Continuity mistake: When Teddy's kids are lying dead on the grass, the position of the girl's arms keeps changing between shots.
Continuity mistake: During Teddy's interrogation of Bridget Kearns, she takes Teddy's notebook and writes something on the page to the left. Yet, when he shows the notebook to Chuck Aule, all of Bridget's writing is on the page to the right.
Continuity mistake: After Teddy takes his dead daughter's shoe off, its position changes between angles.
Continuity mistake: When Teddy's kids are lying dead on the grass, the position of the girl's arms keeps changing between shots.
Dr. John Cawley: We don't know how she got out of her room. It's as if she evaporated, straight through the walls.
Trivia: During the ferry approach at the start, we are shown Shutter Island. In actuality this is a combination of Peddocks Island (the decaying brick buildings), Maine's Acadia National Park, Massachusetts' Medfield State Hospital, and Turner Hill Country Club's Rice Estate (located in Ipswich, MA), which were combined via CGI. Additionally, the mountainous region of the island (shown as the ferry approaches) was also CGI, and added in post-production.
Question: The woman that writes "run" on Teddy's note pad, was Ben Kingsly trusting this "crazy woman" not to tell Teddy or even let it slip that the whole thing was set up for him? Same question goes for every other crazy person in the institute that Teddy speaks to.
Chosen answer: The other patients were not let in on the arrangements. They would have had no reason to suspect that anything at all had been set up for Teddy. As far as they're concerned, if they're cognizant enough to be concerned at all, Teddy's just another crazy guy acting as crazy as all the rest of them.
Answer: I think Mrs Kearns is in on it. We see her get a little flustered when she is asked about the doctor, who we find out later is sitting right there. Also, she gets uncomfortable when Teddy brings up Andrew Laeddis. She even tries to warn Teddy. I just discovered this recently when watching with the subtitles, but when Teddy comes back from the cave, Mrs Kearns can be heard saying "I can't remember what I'm supposed to remember", likely referring to the script she was supposed to stick to.
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Answer: Teddy belonged in Ward C. He would have never met any of the patients.