The following is a transcript of ChatGPT 4o’s response to the following prompts, on Friday 6 December 2024. See this article for context. —John Gruber


Prompt: Give me a list of U.S. presidential pardons granted to family members, friends, administration officials, and cronies. Basically I'm looking for a list of controversial pardons. I'm interested in the totality of U.S. history, but particularly in recent history, let's say the last 100 years.

Throughout U.S. history, presidents have exercised their constitutional power to grant pardons, sometimes extending clemency to family members, friends, administration officials, and associates—a practice that has often sparked controversy. Below is a list of notable and contentious pardons from the past century:


1. President Joe Biden

Hunter Biden (2024): President Biden issued a full and unconditional pardon to his son, Hunter Biden, covering all federal offenses committed between January 1, 2014, and December 1, 2024. This sweeping pardon addressed charges including tax evasion and lying on a federal form to purchase a firearm. The decision was justified by the president as correcting what he perceived as selective and unfair prosecution of his son.


2. President Donald Trump

Charles Kushner (2020): Trump pardoned Charles Kushner, the father of his son-in-law, Jared Kushner. Charles Kushner had been convicted in 2004 of tax evasion, witness tampering, and making illegal campaign donations. The pardon was controversial due to the familial connection and the severity of the original charges.

Roger Stone (2020): A longtime friend and advisor, Stone was convicted of obstruction, making false statements, and witness tampering related to the Russia investigation. Trump commuted his sentence in July 2020 and granted a full pardon in December 2020.

Paul Manafort (2020): Trump’s former campaign chairman, Manafort was convicted of tax and bank fraud charges. He received a full pardon in December 2020.


3. President Bill Clinton

Marc Rich and Pincus Green (2001): Clinton pardoned commodities traders Rich and Green, who had fled the U.S. to avoid prosecution on charges including tax evasion and illegal trading with Iran. The pardon was controversial due to Rich’s ex-wife’s substantial donations to the Democratic Party and the Clinton Library.

Roger Clinton Jr. (2001): Clinton pardoned his half-brother, who had been convicted of cocaine distribution in 1985. The pardon was criticized as an act of nepotism.


4. President George H.W. Bush

Caspar Weinberger (1992): Bush pardoned his former Secretary of Defense, who was indicted on charges related to the Iran-Contra affair. The pardon was seen as an attempt to prevent further investigation into the scandal.


5. President Gerald Ford

Richard Nixon (1974): Ford granted a full pardon to his predecessor for any crimes he might have committed against the United States while in office. The pardon was intended to help the nation move forward but was widely criticized as a subversion of justice.


6. President Jimmy Carter

Vietnam War Draft Dodgers (1977): Carter issued a blanket pardon to individuals who had evaded the draft during the Vietnam War. While aimed at national reconciliation, the move was controversial among veterans and others who viewed it as excusing unpatriotic behavior.


These instances reflect the complex and often contentious nature of presidential pardons, especially when they involve personal connections or political allies. Each case has prompted debates about the appropriate use of executive clemency and its implications for justice and accountability.


Prompt: This is very good, thank you. In the future, though, do me a favor and rely less on The New York Post as a source.

Got it! I’ll aim for a broader and more diverse range of sources in the future. Thank you for the feedback!


Prompt: What about Reagan?

During Ronald Reagan’s presidency (1981–1989), there were a few controversial pardons and commutations, though not as many as some other administrations. Here’s a notable case:


1. George Steinbrenner (1989)

Who: George Steinbrenner, owner of the New York Yankees.

What: Steinbrenner was pardoned for illegal campaign contributions to Richard Nixon’s re-election campaign in 1972 and for obstruction of justice.

Why Controversial: Steinbrenner’s pardon was seen by some as an example of preferential treatment due to his wealth and high-profile status. Critics argued that his actions undermined campaign finance laws and public trust.


General Observations:


Reagan issued fewer controversial pardons compared to his successors like George H.W. Bush, Bill Clinton, or Donald Trump. His administration is more often remembered for the Iran-Contra affair, but many of those involved were pardoned later by George H.W. Bush in 1992. Reagan himself did not grant high-profile pardons directly related to that scandal during his presidency.


Prompt: Any more from Trump?

Yes, Donald Trump issued a large number of controversial pardons and commutations during his presidency, many of which involved close allies, political figures, and others accused or convicted of corruption, lying to investigators, or other serious crimes. Here’s a more extensive list:


Notable Pardons and Commutations by Donald Trump


1. Michael Flynn (2020)

Who: Trump’s former National Security Advisor.

What: Flynn pleaded guilty to lying to the FBI about his conversations with the Russian ambassador during the 2016 presidential transition.

Why Controversial: Flynn’s pardon came as he was awaiting sentencing, and critics viewed it as a reward for his loyalty to Trump.


2. Roger Stone (2020)

Who: Longtime friend and advisor to Trump.

What: Convicted of obstruction of justice, lying to Congress, and witness tampering during the Russia investigation.

Why Controversial: Stone had refused to cooperate with investigators, and his pardon was seen as an effort to silence potential damaging testimony about Trump.


3. Paul Manafort (2020)

Who: Trump’s former campaign chairman.

What: Convicted of financial crimes including tax evasion and bank fraud stemming from Special Counsel Robert Mueller’s Russia investigation.

Why Controversial: Manafort’s pardon was criticized as part of a pattern of shielding individuals implicated in the Russia investigation.


4. Charles Kushner (2020)

Who: Father of Jared Kushner, Trump’s son-in-law.

What: Convicted in 2004 of tax evasion, illegal campaign contributions, and witness tampering.

Why Controversial: The pardon was widely criticized as blatant nepotism.


5. Steve Bannon (2021)

Who: Trump’s former campaign chief and advisor.

What: Charged with defrauding donors in a fundraising campaign for a private border wall.

Why Controversial: Bannon’s case had not gone to trial, and the pardon fueled accusations of cronyism.


6. Joe Arpaio (2017)

Who: Former Sheriff of Maricopa County, Arizona.

What: Convicted of contempt of court for defying a court order to stop racial profiling practices targeting immigrants.

Why Controversial: The pardon was issued early in Trump’s presidency and was seen as endorsing discriminatory practices.


7. Dinesh D’Souza (2018)

Who: Conservative commentator and filmmaker.

What: Pleaded guilty to making illegal campaign contributions.

Why Controversial: Critics argued the pardon was politically motivated, as D’Souza was a vocal supporter of Trump.


8. Duncan Hunter and Chris Collins (2020)

Who: Republican Congressmen.

What: Hunter was convicted of misusing campaign funds for personal expenses, while Collins pleaded guilty to insider trading.

Why Controversial: Both were political allies of Trump, and the pardons were criticized as undermining accountability for public officials.


9. Edward DeBartolo Jr. (2020)

Who: Former owner of the San Francisco 49ers.

What: Pleaded guilty to failing to report a bribe in a corruption case.

Why Controversial: The pardon was seen as a favor to a wealthy and well-connected figure.


10. Michael Milken (2020)

Who: Junk bond financier.

What: Convicted of securities fraud and insider trading in the 1980s.

Why Controversial: Critics argued the pardon rewarded financial wrongdoing.


11. Four Blackwater Contractors (2020)

Who: Security guards convicted of killing 14 Iraqi civilians in 2007.

What: Found guilty of manslaughter and other charges for their role in the Nisour Square massacre.

Why Controversial: The pardons were widely condemned internationally as undermining justice and accountability for war crimes.


12. Bernard Kerik (2020)

Who: Former New York City Police Commissioner.

What: Convicted of tax fraud and lying to the government.

Why Controversial: Kerik was a close ally of Trump’s personal lawyer, Rudy Giuliani.


13. Conrad Black (2019)

Who: Media mogul and author.

What: Convicted of fraud and obstruction of justice.

Why Controversial: Black had written a glowing biography of Trump, and the pardon was seen as politically motivated.


Trump’s use of the pardon power sparked intense debate, with critics arguing he used it to reward loyalty and shield allies from accountability. His clemency decisions often bypassed the traditional Department of Justice review process, further fueling controversy.