How about if he plays for No Deal by default? Doesn't put a further extension on the table to the EU waiting for them to pull the trigger on us on 31st Oct. The "Mexican Stand-off" approach.
Yes, that's a possibility. But that approach could well trigger a vote of no confidence and the signs are that, if a No Deal was the favoured option, he'd lose a vote. I see reports say that something like 40 Tory MPs would vote against him - even if it's half that, it's a hell of a rebellion