He has said Brazil´s military dictatorship (1964-1985) made a mistake by torturing people when it should have killed them, repeatedly referred to one of the worst torturers of the dictatorship as a "hero", and said police should have "carte blanche" to kill criminal suspects. "There's a light at the end of the tunnel".
Early in the evening, as thousands of his supporters celebrating outside his house in Rio de Janeiro's posh Barra de Tijuca neighborhood, Mr. Bolsonaro took to video streaming - his trademark channel - to thank voters, tout his "governability" and slam his media critics.
Meanwhile, polling revealed an increase in support for Jair Bolsonaro.
"I was never alone. For the first time I feel represented", said Andre Luiz Lobo, 38, a businessman who - not incidentally, given the accusations of racism against his candidate - is black. "It's a promise to God", he said, standing next to his wife and many cheering supporters. In the 2016 US elections, Trump often billed himself as the man who wasn't afraid to say what everyone else was thinking.
Polls for the run-off election opened at 8 a.m. local time (1100 UTC) for the country's 143 million voters to choose between the populist ex-army captain Jair Bolsonaro and his leftist challenger Fernando Haddad, a former mayor of Sao Paolo. We can not guarantee that it is suitable for the visually or hearing impaired.
The Supreme Electoral Tribunal says that with more than 94 percent of ballots counted, Bolsonaro leads with 55.5 percent of the vote to Haddad's 44.5 percent.
In the 2016 United States presidential election, Trump often billed himself as the man who wasn't afraid to say what everyone else was thinking.
In a Datafolha poll also released late Saturday, Bolsonaro had 55 percent of voter backing, compared with 45 percent for Haddad.
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He may have to do it one more time though as he is now in line to start Game 7 at Fenway Park, if the series makes it that far. Despite still holding the series lead, Boston will need to dig deep to prevent the feeling that things are slipping away.
Polls ahead of Sunday's vote showed Mr Bolsonaro with a 10-point advantage. Several Brazilian heavyweights came out against him, arguing that he was a direct risk to the world's fourth-largest democracy. Haddad has promised a continuation of many progressive policies of his Workers' Party, which governed from 2003 to 2016.
More than a dozen U.S. Democratic congressmen have written a letter urging Secretary of State Mike Pompeo to make clear that American aid to and co-operation with Brazil "is contingent on the upholding of basic human rights and democratic values by its leaders".
His inauguration will be on January 1, 2019.
As late as Sunday morning, Haddad was still holding out hope that he could win after several key endorsements late Saturday. Sao Paulo's benchmark Bovespa stock index .BVSP has risen 13.5 percent since mid September.
But he fell short of the 50 per cent needed to win outright and avoid a runoff against Haddad, from the Workers' Party. The Workers' Party founder, known simply as Lula, is serving a 12-year sentence for corruption.
The past few years in Brazil have been exceptionally turbulent.
For the presidency are fighting right-wing MP Air Bolsonaro and representative of the left Party workers Fernando Added. The economy suffered a two-year-long recession and is only beginning to emerge, with growth stagnant and unemployment high. And scores of politicians and executives have been jailed in the Carwash corruption investigation that uncovered a multi-billion-dollar scheme to trade public contracts and official favors for bribes and kickbacks. He also wants to let more Brazilians buy weapons to fight crime.
Many observers predicted that a newcomer would emerge to harness that anti-establishment anger.
Brazilians are voting Sunday-weighing their hunger for radical change against fears that the presidential front-runner could threaten democracy as they cast ballots after a bitter campaign that was frequently marred by violence.