I interpret it as something like this...
It could be that he is logical in that respect. He understands the value of having trusted allies and the concept of loyalty, it could be a transactional and honest arrangement. Many hands make light work. But as stated, he is a "cold bastard", which means he might lack empathy for others, hence appearing very cold or insensitive to peoples emotions and responses to things he does. He might also have a gloomy or dark personality too, think of alt-scene like a goth (he kind of looks like one too!).
His smile could be very practiced, like a CEO warmly greeting you with their crap-eating grin, it is used to put you at ease, but the smile doesn't quite touch his eyes, as it were. Nice is the behaviour of acting polite or respectful, which he can be, but he is not a kind person.