I think leaving on october 31without a deal puts the uk in a weak bargaining position with other trading nations.
Winston Churchill was not a successful peace leader he was someone who managed to win a war with the help of some friends, particularly stalin and the usa,and some help from hitler who made the same mistake as napoleon, fighting on two fronts ,he was lucky, hitler was a poorer war leader than him ,that does not make him a good war leader, he was quite good at speeches and had some good speech writers but tactically he made at least one serious miscalculation