I’m fully convinced, now more than ever, that Chase is involved with Helix. And the best part is he probably only had to make one small move to set this play in motion. All he’d really need to do would be to tell Helix who Felicity was, because he’d know Helix would recruit her and he’d know Felicity would say yes.
Kidnapping Susan instead of Felicity meant that Felicity was free to help Oliver get intel on Susan’s location, which Chase knew would mean digging herself in deeper with Helix, which would mean getting herself in trouble with the law somewhere down the line. He WANTS Felicity to work with Helix, because he WANTS her to break the law and he WANTS her to get caught. By keeping this from Oliver, Felicity’s driving a wedge between them, which means Oliver won’t see it coming. Chase knows how much it will hurt Oliver to see Felicity behind bars and feeling like he’s to blame for it.
So even though Chase knew it would hurt Oliver more if he kidnapped Felicity instead of Susan, he knew that NOT kidnapping Felicity would eventually hurt Oliver even more down the line.
Felicity’s involvement with Helix is one of those “ten steps ahead.” He’s playing the long game with Felicity. To borrow the chess metaphor, he’s going to strike the Queen last, and if Felicity continues to keep this secret from him, he’s going to be completely blindsided by this move. And I cannot WAIT to see this storyline continue to play out.
EDIT: Holy hell I just thought of something else. What if Chase kidnapped Oliver for this same reason? What if Chase kidnapped Oliver because he knew Felicity would move heaven and earth to find him; that she would dig herself in even deeper with Helix in order to save him.
What if kidnapping Oliver has nothing to do with Oliver and everything to do with Felicity?