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It's not easy competing with a dead man. This isn't fair, Tony knows. Being dead is probably a lot harder, if it's anything at all. It can't be easy to have to watch every mistake ever made without ever being to try and fix them. But then, Tony has never been dead, so it's not exactly like he has a frame of reference here.
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When Tony was fifteen, he graduated from MIT with honors and invented the prototype for a new cellphone. When Steve was fifteen, falsified enlistment papers multiple times and got beaten up by bullies a lot. Tony got a brief nod and a that's the Stark way, maybe I'll take you out from dinner sometime. you'd like that, wouldn't you? before the phone rang. Steve gets billions of dollars spent on him for fruitless expeditions and a whole day devoted to him every year. Tony knows that he is not supposed to judge other people solely by their intelligence (or at all, really, Jarvis likes to remind him), but he's pretty sure there's an injustice of some magnitude involved here.
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The funny thing is that when Steve was still able to make mistakes (maybe, Tony can't imagine Captain America ever screwing up the way Tony can), Howard had hated his drawing. It was pointless, it was unheroic, it was making him melancholy and broody and antisocial (personally, Tony thinks that these are things you are born with, but he knows better than to say so). Now there isn't a room in the house that isn't dominated by at least one of Steve's carefully framed sketches. There are lots of them to choose from; when Tony had been younger, he'd thought he might apply Howard's goal-orientation: one award or accomplishment per sketch. Fourteen years and sixty-eight accolades later, he has yet to catch up, and the only walls Tony dominates are in his workshop.
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Other than sharing a gender and a man named Howard Stark, there are no similarities between Steve and Tony. Steve draws, Tony invents. Steve is (WAS!) is blond and tall and supersoldiersteroids, Tony is dark and only human and two inches too short to fill Howard's shoes. Steve is shy and retiring and just as happy as a wallflower as the Star-Spangled Man. Tony is loud and magnetic and doesn't know how to exist without an audience. Steve was a dutiful vegetable-eater and thought kissing was something to be hoped for after the third date, Tony has a sweet tooth the size of candy mountain and fucks anyone halfway attractive without regard for age, position, gender, or publicity. There is absolutely no reason that Tony should remind anybody of Steve. There is absolutely no reason that every time Howard looks at him, Tony knows that he is seeing Steve.
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Feeling like you have to apologize for not being somebody else is probably on the List of Things That You Shouldn't Feel. Tony is pretty sure of this. He has yet to learn all of the feelings that mean something's wrong with you, partially because the list is very long and he's pretty sure people keep adding to it when he's asleep, partially because there's also a subcategory titled List of Things That You Actually Should Feel But Say You Don't, and this list is both the longest and the hardest to figure out. He thinks the somebody else thing is maybe on this list, which means he can't actually ask anyone about it. It's not until he's eighteen that Tony realizes maybe the subcategory should properly have been named, List of Things That Howard Thinks You Should Feel But Won't Admit It..
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You can't beat a dead man. Tony realizes this on the tenth November 23rd of his life, shaking and crying in Howard's lap. For the first and last time in either of their lives, the two Stark men cry together, bottles littered around the armchair. They are both crying for the same man, and this brings them together in a way they have never before known. They are crying for different reasons, and this brings them apart in a way that can never be fixed.
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People think Tony is entitled, that Tony is spoiled. they think that he has gotten everything he has ever wanted. They think that he has never learned to take no for an answer. Pepper thinks Tony is stubborn, that Tony is unstoppable. She thinks that he has no idea of the impossible. She thinks that he has never learned to give up. People and Pepper are both right. Tony is a selfish son of a bitch who knows what he wants and won't stop until he gets it. The only exception was, once, Captain America, because even Tony isn't stupid enough to think he's above death. As long as Steve Rogers is dead, there's no way Tony can prove that he's all the son Howard needs.
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When Sleeping Beauty turns up, frozen in ice and still maddeningly unwrinkled and super-steroided, Tony takes a trip to Howard's grave and stands in front of it for a long time. There should be something to say here, he thinks, something deep and profound and so cutting that Howard wouldn't be able to brush it off or say anything back even if he were alive. He opens his mouth and finds himself laughing. it's one part hysterical and three parts ironic and six parts fuck you, and when he walks back to where Happy is waiting for him, he's still shaking with the afterglow.
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Unbearably, Steve Rogers is not perfect. He favors his left side when he's sparring and leaves his brussel sprouts on the side of the plate. He laughs too loudly at not-funny jokes and always sings three notes off-key and can be a sanctimonious prick when he's not paying attention (and even when he is). IMAX movies give him a headache and Tony suspects that he takes a sadistic glee in the fact that he's the only member of the Avengers (or, most likely, in all of SHIELD) who can function without caffeine in the mornings. In many ways, he is the biggest anticlimax of Tony's life. Sometimes when Rogers is at his pompous worst, Tony wishes Howard were still alive so he could see what a goddamn boring asshole Captain America can be. Then he remembers that Howard did actually know what a goddamn boring asshole Captain America could be, and it leaves a sour taste in his mouth.
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SHIELD has a chaplain (and a priest, and a rabbi, and an imam, and a Grand Pookah of Timbuktu, probably), but Tony never bothers visiting him. Tony isn't much for things that can't be explained by science, or the idea that everything is predestined, or letting someone else have control of his life. The idea of an afterlife, though, is a nice little idea, and sometimes when Coulson is being especially unremarkable and pedantic, Tony allows himself to zone out and imagine Howard reaching the next life, only to discover that the man he spent all of Tony's life mourning isn't waiting for him. It leaves a warm, fuzzy feeling in his arc reactor that Tony imagines Captain America gets when he helps old fucking ladies across the street, or something.
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Rogers really likes to generalize, Tony finds out. "is everything a joke to you?" he demands on what, their second meeting? "not everything's a question of style, Stark," he states on their fifth meeting. "everything's about you, isn't it?" he accuses on their thirteenth meeting. "why does everything have to be a competition with you?" he asks (which is not at all the same thing as demanding, finally, finally) on their twenty-sixth meeting. Tony doesn't even bother answering that as he drops his water bottle (on Rogers' foot, he yelps in an utterly undignified and unpatriotic way, and a corner of Tony's mouth twitches) and strides out.
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Steve is a virgin, and Howard was too busy pining after his lost soldier to ever cheat on Maria, which means that sex is an unconquered territory for Tony. It's the one area in which neither Captain America nor Stark, Sr. has ever stepped foot before Tony, which means it's the one area that's never been bothered (ruined) by competitiveness. There's nothing Tony has to prove in bed, because there's no way he could be worse than a blushing boy from the 40's or an alcoholic who was barely adequate to produce one boy. This makes it the ideal spot to hold an armistice that will mark the end of a war that lasted forty-three years.
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It's not easy competing with a dead man. It's harder to stop competing with a living one. It's hardest to try loving a man who was dead and now isn't. Tony thinks, though, that he might be able to. After all, he's never been one to take the easy way out of anything.