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. A Republican, Trump's presidency was marked by significant policy changes, including tax cuts and deregulation. Before entering politics, he built a real estate and branding empire. He is currently running for president again in 2024.

Sections (6)

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

1970: Investment in Broadway Comedy

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

1973: Countersuit Against the U.S. Government

In 1973, with Roy Cohn's help, Donald Trump countersued the U.S. government for $100 million over charges of discrimination in his properties.

1985: League Folded After 1985 Season

The United States Football League folded after the 1985 season, largely due to Donald Trump's actions.

1991: Default on Trump Shuttle loans

In 1991, Donald Trump defaulted on his loans for Trump Shuttle, which he had purchased in 1988, and ownership of the airline passed to the banks.

1991: Bankruptcy Filing for Trump Taj Mahal

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

1991: First bankruptcy protection filing

In 1991, Donald Trump's over-leveraged hotel and casino businesses in Atlantic City and New York filed for Chapter 11 bankruptcy protection for the first time.

1992: Shell Company Formation

In 1992, Donald Trump and relatives formed a shell company to pay vendors for his rental units and inflate costs for rent increases.

1992: Bankruptcy Filing for Trump's Castle

In 1992, Trump's Castle filed for Chapter 11 bankruptcy protection.

1992: Plaza Hotel Bankruptcy

In 1992, the Plaza Hotel filed for bankruptcy protection, leading to banks taking control of the property.

1994: Continuation of Shell Company Scheme

In 1994, Donald Trump continued using the shell company scheme to inflate rents and transfer assets from Fred Trump.

1995: Declared a $916 million loss

In 1995, Donald Trump declared a loss of $916 million. This loss was revealed when portions of Trump's state filings were leaked in October 2016.

1995: Default on Bank Loans

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

2004: Bankruptcy of Trump Hotels & Casino Resorts

In 2004, Trump Hotels & Casino Resorts (THCR) went bankrupt, leaving Donald Trump with 10 percent ownership.

2009: Sixth bankruptcy protection filing

In 2009, Donald Trump's over-leveraged hotel and casino businesses in Atlantic City and New York filed for Chapter 11 bankruptcy protection for the sixth time between 1991 and 2009.

2009: Bankruptcy Filing for Trump Hotels & Casino Resorts

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

2010: Name change to Trump Entrepreneur Initiative

In 2010, Trump University changed its name to the Trump Entrepreneur Initiative after New York State authorities said that its use of "university" violated state law.

2013: New York filed suit against Trump University

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

2014: Weakened Sanctions after Crimea Annexation

In 2014, Donald Trump weakened the toughest U.S. sanctions imposed after the Russian annexation of Crimea.

July 2016: FBI Launches Crossfire Hurricane Investigation

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

October 2016: Leak of 1995 tax filings

In October 2016, portions of Donald Trump's state filings for 1995 were leaked, revealing he declared a $916 million loss that year, potentially allowing him to avoid taxes for up to 18 years.

2016: Settlement of Trump University cases

Shortly after winning the 2016 presidential election, Donald Trump agreed to pay a total of $25 million to settle three cases related to Trump University.

January 2017: Executive Order on Travel Ban

In January 2017, Donald Trump signed an executive order denying entry to citizens from six Muslim-majority countries for four months and from Syria indefinitely, leading to protests and legal challenges.

January 2017: U.S. 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 Donald Trump.

May 2017: Dismissal of FBI Director James Comey

In May 2017, Donald Trump dismissed Federal Bureau of Investigation (FBI) director James Comey.

May 2017: FBI Opens Second Investigation After Comey Firing

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

October 2017: Hundreds of Sub-Cabinet Positions Unfilled

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

December 2017: Supreme Court Allows Revised Travel Ban to Take Effect

In December 2017, the Supreme Court allowed a revised version of Donald Trump's travel ban to go into effect.

2017: Trump Administration Initiates Family Separation Policy

From 2017 to 2018, the Trump administration implemented a policy of family separation at the U.S.-Mexico border, separating over 4,400 children from their migrant parents.

2017: Americans Doubt Trump's Religious Beliefs

In 2017, during Donald Trump's first presidency (2017-2021), a survey indicated that 63% of Americans did not believe that he was religious despite his claims of Christian affiliation.

June 2018: Trump Mandates Detainment of Illegal Immigrant Families Together

In June 2018, amidst public outrage, Donald Trump mandated that illegal immigrant families be detained together unless there was a risk for the child, following the family separation policy.

June 2018: Civil suit filed against 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 Donald Trump's senior aides had left their positions, setting a record for recent presidents.

December 2018: Government Shutdown Due to Border Wall Funding Dispute

In December 2018, Donald Trump's refusal to sign a spending bill unless it included funding for the border wall resulted in a federal government shutdown.

2018: Involvement in legal actions

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

2018: Lawsuits and Filings

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

2018: Start of Trade War with China

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

January 8, 2019: Many Key Positions Unfilled

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: Government Shutdown Ends Without Wall Funding

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

March 2019: Mueller Report Findings

In March 2019, the Mueller report found that Russia interfered in the 2016 election to favor Donald Trump and that Trump's campaign welcomed the effort, but the evidence "did not establish" a conspiracy.

July 2019: Whistleblower Complaint Regarding Ukraine

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

October 2019: Talks on North Korean Denuclearization Break Down

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

November 2019: Trump ordered to pay charities

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.

December 2019: House Votes to Impeach Trump

In December 2019, the House of Representatives voted to impeach Donald Trump for abuse of power and obstruction of Congress.

2019: Federal budget deficit increased

By 2019, under Donald Trump, the federal budget deficit increased by almost 50 percent, reaching nearly $1 trillion.

2019: First Impeachment

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

2019: Supreme Court Upholds Travel Ban

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

February 2020: Start of COVID-19 recession

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

February 2020: Senate Acquits Trump

In February 2020, the Senate acquitted Donald Trump on the impeachment charges.

August 2020: Attempted rollback of anti-discrimination protections

In August 2020, Donald Trump's attempted rollback of anti-discrimination protections for transgender patients was halted by a federal judge.

November 2020: Joe Biden Wins the 2020 Election

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

2020: COVID-19 Pandemic Response and Election Loss

In 2020, during the COVID-19 pandemic, Donald Trump downplayed its severity, contradicted health officials, and signed the CARES Act. He also lost the 2020 presidential election to Joe Biden.

January 6, 2021: Capitol Attack

On January 6, 2021, Donald Trump held a rally and urged his supporters to march to the Capitol, resulting in a mob breaking into the building.

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

On January 13, 2021, the House charged Donald Trump with incitement of insurrection following the January 6 Capitol attack.

February 2021: Release of tax records allowed

In February 2021, the U.S. Supreme Court allowed Donald Trump's tax records to be released to the Manhattan district attorney for a criminal investigation.

May 2021: Adoption of "Big Lie" Terminology

In May 2021, Donald Trump and many of his supporters began using the term "big lie" to refer to the 2020 election itself, continuing to push false claims of election fraud.

2021: Capitol Attack and Second Impeachment

In 2021, Donald Trump attempted to overturn the 2020 election results, culminating in the January 6 Capitol attack. He was impeached for incitement of insurrection but acquitted by the Senate.

2021: Refugee Admissions Reduced to Record Low

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

2023: Liable in Civil Cases

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

April 2024: Over 1,300 Children Not Confirmed Reunified with Families

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

May 2024: Guilty Verdict in Business Records Case

In May 2024, Donald Trump was found guilty on 34 counts of falsifying business records, making him the first U.S. president convicted of a felony.

July 13, 2024: Assassination attempt on Trump

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: Judge dismisses classified documents case

In July 2024, judge Aileen Cannon dismissed the case regarding Donald Trump's retention of classified documents, ruling that Special Counsel Jack Smith's appointment as special prosecutor was unconstitutional.

December 2024: Appeals court upholds ruling in E. Jean Carroll case

In December 2024, a federal appeals court upheld the finding that Donald Trump was liable for sexual abuse and defamation against E. Jean Carroll, as well as the monetary award.

2024: IRS Investigation

In 2024, The New York Times and ProPublica reported that the IRS was investigating whether Donald Trump had improperly written off losses from the Trump International Hotel and Tower in Chicago.

January 10, 2025: Trump receives no-penalty sentence in hush-money case

On January 10, 2025, the judge in Donald Trump's hush-money case gave him a no-penalty sentence, known as an unconditional discharge, stating that punitive requirements would interfere with presidential immunity.

March 2025: Trump uses Alien Enemies Act to deport migrants

In March 2025, Donald Trump used the Alien Enemies Act of 1798 to deport migrants without trial to be imprisoned 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, actions which were described by legal experts as unprecedented for any presidential administration.

August 2025: Appeals court upholds liability in Trump Organization case

In August 2025, the appeals court upheld Donald Trump's liability and nonmonetary penalties in the New York civil lawsuit accusing him of inflating the Trump Organization's value, but voided the monetary penalty as excessive.

September 2025: Appeals court upholds ruling in E. Jean Carroll case

In September 2025, a federal appeals court upheld the finding that Donald Trump was liable for sexual abuse and defamation against E. Jean Carroll, as well as the monetary award.

November 2025: Case dismissed in Fulton County, Georgia

In November 2025, the case in Fulton County, Georgia, where Donald Trump was indicted on 13 charges for his efforts to subvert the 2020 election, 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: Operation Metro Surge leads to confrontations

In January 2026, the aggressive and hardline deportation campaign led to large nationwide protests and violent confrontations with migrants and protesters which increased in intensity following high-profile killings of U.S. citizens by federal agents during Operation Metro Surge.