Leo: Sorry, kid. Joe wasn't part of our deal.
- Vito's face after hearing Leo's response, he's angered with himself that the whole deal with Leo was All for Nothing. He has lost everything, his violent criminal life turned his family and friends away and now he has unwittingly sent Joe, his only best friend, to his death. It's no wonder why he acts so bitter in the third game.
