LogFAQs > #878273413

It's not anywhere near the cruelest, but Mafia 2:



The main character Vito and his best buddy Joe get into some heavy shit, but you're given a deal by the mafia commission to get out of it by killing the main antagonist.

After you do it, the other mafia guys say they're going to take you both out to go celebrate, but Vito and Joe are taken in separate cars. You then see the car Joe is in turn in a different direction You're then told the deal only was for you and Joe, who is a pretty funny and likeable character, is taken away to be killed.

Not cruel like other endings here, but it did kinda bum me out. Nice twist though and it's realistic.
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http://i.imgur.com/hslUvRN.jpg
When I sin I sin real good.