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A funny thing happens during the Brexit transition period: if we get to 1 July 2020 and we haven't asked for an extension, that's it... No amount of fudging, pleading or begging can stop us crashing out of transition (we're already out of the EU, of course) on 31 December 2020.
So in practice there's only 5 months to do a deal. Because the only sane, rational response to not achieving one by 30 June is to ask for that extension.

That's the theory. The wrinkle comes because the Tories are *so* deluded they may take the risk and blow past 1 July.
But 31 December 2020 deadline is then fixed by our missing the deadline. No matter what, that's it.

In other words, we'll be just 6 months from damage similar to that a no-deal Brexit would inflict.
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