With the man mooted in some quarters as a potential future Prime Minister returning north of the border, the Scotsman recalls his first foray into Scottish politics.
Rees-Mogg was just 27 when he was selected by the Conservatives to contest Central Fife – a traditional Labour seat – at the 1997 general election.
The Etonian travelled to Scotland with a mind to hitting the campaign trail, but his upper-class background soon put him at odds with a largely working-class electorate.
The son of late Times editor William, Rees-Mogg made the inauspicious decision to knock on doors in the former mining town of Leven on the Fife coast.
But reports quickly emerged of the English candidate taking the family’s nanny, Veronica Crook, in tow during canvassing while driving around the back streets of Fife in a Bentley.
Rees-Mogg turned into cannon fodder, particularly for the tabloid newspapers.
He was photographed in a pin-stripe suit visiting the doors of constituents in the Broom estate in Leven.
Declarations by Rees-Mogg that people on benefits were the “scourge of the earth” didn’t help his position.
Adding to his back story were reports of Rees-Mogg having to be saved by his Labour opponent Henry McLeish from being beaten up.
McLeish told the Daily Record earlier this year: “At one point, somebody threatened to come onto the platform and beat him up.
“A touching part to that was that after saving him from a potential duffing up, his father, the very distinguished editor of the Times, William Rees-Mogg, sent me a letter thanking me for how I’d managed to protect him, for which he was very grateful.
“It was a delightful letter, basically saying ‘I don’t often write to Labour MPs, but I would like to thank you very, very sincerely for the way you looked after my son’.
“Jacob was like a fish out of water and clearly bewildered by places like Methil and Kennoway.
“I did not get the feeling he was the dangerous ideologue extremist we know him as today.
“He was reasonably well behaved in my company because I think he was in fear of his life.”
“The fact he is looked upon by some as a future Prime Minister seems well beyond the realms of comprehension. I never even thought he’d ever make it as an MP.”
Rees-Mogg later clarified he had been driving his mother’s Mercedes Benz during canvassing – and not the Bentley that soon made him a source of public ridicule.
“The nanny bit is right,” Rees-Mogg confirmed in 2013.
“Of course she came canvassing, she’s part of the family after all. She’s been with us for 47 years.”
But despite his family owning two classing Bentleys at the time, the former investment banker stressed: “We took my mother’s Mercedes Estate.
“I don’t think a Bentley’s a suitable campaigning car. It was the petrol consumption – six miles to the gallon.”
Rees-Mogg, now 49, would go on to finish a distant third in polling for the electorate, receiving just 9 per cent of the votes in Central Fife.
It would prove a disastrous election in Scotland for the Conservatives.
No new Conservative MPs were elected in Scotland that year, with the Tories suffering their worst electoral defeat since 1906. The party lost all its seats in Scotland.
Rees-Mogg refused to accept his background was an issue.
He said at the time: “Nobody says to Tony Blair in Sedgefield ‘you’re Scottish, so what are you doing in an English constituency?’. Or to Teddy Taylor in Southend.
“I suppose I’m Teddy Taylor in reverse. He has as much connection with Essex as I do with Central Fife, but we’re both campaigning on national issues that affect the whole country. I only had one person who shouted ‘go back to Cornwall’, which was rather odd because I’ve no connection with Cornwall.”
Rees-Mogg could claim to having had the last laugh.
He was elected as MP for North East Somerset at the last general election and has now emerged as the country’s political face of Brexit and a potential future challenger for the leadership of the Conservative party.