On Christmas Eve, Sam leaps into Reginald Pearson who is the valet to business tycoon Michael Blake. Michael is a thoroughly unpleasant man (though he is opposed to firing Sam despite his incompetence as a valet and his meddling in Michael’s personal life) who is planning on tearing down a salvation army building in order to build Blake Plaza. He also just happens to have very similar brainwaves to Sam and so is able to see Al until Al changes the frequency slightly so that Michael can no longer see him. Sam is sympathetic to the salvation army and so promises Captain Laura Downey that he will find a way to save the building…with her help, of course.
When Sam is ordered to sort through Michael’s suits to find which ones to save and which to give away (with heavy input from Al as Sam knows nothing about clothes), he finds a box of memories in the closet which reveal that Michael changed his name and used to be a poor orphan living on the same street as Blake Plaza is to be built on and that he’s trying to show the world just how far he has come by building the tower there.
Sam convinces the chauffer to let Sam drive Michael to his meeting and ends up taking him to the salvation army building. He stops the car and one of the local kids comes over and lets the air out of one of the tires to give them an excuse to stop. When Michel gets out (after wondering how Sam thought this was a good route to get to the meeting he had) he is assaulted by memories of the past, aided by several children playing and calling someone by Michael’s original name. Captain Downey appears and denies having seen the boys. Caught up in nostalgia and charmed by Downey, Michael happily tells her about growing up here.
When they stop to buy chestnuts, Michael recognizes the vender as Max Wushinski, an old friend that he had lost touch with. The two reminisce for a bit and then Michael asks what happened to his old best friend. Max is forced to tell them that he became an alcoholic and killed himself after losing his job when the plant became automated. As Michael made his money off of laying off workers like this, he is deeply upset. He tries to pay extra for the chestnuts but Max just tells him to go.
Michael storms off and then sits in his apartment getting drunk and so Sam thinks that he’s failed. Al believes that this is actually a good sign and that Michael is thinking about what he is doing and so they put phase two of their plan into action. Sam tells Michael that he feels sorry for him because, for all of his wealth and power, he’s still missing something from his life. Michael angrily asks how he would know and Sam bets a month’s rent that he can prove it.
Sam takes Michael back down to the site of the future Blake Plaza and has him put his hand on the side of the building, telling him that that path is just cold and Michael retorts that he’s had people who loved him but they all either died or left him and this building and his empire won’t. Before they can leave, though, they hear singing coming from the salvation army building and come in. Michael is once again caught up in nostalgia as he joins the festivities and really starts to open up to Downey.
Unfortunately, a little boy comes over to give Michael a Christmas present and Michael recognizes him as one of the children from earlier and realizes that this is an elaborate charade to make him change his mind. Furious, he storms out and tell Sam that he had better hope he didn’t still want to fire him in the morning.
Sam was discouraged but then he remembers that Michael can see Al and sends him in as the third ghost. Al chooses to go all out and dresses up as Jacob Marley, which Michael calls him on. Because Michael saw him earlier, he doesn’t initially believe that Al is a ghost and keeps insulting him. Eventually, he tries to punch Al and falls right through him. After that, it doesn’t take long to convince Michael that Al is really a ghost. Michael calls for Sam to get rid of Al but Sam pretends he cannot see him.
Al takes Michael to the Salvation Army building and shows him the future. Michael is delighted at the picture of the finished Blake Plaza but then he sees a news report from 1975 featuring an older, bitterer him declaring bankruptcy. He sees that his tower has been renamed and that he eventually jumped from the top of it into oncoming traffic. Michael is horrified and breaks down sobbing.
Sam convinces Michael that it’s not too late to change and a bright star leads Michael back to the salvation army’s door and Downey lets him in. Al reveals that the two of them marry in six months and have three kids. Michael still builds his tower but he gives the entire first floor to the salvation army. Sam wonders if Michael would have knocked on the door if Al hadn’t put the star there…but Al says that he didn’t.