Contract killers don't usually have families because all that "leaving the wife and kids out of things" stuff is fiction. It's impractical to have a family, first of all, but at some point the family is going to be threatened or worse. If a boss wants to exclusively control someone who kills people for a living, he needs to find a weakness to exploit - a woman, a child, a parent, even a pet, or a prized possession. If the hitter has no weaknesses, he has all the power and you're not his boss, you're a client. DeMeo liked to be the boss, the didn't do the "client" thing. Kuklinski knew that his wife and kids were fair game, but he figured he was so dangerous that nobody would ever make a move against them. He didn't understand that from the day he said, "I have a wife" and took DeMeo's money, DeMeo literally owned him. He also didn't realize that he wasn't a hit man, he was a pool shark and a budding serial killer who liked to hustle and kill...it didn't being about money after he got married, and by then he'd killed a lot of people over real or imagined insults. DeMeo would keep a dog like that on a very short leash and threaten the bitch and puppies every chance he got.
So now Kuklinski and Mister Softee are in the same boat, both in hot water and both with vulnerable families. Neither of them wants to kill his own. By killing each other's family, they can take power into their own hands and maybe disappear. They're not going to be partners anymore anyway (a partner being the second-dumbest thing you can have after a family), and this way neither can rat on the other. On the surface, it seems like a rather elegant idea. If they can can put a "humane" sort of spin on it by choosing to believe that it will spare the family future suffering, so much the better.
The only problem with it is that "You won't even wake up" has more than one meaning, and by then Kuklinski already knows that Mister Softee is going to try to kill him.
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