The 8 Biggest Politics Betting Upsets In History

Betting on politics can be tricky business. They say a week is a long time in this game and betting sites know all too well not to bank on the favourite winning every election, or a sitting prime minister remaining in the job too long.

Down the years there have been some major politics shocks that have rumbled the bookies and earned shrewd punters a small fortune.

We’ve been using UK bookmakers for decades but it’s only in the past 15 years or so that punters, as well as bookmakers, have been able to react to political events in real time and take advantage of the change in odds. 

From Donald Trump’s shock presidential victory in 2016 to Margaret Thatcher resigning three years after her third election victory, life is never dull in politics.

Here are some of the biggest against-the-odds shocks in political betting history, starting with the most recent.

Conservatives Hold Johnson’s Old Seat

In June 2023 Boris Johnson quit as MP for Uxbridge & South Ruislip in disgrace after being found to have lied to the House of Commons over the Partygate scandal and sought to pressure the committee that looked into it. 

His resignation triggered a by-election and Labour’s Danny Beales was expected to walk into the seat.

Political betting sites had Beales at odds-on to win the election, while the Conservative candidate Steve Tuckwell was out at 10/1. Remarkably, Tuckwell kept the seat blue by fewer than 500 votes.

The campaign centred around the Ultra-Low Emissions Zone expansion from London into the constituency, and the Conservatives fought hard against it. Enough car owners voted against Labour to secure a remarkable win for the Tories.

Flip Flop On Erdogan

New betting sites really did get the 2023 Turkish presidential election badly wrong in their predictions. 

They initially set Recep Tayyip Erdogan odds of 1/6 to retain the presidency, failing to notice that voters were turning against him following two devastating earthquakes in the country.

Erdogan failed to win the presidency on the first round of voting, which caused bookmakers to flip their odds to rival Kemal Kilicdaroglu. Indeed, Kilicdaroglu was at one stage the favourite to win heading into the second round.

And then, Erdogan shored up his support to win the contest and remain president. The bookies had flipped one way and then the other and got it wrong both times.

North Shropshire Betting Shock

Another big by-election victory came at the very beginning of the period of sleaze that would come to define Johnson’s government.

Back in the autumn of 2021, Owen Paterson quit the House of Commons after being banned for breaching lobbying rules.

Paterson walked after the government failed to rewrite the rule book that would have ensured he could remain in Westminster without his ban. Voters didn’t like this one bit.

Betting apps had the Conservatives at 1/5 to win the by-election, with the Lib Dems at 9/1. The presented a likelihood of 83% that Tory candidate Neil Shastri-Hurst would beat Helen Morgan.

Yet over a six-week political campaign the Lib Dems piled resources into the constituency, while the national press exposed various controversies within the heart of Johnson’s government.

Those issues - such as Christmas parties being held at No. 10 during coronavirus lockdown in 2020 - turned the public against the Tories. 

It resulted in Morgan winning the traditional blue seat by more than 5,000 votes and giving punters who wagered against Shastri-Hurst profit of nine times their stake.

Trump Beats Clinton

Donald Trump is said to have been as shocked as anyone when the exit polls came in, and it was revealed to him that he’d beaten Hillary Clinton to the US presidency in 2016. He hadn’t ever planned to be president, and nor had the bookmakers.

Pollsters gave Trump a 13% chance of winning the 2016 US presidential election betting against Clinton. That was how confident they were that the Democrat would win.

Yet bookmakers priced Trump at a leaner figure, around 35%. Granted, the bookies didn’t consider him the favourite, but they sensed an upset was possible. It turned out some very smart punters were right, and they banked him to win at around 15/8.

Incredibly, one punter in the UK even wagered on Trump at odds of 150/1 three days after the businessman entered the contest for the Republican nomination.

Brexit

2016 really was a weird year for politics. The odds of the UK remaining in the EU in the days leading up to the Brexit referendum were as short as 1/4. 

That suggested a 76% likelihood that the country would vote to remain in the single market.

What pollsters, bookmakers and UK prime minister David Cameron didn’t realise was that there was a groundswell of fervour for Brexit. 

Those who wanted to leave the EU got out and voted. Those who didn’t even know what the vote was about stayed at home, as a results Vote Leave won by 52-48%.

Bookmakers took more than £100m in wagers on the Brexit referendum, and coughed up on odds of 3/1 on Britain’s exit from the trading bloc. It proved to be lucrative for those who wagered against the grain.

Corbyn Grabs Labour Leadership

Like Trump winning the US presidency, Jeremy Corbyn threw his hat into the 2015 Labour leadership battle not expecting to win it. He was seen as the ‘token lefty’ amongst a sea of Blairite candidates, yet he stormed the vote to take over.

The Week reported in August 2015 that numerous bookmakers had Corbyn at 100/1 to win the leadership contest. 

His victory caused a shift in party policy that would help the Leave vote and cast Labour into opposition for at least nine more years.

Corbyn came close to defeating Theresa May at the 2017 general election, but then suffered a crushing defeat to Boris Johnson two years later. Sir Keir Starmer is still trying to resurrect Labour’s reputation.

Major Loss In 1993 Christchurch By-Election

John Major’s government was about to begin its slide in the mid-1990s when Diana Maddock of the Liberal Democrats rumbled Conservative candidate Robert Hayward and earned a 38.6% swing in the 1993 Christchurch by-election. 

Maddock’s victory remains the largest swing against a sitting British government since 1918.

Wilson Beats Hughes

Republican Charles Evan Hughes was expected to win the 1916 US election and bookmakers in New York had him down as the big favourite.

Incumbent Woodrow Wilson had endured four years in office during which time the Republicans had begun to fight back.

The bookies initially stuck with Hughes, a serving Supreme Court justice who appeared to be a steady choice for centralists. 

But as the campaign wore on the NY exchanges began to slash their price on the favourite, and eventually by election night they were head-to-head.

Wilson eventually won out but lost the backing of 10 states. Remarkably, it was the only US election in 15 between 1884 and 1940 that the bookies got wrong.