Early in the game, Connor pinned himself as the antagonist of the season by targeting Nicole and Nicolas with the hopes of splitting them up before jury. Although his efforts succeeded, it wasn't without controversy. When Corey was almost backdoored Week 2, Connor, alongside Julia rounded up all of the houseguests who voted to keep Corey. After comments were made by Connor about Nicolas in that alliance chat, Sydney exposed them to both Nicolas and Nicole starting a movement against the majority of the house led by Sydney. When he won the Secret Dual Head of Household, Connor nominated Aly and Jack for eviction with a pointed nomination speech. For the majority of the game, it was assumed that Julia had won the Dual Head of Household due to the speech. When Sydney won Head of Household during Week 6 and nominated Connor for eviction, Corey used his Diamond Power of Veto on Connor, renominating Nicole, their target, in his place. Once Nicole was out of the house, Connor's side of the house had the majority going into the Double Eviction. However, when Sydney won Head of Household and nominated Connor next to Julia, the majority had to turn on one of their own. After losing the Live OTEV competition, his fate was sealed when he was nominated next to Andie and was evicted by a vote of 4 to 2. Throughout the season, Connor was known for interrogating people for their votes and fighting anyone who didn't side with him including Renee, Nicolas and Sydney.
Connor entered the Big Brother as not only one of the two returnees from Season 1, but also as the head of the Evil Team.
Immediately from when he entered the house, Mike called out Connor for being in real life friends with Ari within the first five minutes of the game. From then on out, Connor was tasked with making him seem as less of a target than he actually was. Despite winning four head of household competitions, Connor was only nominated one time besides at the Final 3. Rhea was the only person to nominate Connor during the entire game. Alongside Randy, Connor won the Battle of the Block and secured his safety for the week, fighting Rhea in the process. Though they fought initially and targeted one another for the next few weeks, they eventually set aside their differences and then worked together to get further in the game. Connor's pivotal moment in the game was when he decided to turn on Carson and Jacob and get them out during Week 10. After the Special Live Eviction, Connor eliminated all of his possible threats and was left in the Final 5 with all of his allies and didn't have to fight hard to make it to the end of the game. By laying low and letting Kaleigh and Justin fight one another, he was able to make it to the Final 3 with ease. The jury was fully supporting him and it seemed as if he was the clear pick for the winner when he fumbled during part 3 of the Final HOH competition and was subsequently evicted by ally Kaleigh and became the final member of the jury.