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In War for the Planet of the Apes, the white ape Winter is on Caeser's side. After the first battle, they capture some soldiers and the traitor gorilla Red. Winter escorts him out and eventually claims he got attacked and Red escaped. Later in the movie, we see that Winter also joins the humans, and he explains that

Red promised me the Colonel would spare me if I joined him

Me and my mates got into a discussion on the subject of whether Winter had allowed Red to escape or not.

I seems strange to me that he would have, since by then he wasn't that scared of the humans, and also because he would let the other ape run away but still linger on for a while after Blue Eyes (Caeser's son) returned.

However, the way it is shown in the movie, it seems that Red was the once who convinced Winter to escape, and that it was all a big plan from the start.

Having only seen the movie once, maybe I just missed something. Anyway, did Winter cave under fear and join the humans' side when he let Red run away, or did Red actually manage to escape and Winter just decided to join them later?

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The implication is that Winter was already afraid of dying. When Red first talks, while being held captive by Caesar's forces, he recounts how the Colonel will kill all of Caesar's apes. The camera cuts to Winter who is visibly shaken. It clearly implies that he believes it to be true. He then hesitates in taking Red away when ordered. His later appearance with the Alpha Omega troops spouting the same rethoric that Red said, solidifies the implication. He was convinced before Red escaped, and thus helped that happen. It is clear foreshadowing. The movie shows us an tight shot of winter to solidify this, showing the audience that Winter is conflicted and afraid. Having that moral dilemma happen off camera without any hint to the audience would be bad writing/storytelling.

The movie presents multiple of this turncoat moment for multiple characters. Red at the end, the crossbow soldier who was presented as maybe turning while Caesar was interrogated but then not. And most importantly, Caesar's struggle with his revenge or staying true to his own convictions. Winter is presented as a contrast to Caesar who would not give up his fellow apes to save his own skin.

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