Chileans vote on December 14 in a presidential runoff between communist coalition leader Jeannette Jara and ultraconservative José Antonio Kast, with polls indicating the country will likely elect its most right-wing leader since the return to democracy in 1990.

Kast, 59, a former lawmaker and son of a Nazi party member who has openly expressed admiration for the Augusto Pinochet dictatorship, leads in opinion surveys despite finishing second in the first round with 23.9% compared to Jara's 26.6%. His advantage reflects a rightward shift amongst voters concerned about immigration and rising crime, analysts say.

The election marks Chile's most polarised presidential contest in decades, exposing fundamental divisions over how to address security concerns and migration whilst preserving social gains made under the current centre-left government of President Gabriel Boric.

Kast has centred his campaign on promises to create an "emergency government" to combat crime through maximum security prisons and tougher penalties, whilst vowing mass deportations of an estimated 337,000 undocumented migrants—mostly Venezuelans who arrived during the past seven years.

"We are going to close the borders in all those places where there are irregular crossings," Kast said during a debate on December 9.

Unlike his failed presidential bids in 2017 and 2021, when he lost to Boric, Kast has avoided discussing his ultraconservative views on abortion and same-sex marriage, focusing instead on security and immigration issues that have boosted right-wing candidates globally.

His economic platform, which has been broadly welcomed by investors, proposes $6bn in spending cuts over 18 months, though economists across the political spectrum have questioned whether such austerity is achievable without reducing social benefits. His economic team acknowledged to the Associated Press that a "longer period" for adjustments might be "preferable".

Jara, 51, leads the broadest progressive coalition in Chilean history, spanning from the Communist Party to centrist Christian Democrats. The former labour minister under Boric engineered significant welfare measures including a shorter workweek, higher minimum wage and improved pension system.

However, Jara faces the challenge of representing a government with 30% approval ratings whilst defending her Communist Party membership in a country where anti-communist sentiment remains strong.

"Just the name 'Communist Party' scares people," Lucía Dammert, a sociologist and Boric's first chief of staff, told AP.

Jara has sought to distance herself from the Boric administration, insisting she has a different "style" and is not "the continuity candidate". She announced before the first round that she would suspend or resign from the Communist Party if elected president. In a bid to convey a more moderate image, she has pledged to boost foreign investment and has criticised Venezuelan authoritarian President Nicolas Maduro.

Her platform includes a "vital income" of approximately $800 monthly for vulnerable families and lifting bank secrecy to combat organised crime.

Political analysts say Kast's victory would align Chile with a rightward trend across Latin America, following similar shifts in Argentina and Bolivia, whilst continuing a pattern where Chilean voters have rejected incumbent coalitions at every election since 2005.

"His style is very similar to that of the European populist radical right; he is much closer to Meloni in Italy or Le Pen in France," said Cristóbal Rovira of the Catholic University, as quoted by EFE.

If elected, Kast would become the first president since democracy's return in 1990 who actively campaigned for Pinochet's continuation during the 1988 plebiscite.