Tony was genuinely hoping Steve would just make the easy choice to come with him. It wasn't like he had anything better to do; it looked as though he was living the exact same life he would be with the Avengers, except with a crappier wardrobe and probably terrible food. How did a famous criminal get by? Did he have a goofy disguise for his dayjob at a McDonalds? A fake bank account? Fraudulent tax forms? None of that sounded much better than stealing for the Righteous and Just Moral Police. But then, those sort of rules didn't apply to Steve, did they? Just everyone else, so he could sneer judgmentally at them when they fell from grace.
Now Tony was pissed. He would save himself the 'trouble' by seeing how well Cap handled being in the air without leverage. Much like Iron Man had hauled the old man out of the fight, he burst toward Cap with a flare that made several of the fallen guys groan, slamming into him around the middle to carry him up into the air. "Uh, sorry, change of plans. Both of you are coming with me."