Great question.
1. O'Brien is busy "healing" Winston in the Ministry of Love when this quote is shared. I am sure Orwell struggled with this line as I believe he wanted O'Brien to strip away every thread of hope that Winston was still hanging on to. Winston hopes for a future in which the party is defeated, but instead the party will prove to be indefatigable. The boot represents INGSOC and the face is all of humanity.
2. This quote is stated by a nameless prole. One of the mindless masses who shares, "We didn't ought to 'ave trusted the buggers". Perhaps Orwell wants us to consider that once a freedom has been taken or given away, it is just about impossible to regain.
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