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Steinbeck's first description of Dakin is designed to make us not like this guy. He has "veiled eyes" and an "immobile mouth." He and his wife live in obvious comfort compared to the other working men, with folding cots for their children and really awesome dental work between the two of them. And then there's the dude's pride and joy: a shiny, new truck.
Dakin tells Mac and London straight up that he's not a man of ideology or risk:
"... get this straight. I ain't doin' no time for no kind of outfit. If you belong to anythin', I don't want to know about it. I got a wife and kids and a truck. I ain't doin' no stretch because my name's on somebody's books." (63)
So, basically, dude's all about the coin and what's best for his bottom line. We're not about to blame a guy for wanting to get ahead, but Steinbeck clearly draws Dakin in stark contrast to protagonists—and idealists—Jim and Mac.
Dakin's desire for personal gain is not seen as an attractive quality. He has pride in his things—including his wife and kids—because they are nice possessions. This self-interest translates into a character with kind of coldness about him that Mac notices not just in his demeanor, but also in his way of living:
"He had no vices; every cent he or his wife made went to his living, to his truck, to providing new equipment for his camp." (108)
It's a peculiarity that sets Mac's teeth on edge (he also notices this about Jim, too), particularly because Dakin is the sort of man to put himself on a higher plain than the other workers. It isn't long before he and Mac lock horns.
When the men head to the train station to intercept the scabs and then witness Joy's assassination, it's London who takes the lead. Dakin is horrified by Mac's decision to take custody of the body to show it around camp, to perk up the men. He doesn't understand the finer points of manipula—erm, leadership.
Mac begins to think twice about his initial decision to put Dakin in a leadership position. He now understands that Dakin's coldness is not cool-headedness. Instead, it's a kind of elitism that comes from his pride in his possessions. It's at this point that Mac tells Jim they have to get rid of Dakin:
"He's too tied up with his truck, and his tent, and his kids. He's too careful. London'ud have been the best man. London hasn't got anything to lose." (138)
Dakin's major problem, at least in Mac's eyes, is that he doesn't live up to the ideal of the commune. While it's clear that Dakin isn't a raving capitalist, he would certainly be a member of the Growers' Association if he could be. He more or less tells Mac that he doesn't like him or his "red" ideas—it's just that he's poor and doesn't have much of a choice:
"If I owned three thousand acres of apples, d'you know what I'd do? I'd get behind a bush an' when you went by, I'd blow your God damn head off. It'd save lots of trouble. But don't own nothing but a light truck and some camp stuff." (65-66)
So Dakin's a guy who straddles two unstable and unsustainable worlds: that of the impoverished worker and that of the outrageously wealthy and powerful landowners. Dakin can't last too long in this world while he does this.
And he doesn't. It takes only the destruction of his truck to make Dakin behave in unattractive ways in front of the men—and then he's dragged off to jail. His dreams of continued success—and more great camping stuff—are thus pretty well dashed.