After the events of the third game, Bentley sees that Sly has amnesia and after some months pass, the team goes their separate ways, leaving only Bentley and Penelope behind. He reinforces the Cooper vault, as well as inheriting the Thievius Raccoonus, becoming the first non-Cooper to write in the book.
He and Penelope start developing a time machine, when Penelope mysteriously vanishes. This also makes Bentley notice that the pages of the Thievius Raccoonus start disappearing, page by page. This prompts him to get the team back together, and adjusting the time machine to fit onto the van, allowing them to go back in time to save Sly's ancestors.
Bentley did some work in the field, and it wasn't until Medieval England that he found out where Penelope was. As it turns out, she was disguised as The Black Knight, with Bentley being brokenhearted for a bit. During the boss battle with her, Bentley arrives in time to stop Penelope and defeat her in a fight of robots.
