Lisa and Beth try to find out why Matthew has gotten a brother from the Big Brothers Big Sisters of America. Dave seemingly becomes paranoid when Bill suggests Lisa has a secret new boyfriend, which leads Bill, Joe, and Mr. James on the hunt for whom the guy is.
Using information secretly collected by secret office observers, Mr. James notices Dave and Lisa's productivity levels were higher when they were dating, so Mr. James set out to try and get them back together, but when that fails, Bill steps in. Mr. James gets Matthew a small red car for his birthday, which he drives around the building and meets a girl with.
After a co-worker nobody knew dies in a freak incident involving a copy machine Joe modified, Joe blames himself for the man's death. An old college friend of the departed shows up wanting to know more about Ted, and the staff, lead by Bill, make up lies.
After Bill's funeral, the staff deals with their grief. Catherine comes back to read some private messages as part of Bill's last will. Matthew wants to believe Bill is still alive and traveling the world.
Dave thinks its time to hire Bills replacement. When the staff resists he considers going with a long time friend of Bill, Max Louis. As it turns out, Max is a horrible radio personality and gets fired from every job he has. Joe needs to fix all the computers in preparation for Y2K. Electronics around the office randomly explode.
Dave is more stressed than usual, so Joe decides to make him a white noise machine for relaxation. Dave loves it and eventually becomes so mellow he refuses to work. Max infringes on Lisa's special show "This Day in History" by broadcasting ridiculous live interviews with historical figures and twisting of facts.
Mr. James is arrested and held for possibly being the legendary bank robber D.B. Cooper, and while he's out his office has called in Johnny Johnson to fill his place, much to Mr. James' dismay; Johnson quickly makes positive impressions on the staff. Afraid Lisa is uncovering to much damning evidence on Mr. James, he assigns Matthew to the story.
With Mr. James on the loose after breaking out of prison, Dave and Lisa must try to get the green duffel bag away from Johnny Johnson, which is made harder since Lisa has the hots for Johnny. The rest of the staff refuses to believe Johnny is evil.
After beating the D.B. Cooper case in court, Mr. James comes back to find he cannot get rid of Johnny since he was made CEO in Mr. James' absence. Now the staff and Mr. James must find a way to get back Jimmy's empire.