Like Marlon Brando in On The Waterfront, Gail Wynard could have been a contender. Wynard had so much potential, and he could've given Roark a run for his money in the hero department. But Wynand couldn't quite make it.
A self-made man, Wynand at first seems like the poster boy for living the American Dream. He grew up in a rough slum and managed to work (and fight) his way to the very top. But Wynand embraced a bad system, largely out of cynicism:
Gail Wynand delivered his paper, body and soul, to the mob.
"I am serving that which exists on this earth in greatest quantity. I am representing the majority—surely an act of virtue?" (3.1.169)
Society might be partly responsible for Wynand's life choices, but he definitely opted to embrace a bad system. His trajectory from the streets to a swanky penthouse apartment has made him too callous and cynical to battle for individualism like Roark does. He's beaten down.
Also, unlike Roark, Wynard is a dynamic, three-dimensional character. His story is a roller-coaster: he grows up on the mean streets and makes good, he becomes embittered by the crass world of the media, he meets Dominique and Roark and starts to feel yearnings towards integrity. He even defends Roark publically, only to take back his defense when the social pressure gets too strong.
Ultimately, Wynard doesn't have the brass to stand alone against society. He's weak in comparison to Roark, and his weakness helps Rand drive home her Objectivist viewpoint that caring about society in any way, shape or form, is symptomatic of spinelessness.
Fun fact: Wynand has a bunch in common with media mogul, William Randolph Hearst. Back in the late 1800s, Hearst helped popularize so-called yellow journalism. This brand of journalism involved printing highly sensational stories to try to up readership. Sounds like The Banner, right?