Dally and Darry are similar in that they are both leaders. Though their styles and leadership qualities are different, the greasers look to them both for guidance. Darry's physical strength and size as well as his inner strength are meaningful to the other boys, and because Darry is older than many of the boys, he takes on the role of a father figure.

Dally, on the other hand, has a dangerous history of being in urban gangs and living a life independently of others, so his ability to survive means he knows something about how to look after himself. It is Dally's self-reliance that intimidates other greasers and inspires them to admire him and listen to him when he has advice to give. These leadership qualities aren't as obvious as Darry's, but they still exert power over the other greasers despite their rugged appearance.

Dally gives the boys, especially Ponyboy and Johnny, advice and support when they are in trouble. He coaches them on how to survive, and he gives them very specific information about where to go and how to look inconspicuous. Dally also models quiet, hard strength for the boys, which means he gives them an example of how to rely on oneself.

The Outsiders is a novel that is primarily based upon the strength of its characters. The characters of Dally Winston and Darry are similar in that they are both characterized as being extremely strong figures. They overcome their surroundings and never let their situation get the better of them. Ponyboy looks up to his older brother Darry as is seen by the nicknames he has for him. Dally serves this same purpose for Johnny. Johnny has no family and replaces that with the gang. Dally his his father figure. Dally, much like Darry with Ponyboy, does not want Johnny to "get hard" and lose that boyish innocence like he did so long ago. Dally is mean. This is why Ponyboy states that out of all the members of the gang, he "liked Dally the least". However, this is what he gives to Johnny and why Johnny admires him as he compares him to the southern gentlemen riding gallantly "into sure death" in Gone with the Wind.