The Prime Minister has repeatedly promised to deliver Brexit on Halloween - “no ifs, no buts”.
Mr Johnson said he would rather be “dead in a ditch” than seek a fourth extension to Article 50 from Brussels.
But at the same time, the embattled Tory leader has promised to obey the rule of law - and that includes recent legislation requiring him to delay Brexit rather than leave without a deal.
As a result, the Prime Minister’s approach to solving the Brexit impasse is held back by one major contradiction.
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Mr Johnson has maintained that he would rather the UK leave with a deal on Halloween that without one - but he has continually butted heads with Brussels over the issue of the Irish backstop.
Mr Johnson is demanding the Irish backtop - the mechanism to prevent a hard border between Ireland and Northern Ireland - is removed from the Withdrawal Bill entirely - despite various figures, including European Parliament president David Sassoli, saying there will not be a deal without a backstop.
The EU has also rejected the UK’s plans to replace the backstop.
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On Thursday, the EU’s Brexit coordinator Guy Verhofstadt, reiterated the comments.
He tweeted: “After meeting Michel Barnier this morning, Parliament reiterates the need for a legally operational solution to the situation Brexit created in N-Ireland.
“To preserve consumer safety, to protect our businesses and preserve the peace. So far UK proposals fall short on all 3 fronts.”
Despite Brussels’ stance, Stephen Barclay is to meet Michel Barnier on Friday for crunch talks.
After meeting Mr Barnier earlier in September, the minister said: “There is a shared desire reflected in the meeting today to secure a deal.
"There is a clear message from (European Commission) President Juncker and from the prime minister that a deal is doable.”
What happens if he doesn't get a deal?
The new bill passed through Parliament - known as Benn’s law - requires Mr Johnson to seek an extension if a deal hasn’t been agreed.
The law will force the PM to seek a delay on Britain’s exit until 31 January 2020, unless a deal or no-deal exit is approved by MPs by 19 October.
A majority of MPs have clearly said no-deal should be removed from the negotiating table
Mr Johnson reportedly told Tory members he was willing to ignore the legislation, writing: “They just passed a law that would force me to beg Brussels for an extension to the Brexit deadline. This is something I will never do.”
But if the Prime Minister doesn't secure a deal, it's not clear how he could dodge asking for an extension without breaking the law.
The ex-director of public prosecutions, Lord MacDonald, said if the prime minister did not comply with a new law compelling him to extend the October 31 deadline he could be in trouble.
Lord MacDonald told Sky News: "A refusal in the face of that would amount to contempt of court which could find that person in prison.”