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Notes -
His strategy with Ukraine appeared to be to soften the USs pro-Ukraine position enough that the US could reasonably act as a third party to the negotiation. This naturally involved becoming harsher towards Ukraine. It didn't work, because Putin was intransigent and possibly took this (as many of Trump's opponents seem to have) as Trump being a pushover. But it's certainly a strategy that had a chance for success. It even seemed to have worked in Gaza, where the ceasefire came right after the Trump administration got publicly pissy at Israel over attacking in Qatar.
A risk raised by his domestic opponents when he suggested his solutions.
Well Israel, the stronger party here, is closer to Ukraine than to Russia so it isn't really the exact same problem (putting aside whether Trump's vocal support emboldened Israel into that blunder or if the later apology was all theater)
No, his domestic opponents didn't stop with saying that Putin would think he was a pushover. They said he WAS a pushover and was going to give Ukraine away. He did not. The negotiation failed, but so had all previous attempts.
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