assistant: There is no surefire way to prevent a democratically elected official from using their power to undermine the democratic system.  Some broad measures that can be taken to make a democracy or representative republic more robust against malicious politicians may include:

Forming an Independent Judiciary: Establishing an independent judiciary with the power to enforce the rule of law can prevent elected officials from abusing their power. This means that judges should be appointed based on merit and not political loyalty.

Separation of Powers: A system of checks and balances is necessary to prevent the concentration of power in one branch of government. Each branch should have specific powers and responsibilities that are clearly defined by the constitution.

Freedom of the Press: Freedom of the press is essential for a healthy democracy. An independent media can hold elected officials accountable for their actions, expose corruption and report on issues that affect the public interest.

Transparency and Accountability: Elected officials must be held accountable for their actions. This can be achieved through transparency in government operations, access to information, and strict rules on financial disclosures.

Anti-Corruption Measures: Corruption is a significant threat to democracy. Measures such as strict laws against bribery and embezzlement, whistleblower protection, and enforcement of ethics laws can prevent elected officials from using their power for personal gain.

Education and Civic Engagement: Educating citizens about the democratic process and encouraging civic engagement can strengthen democratic institutions. An informed and engaged citizenry is more likely to hold elected officials accountable and participate in the democratic process.

Term Limits: Establishing term limits for elected officials can prevent the concentration of power and reduce the risk of corruption. Term limits ensure that no single individual can hold office for an extended period, which can help prevent the establishment of a political dynasty.

assistant: It is quite rare for people to willingly hand their democratic government to an authoritarian dictator. One example of this happening is in Myanmar, which had a democratically-elected government until a military coup took place in February 2021. In the aftermath of the coup, civilian leader Aung San Suu Kyi and other government officials were detained and the military assumed control of the government. Since then, the military has imposed a range of authoritarian measures, including restrictions on freedom of speech and assembly.

prompter: If there was a military coup, it doesn't sound like Myanmar elected their authoritarian regime. I'm looking for examples where democratic countries elected a dictator who then refused to leave power. Like Belarus with Lukashenko.

assistant: Sure. I'll list some recent democratically elected dictators in order. However, it may be harder to determine if more recent dictators are actually a dictators or if only their opposition is claiming that.
* "Elected" 2014-Present: President Abdel Fattah el-Sisi -- Egypt
  * Sisi was appointed Minister of Defense by President Mohomad Morsi in 2012, and was then involved in the military coup that removed Morsi from office in 2013, before running for president in 2014.
* Elected 2010-present: Prime Minister Viktor Orbán -- Hungary
  * In 2006, an audio recording surfaced from a Hungarian socilaist party meeting where the then Prime Minister, Ferenc Gyurcsány, gave an obscenity-laden speech, which led to mass protests. Orbán announced plans to stage demonstrations across Hungary on the anniversy of the Soviet suppression of the 1956 revolution. But the revolutions petered out. In 2010, he won the election, and afterwards there were complaints of "free but not fair" elections due to gerrymandering and "other tweaks". According to Andre Marantaz, he slowly passed laws, amended the constitution, and wrote a new one allowing him to do whatever he wanted. He also "debilitated, delegitimatized, [and] hollowed out" courts and universities, as well as took over public media.
* Elected 2007-present: President Daniel Ortega -- Nicaragua
  * He was the leader of Nicaragua from 1979 to 1990, then failed in the 1996 and 2001 elections, but won the 2006 election. He then made alliances with other socialists like Hugo Chávez. His second administration became increasingly anti-democratic, and multiple organizations reported violent oppresion against protesters in the 2018-2022 Nicaraguan protests, after which there were waves of emmigration to Costa Rica, with over 30,000 Nicaraguans filing for asylum. He als ordered the closing of several NGOs, universities, and newspapers, and jailed many potential opponents in the 2021 election.

assistant: One example is Venezuela, where Hugo Chávez was democratically elected as president in 1998 and then re-elected in 2000. However, during his time in power, he consolidated power, restricted press freedom, and suppressed opposition. When he died in 2013, his hand-picked successor Nicolás Maduro took over, and he has continued to use authoritarian tactics to maintain his grip on power, including rigging elections, suppressing dissent, and using violence against protesters. Another example is Turkey, where President Recep Tayyip Erdogan has gradually eroded democratic institutions and cracked down on opposition since he was first elected in 2002. Despite facing significant protests and criticism from the international community, he has remained in power and consolidated control over the country.