Connor caused a lot of mixed feelings when he joined and his first day was in the middle of a very busy day. He took lead and this irritated a lot of the staff, including Will and Sharon.
In Malignant, Christopher Herrmann was brought in after being stabbed. Connor was the attending and according to 51, he delayed in treating Herrmann. This wasn't confirmed but Severide asked Jay to ask his brother about it. Will told Jay that he personally thought that Connor delayed. Severide then called Connor out in front of everyone, which upset him. He then figured out it was Will and they argued, and Will apologised.
Connor's background and family were revealed when his sister, Claire, came in with a friend who had been impaled. The friend was mutual and Connor decided to do surgery on him himself. His father, Cornelius, constantly called Connor out and said he wouldn't be capable of carrying out the surgery because he wasn't good enough. Connor refused to step down and Cornelius went to Sharon Goodwin, insisting that Connor not do the surgery, considering he was a big donor of the hospital and should have a say in it. Sharon replied that while she was grateful for the donations, she wasn't going to tell her doctors how to operate or take Connor off the surgery. Connor succeeded in doing it and in the end, Cornelius asked him to come back to the family business. Connor refused to.
Robyn's psychiatric problems get out of hand when she wakes up in the middle of the night screaming in the apartment. Connor goes to help but she is visibly scared of him, grabbing things to keep him away and ending up in the balcony. Connor tries to help, but she locks him out and tries to jump out of the balcony while he watches in despair.
In the finale, she was admitted to psychiatric care while Connor and Dr Charles argued over the best course of action for her when she is released.
After Robyn was admitted to the psychiatric hold after a breakdown in Connor's apartment, he and Dr. Charles were in disagreement over her wellbeing and who should make decisions for her. However, even after she was supposedly okayed by Sarah Reese, she experienced problems. She was under constant paranoia and having difficulty controlling her actions.
At the same time, Connor has difficulties with his new co-worker, Ava Bekker, who is constantly trying to challenge him and take his cases. This proves even more challenging while Robyn is recovering, because his attention is skewed towards her, leading to her trying to use Robyn to infuriate him. They later started to become friends.
In Ties That Bind, he was called by his father's security team to say that Robyn had been caught shoplifting at his store. She was upset and angry that she was doing these things but couldn't control herself. Cornelius told Connor she was bad for him, and he was angry, telling him that it wasn't her choice. However, Robyn was more upset about these issues and went to Charles for help. Connor later found a letter at home from Robyn saying she'd left. He was furious and argued with Charles about sending her away, but was told it was her idea and that she didn't want him to stop her. He was heartbroken.