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The real problem is those (principally civil servants) who negotiated with the EU either did not have a clue about how to negotiate or negotiated with a view to getting such an unsatisfactory agreement that they would succeed (they hoped) in getting the Leave vote reversed.
Two simple errors.
The EU gave us a useful red line over the Ireland border; our answer should have been we will not erect a border, whether you do is up to you but if you want no "hard" border then there will have to be an agreement, and these are our terms.
A transitional agreement should be about how we get from "A" to "B". The EU have refused to negotiate where "B" is, so any transitional agreement is bound to be a mess. The negotiators should have understood that the terms outlined in the transitional agreement are a strong indicator of what the final agreement can be expected to look like so not wonder it is unsatisfactory.

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