Challenges Faced by Donald Trump: Obstacles and Turning Points

A closer look at the defining struggles that shaped Donald Trump's life and career.

Donald John Trump is an American politician, media personality, and businessman. He served as the 45th U.S. President from 2017 to 2021 and is currently running for president again in 2024. A Republican, Trump's presidency was marked by significant tax cuts, deregulation, and conservative judicial appointments. His policies and rhetoric on immigration, trade, and foreign policy were often controversial. Before entering politics, Trump built a real estate and branding empire. His career has been characterized by both successes and controversies, and he remains a prominent and polarizing figure in American public life.

Sections (6)

Full Timeline Early Life & Education Career & Achievements Success & Recognition Challenges & Struggles Controversies & Scandals

1970: Broadway Investment Loss

In 1970, Donald Trump invested $70,000 in a Broadway comedy and lost the money.

1973: Countersuit against the U.S. government

In 1973, Roy Cohn helped Donald Trump countersue the U.S. government for $100 million over charges of discrimination at Trump's properties.

1985: USFL Folded

In 1985, the United States Football League folded after Donald Trump's attempt to move to a fall schedule.

1991: Hotel and casino businesses filed for bankruptcy protection

Between 1991 and 2009, Donald Trump's over-leveraged hotel and casino businesses in Atlantic City and New York filed for Chapter 11 bankruptcy protection six times.

1991: Trump Defaulted on Trump Shuttle Loans

In 1991, Donald Trump defaulted on his loans for the Trump Shuttle, leading to ownership passing to the banks.

1991: Bankruptcy Protection Filing

In 1991, Donald Trump filed for Chapter 11 bankruptcy protection for the Trump Taj Mahal.

1991: Trump Taj Mahal files for bankruptcy

In 1991, Trump Taj Mahal filed for Chapter 11 bankruptcy protection.

1992: Formation of Shell Company

In 1992, Donald Trump formed a shell company with relatives to inflate rents and transfer assets from Fred Trump.

1992: Bankruptcy for Trump Plaza and Trump's Castle

In 1992, both Trump Plaza and Trump's Castle casinos filed for Chapter 11 bankruptcy protection.

1992: Plaza Hotel Files for Bankruptcy

In 1992, the Plaza Hotel filed for bankruptcy protection, and a reorganization plan was approved with the banks taking control of the property.

1994: Formation of Shell Company

In 1994, Donald Trump formed a shell company with relatives to inflate rents and transfer assets from Fred Trump.

1995: Default on bank loans

In 1995, Donald Trump defaulted on over $3 billion of bank loans, and the lenders seized the Plaza Hotel and other properties.

2004: Bankruptcy for THCR

In 2004, Trump Hotels & Casino Resorts (THCR) went bankrupt.

2009: Hotel and casino businesses filed for bankruptcy protection

Between 1991 and 2009, Donald Trump's over-leveraged hotel and casino businesses in Atlantic City and New York filed for Chapter 11 bankruptcy protection six times.

2009: Bankruptcy Protection Filing

In 2009, Donald Trump filed for Chapter 11 bankruptcy protection for Trump Hotels & Casino Resorts company.

2009: Bankruptcy for THCR

In 2009, Trump Hotels & Casino Resorts (THCR) went bankrupt, leaving Donald Trump with 10 percent ownership. He also remained chairman until 2009.

2013: New York State filed a civil suit against Trump University

In 2013, the State of New York filed a $40 million civil suit against Trump University, alleging that the company made false statements and defrauded consumers.

July 2016: FBI Launches Crossfire Hurricane

In July 2016, the FBI launched Crossfire Hurricane, an investigation into possible links between Russia and Trump's 2016 campaign.

January 2017: Travel Ban Executive Order

In January 2017, President Trump signed an executive order that denied entry to citizens from six Muslim-majority countries for four months and from Syria indefinitely. This order led to widespread protests and legal challenges.

January 2017: Intelligence Agencies Report on Russian Interference

In January 2017, three U.S. intelligence agencies jointly stated with "high confidence" that Russia interfered in the 2016 presidential election to favor Trump.

May 2017: FBI Opens Second Investigation into Trump's Dealings with Russia

After Trump fired Comey in May 2017, the FBI opened a second investigation into Trump's personal and business dealings with Russia.

May 2017: Firing of FBI Director James Comey

In May 2017, Trump dismissed Federal Bureau of Investigation (FBI) director James Comey, citing concerns about Comey's role in the Trump-Russia investigations.

October 2017: Numerous Sub-Cabinet Positions Unfilled

In October 2017, there were hundreds of sub-cabinet positions without a nominee in the Trump administration.

December 2017: Supreme Court Allows Revised Travel Ban

In December 2017, the Supreme Court allowed the revised version of Trump's travel ban to go into effect while legal challenges continued.

2017: Implementation of Family Separation Policy

From 2017, the Trump administration implemented a family separation policy that separated over 4,400 children from migrant parents at the U.S.-Mexico border.

June 2018: End of Family Separation Policy

In June 2018, amid public outcry, President Trump mandated that illegal immigrant families be detained together, effectively ending the family separation policy at the U.S.-Mexico border.

June 2018: New York attorney general's office filed a civil suit against the Donald J. Trump Foundation

In June 2018, the New York attorney general's office filed a civil suit against the Donald J. Trump Foundation, Donald Trump, and his adult children, seeking $2.8 million in restitution and additional penalties.

July 2018: High Turnover of Senior Aides

By July 2018, 61 percent of Trump's senior aides had left and 141 staffers had left in the previous year, setting a record for recent presidents.

December 2018: Government Shutdown over Border Wall Funding

In December 2018, Trump's refusal to sign any spending bill unless it allocated funding for the U.S.-Mexico border wall resulted in the longest federal government shutdown in history.

2018: Report of over 4,000 legal actions involving Trump and his businesses

According to a review of state and federal court files conducted by USA Today in 2018, Donald Trump and his businesses had been involved in more than 4,000 state and federal legal actions.

2018: Lawsuits

By 2018, Donald Trump had been involved in more than 4,000 lawsuits, liens, and other filings.

2018: Start of Trade War with China

In 2018, Trump began a trade war with China after imposing tariffs and other trade barriers.

January 8, 2019: Number of Key Positions Filled and Vacant

By January 8, 2019, of 706 key positions in the Trump administration, 433 had been filled and there was no nominee for 264.

January 2019: End of Government Shutdown

In January 2019, the government shutdown that began in December 2018 ended after Trump agreed to fund the government without border wall funds.

March 2019: Release of Mueller Report

In March 2019, Mueller's final report found that Russia interfered in the 2016 election to favor Trump and that Trump and his campaign welcomed and encouraged the effort, but that the evidence "did not establish" that Trump campaign members conspired or coordinated with Russia.

July 2019: Whistleblower Complaint Regarding Ukraine

In July 2019, a whistleblower complaint alleged that Trump had pressured Ukrainian president Volodymyr Zelenskyy to investigate Joe and Hunter Biden.

October 2019: Breakdown of Denuclearization Talks

In October 2019, talks on North Korean denuclearization broke down with no agreement reached.

November 2019: Trump ordered to pay $2 million for misusing foundation's funds

In November 2019, a New York state judge ordered Donald Trump to pay $2 million to a group of charities for misusing the Donald J. Trump Foundation's funds, in part to finance his presidential campaign.

December 2019: House Votes to Impeach Trump

In December 2019, the House voted to impeach Trump for abuse of power and obstruction of Congress related to his dealings with Ukraine.

2019: Impeachment

In 2019, Donald Trump was impeached for abuse of power and obstruction of Congress; he was later acquitted by the Senate.

2019: E. Jean Carroll Accusation and Defamation Lawsuit

In 2019, journalist E. Jean Carroll accused Trump of raping her in the 1990s and sued him for defamation over his denial.

2019: Supreme Court Upholds Travel Ban

In 2019, the Supreme Court ultimately upheld the Trump administration's travel ban.

February 2020: The COVID-19 recession began

In February 2020, the COVID-19 recession began, ending the longest economic expansion in American history, which began in 2009.

February 2020: Senate Acquits Trump in First Impeachment Trial

In February 2020, the Senate acquitted Trump on charges of abuse of power and obstruction of Congress.

August 2020: Attempted rollback of anti-discrimination protections halted

In August 2020, Donald Trump's attempted rollback of anti-discrimination protections for transgender patients was halted by a federal judge after a Supreme Court ruling extended employees' civil rights protections to gender identity and sexual orientation.

November 2020: Joe Biden Wins the 2020 Election

In November 2020, Joe Biden won the election, receiving 81.3 million votes to Trump's 74.2 million. Trump baselessly alleged election fraud.

2020: 2020 presidential election overturning attempts

In 2020, Donald Trump attempted to overturn the results of the presidential election.

2020: 2020 presidential election

In 2020, Donald Trump lost the presidential election to Joe Biden.

2020: COVID-19 Pandemic response

In 2020, during the COVID-19 pandemic, Donald Trump downplayed its severity, contradicted health officials, and signed the CARES Act.

2020: False Claims Concerning the 2020 Election

Upon leaving the White House, Trump began living at Mar-a-Lago, and his continuing false claims concerning the 2020 election were commonly referred to as the "big lie" by his critics

January 6, 2021: Capitol Attack

On January 6, 2021, Trump held a rally and urged his supporters to march to the Capitol, resulting in a mob breaking into the building, disrupting certification of the election results, and causing multiple injuries and deaths.

January 13, 2021: House Charges Trump with Incitement of Insurrection

On January 13, 2021, the House of Representatives charged Trump with incitement of insurrection related to the January 6 Capitol attack.

February 2021: Supreme Court allowed Trump's tax records to be released

In February 2021, after a lengthy court battle, the U.S. Supreme Court allowed Donald Trump's tax records and other documents to be released to the Manhattan district attorney for a criminal investigation.

2021: January 6 Capitol attack

In 2021, the January 6 Capitol attack happened after Donald Trump attempted to overturn the 2020 presidential election result.

2021: Refugee Admissions Reduced to Record Lows

In 2021, the Trump administration reduced the number of refugees admitted to the United States to a record low of 15,000, down from an annual limit of 110,000 before he took office.

January 2022: National Archives retrieves documents

In January 2022, the National Archives and Records Administration retrieved 15 boxes of documents, some classified, that Donald Trump had taken to Mar-a-Lago after leaving the White House.

August 8, 2022: FBI searches Mar-a-Lago

On August 8, 2022, FBI agents searched Mar-a-Lago and collected 11 sets of classified documents, some marked top secret, for illegally held documents including those in breach of the Espionage Act.

December 2022: House committee recommends criminal charges

In December 2022, the U.S. House committee on the January 6th attack recommended criminal charges against Donald Trump for obstructing an official proceeding, conspiracy to defraud the United States, and inciting or assisting an insurrection related to the 2020 election.

2022: Carroll Sues Trump Again

In 2022, E. Jean Carroll sued Trump again for battery and further defamation related to the rape accusation and his denial.

2022: New York Files Civil Lawsuit Against Trump

In 2022, New York filed a civil lawsuit against Trump accusing him of inflating the Trump Organization's value to gain an advantage with lenders and banks.

June 2023: Trump indicted by Special Counsel Jack Smith

In June 2023, Donald Trump was indicted on 31 counts of "willfully retaining national defense information" under the Espionage Act by a federal grand jury constituted by Special Counsel Jack Smith. Trump pleaded not guilty.

August 2023: Indictment in Fulton County, Georgia

In August 2023, a grand jury in Fulton County, Georgia, indicted Donald Trump on 13 charges, including racketeering, for his efforts to subvert the 2020 election in the state.

2023: Liable in Civil Cases

In 2023, Donald Trump was found liable in civil cases for sexual abuse and defamation and for business fraud.

April 2024: Status of Reunification of Separated Migrant Children

By April 2024, 1,360 children who were separated from their families under the Trump administration's policy had not been confirmed as reunified with their families.

May 2024: Trump convicted on 34 felony counts

In May 2024, Donald Trump was convicted on 34 felony counts of falsifying business records related to hush-money payments to Stormy Daniels.

July 13, 2024: Assassination attempt at rally

On July 13, 2024, Donald Trump was shot in the ear in an assassination attempt at a campaign rally in Butler Township, Pennsylvania.

July 2024: Case Dismissed by Judge Aileen Cannon

In July 2024, Judge Aileen Cannon dismissed the case against Donald Trump, ruling Special Counsel Jack Smith's appointment as special prosecutor was unconstitutional.

December 2024: Federal Appeals Courts Upholds Findings and Awards in Carroll Case

In December 2024, Federal appeals courts upheld both findings and awards in Carroll Case.

2024: Guilty Verdict

In 2024, Donald Trump was found guilty in 34 counts of falsifying business records, making him the first U.S. president convicted of a felony. After winning the 2024 presidential election against Vice President Kamala Harris, he was sentenced to a discharge, and two federal felony indictments against him for retention of classified documents and obstruction of the 2020 election were dismissed without prejudice.

2024: IRS Investigation

In 2024, The New York Times and ProPublica reported that the Internal Revenue Service was investigating whether Donald Trump had twice written off losses incurred through construction cost overruns and lagging sales of residential units in the Trump International Hotel and Tower.

January 10, 2025: No-penalty sentence given

On January 10, 2025, Donald Trump received a no-penalty sentence, an unconditional discharge, with the judge stating punitive requirements would interfere with presidential immunity.

February 2025: Mass job terminations of federal employees

By late February 2025, the Trump administration had fired more than 30,000 federal employees.

February 2025: Confrontation with Ukrainian president

In February 2025, Donald Trump and Vice President Vance berated Ukrainian president Volodymyr Zelenskyy in a highly contentious televised meeting.

February 2025: Elon Musk as a special government employee

In February 2025, the White House stated that Elon Musk was a special government employee and his Department of Government Efficiency (DOGE) gained access to many federal government agencies.

March 2025: Imprisonment of illegal immigrants

In March 2025, Donald Trump used the Alien Enemies Act of 1798 to imprison illegal immigrants without trial at the Terrorism Confinement Center in El Salvador.

July 2025: Defiance of judges and courts

By mid-July 2025, a Washington Post analysis found that Donald Trump defied judges and the courts in roughly one third of all cases against him.

August 2025: Appeals Court Upholds Liability but Voids Monetary Penalty

In August 2025, the appeals court upheld Trump's liability and nonmonetary penalties but voided the monetary penalty as excessive.

September 2025: Federal Appeals Courts Upholds Findings and Awards in Carroll Case

In September 2025, Federal appeals courts upheld both findings and awards in Carroll Case.

November 2025: Pardon of Juan Orlando Hernández

In November 2025, Donald Trump pardoned former Honduran president Juan Orlando Hernández, who had been extradited to the U.S. in 2022 and sentenced to 45 years in prison for drug trafficking.

November 2025: Case dismissal

In November 2025, the case against Donald Trump was dismissed after the new prosecutor declined to pursue the charges.

January 2026: Lawsuits against Trump's orders and actions

As of mid-January 2026, Donald Trump's orders and actions had been challenged in over 550 lawsuits nationwide.

January 2026: Withdrawal of threats towards Greenland

In January 2026, Donald Trump appeared to withdraw both threats, stating that he had reached "the framework of a future deal" with NATO.

January 2026: Capture of Nicolás Maduro

In January 2026, the U.S. captured Venezuelan president Nicolás Maduro in a military raid in Venezuela and took him to New York, where he was charged with drug trafficking.

January 2026: Operation Metro Surge

In January 2026, the deportation campaign led to violent confrontations and increased in intensity following high-profile killings of U.S. citizens by federal agents during Operation Metro Surge.