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They've always used each other for their own reasons. They both know it, too, even if the reasons aren't readily apparent. In Droog's case, some of those reasons aren't apparent for a very long time. Jack knows he's a cunning bastard, but he's unable to let him go. Boxcars and Deuce don't see the way they use each other, only the way they stick together. The idiots have mistaken it for some twisted sort of love.
Boxcars especially. God, Jack hates his insistence seeing the two of them kissing each other. Droog always responds by soundly beating Boxcars with his cuestick. Jack just yells at him to shut up.
What Jack doesn't want to admit is that maybe, for once, he'd like to use Droog in a completely different way. Drop all the pretense, all the planning bullshit. And maybe give in to Boxcar's suggestion. When the giant oaf is nowhere around to brag about it, of course.
If only that could happen. But it probably never will.