Hi Hernandez, Here is a quote from Raymond Murphy’s English Grammar in Use: “You can also use ‘would’ to talk about things that happened regularly in the past.” (Unit 36) I looked this up to check my native speaker’s intuition that yes, ‘would’ sounds natural for the sense that Trump repeatedly/habitually did this during that period; the simple past makes sense and is used but doesn’t give that sense of regular, repeated action. What doesn’t seem necessary to me is “already”, because you have the adverb phrase at the start of the sentence telling us about time.

I would use: "T. was already speaking out against..." or "T. had already spoken out against..."

Trump already spoke out...................