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frank9755
If my maths is correct (it almost certainly isn't but let's have a stab anyway) CRR going from 0.00267 to 0.00543, which is a doubling the watts required to push the tyres is ~1mph speed difference at 150W.
So, up to maybe 20mi per day slower, assuming 20hrs riding.
Given the rate at which the gap closed though I find 'slow tyres' to be unlikely. What is more likely is fatigue and maybe him cracking a bit -because- of the tyre issue taking away a bit of his buffer. That's certainly possible.