If Oliver had to join the legends for a mission, let's say in season 2, before the more crazy stuff (or later, with the craziness if you prefer), how he would react? Would he take a step back and accept Sara's leadership? Would he be a team player? Would he allow himself to have fun or it would be all business for him?
Oh wow, that is a great question and one I've wondered about many times.
I think it depends on why and when he joins the Legends. If we go with Season 2 of Legends, which would be Season 5 of Arrow it depends when exactly he joins. I think after he decided to hang up the hood would make sense fot this hypothetical.
So, in that scenario he's in a really bad space physically and mentally. I could see him seeking out Sara because she understand what it's like to feel lost. And she got lost and ended up finding her purpose. Oliver would definitely let Sara take the lead and follow her. He might have some issues with her team and the way they operate but he trusts Sara, her judgment and that she knows what she's doing.
I think at first he would struggle with how different the team dynamic is and to find his place. But, huge but, whild the Legends are less structured when it comes to plans, they respect and don't question Sara's leadership which is a contrast to Oliver's team. I think it would be an eye opener for him. Sara's team trusts her, while Oliver's team doesn't trust him.
I think eventually, he'd take Sara's lead and ket himself have fun. He's relaxed and himself around Sara and he'd soon realize her team doesn't judge and accepts people the way they are and that would be the moment he eases up and has some fun.
I hope this makes sense and feels realistic. It's my opinion and how I'd see it.
But if anyone but Sara were leading the Legends things would be way different. Oliver trusts Sara and her judgment. He knows her. He understands her and he knows how far she's willing to go for her team and how serious she takes things, even if it doesn't seem that way.
Does that make sense?

















