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 member of the Republican Party, Trump is also known for his real estate development and branding ventures. He is a controversial figure known for his populist rhetoric, policies, and frequent use of social media.
1973: Countersuit Against U.S. Government
In 1973, Donald Trump countersued the U.S. government for $100 million over charges of racial discrimination at his properties.
1985: League Folded
In 1985, after the season ended, the United States Football League folded after Trump's attempt to merge with the NFL.
1991: Bankruptcy Protection Filing
In 1991, Donald Trump filed for Chapter 11 bankruptcy protection for his businesses.
1991: Bankruptcy Filing for Trump Taj Mahal
In 1991, Donald Trump filed for Chapter 11 bankruptcy protection for the Trump Taj Mahal.
1992: End of Trump Shuttle Operation
In 1992, Donald Trump ceased operating the Trump Shuttle after defaulting on his loans.
1992: Bankruptcy Filings for Trump Plaza and Trump Castle
In 1992, both Trump Plaza and Trump Castle casinos filed for Chapter 11 bankruptcy protection.
1992: Plaza Hotel Bankruptcy Filing
In 1992, the Plaza Hotel filed for bankruptcy protection.
1994: Sale of Interest in Riverside South
In 1994, struggling with debt, Donald Trump sold most of his interest in the Riverside South project to Asian investors.
1995: Default on Bank Loans and Seizure of Properties
In 1995, Donald Trump defaulted on over $3 billion of bank loans, leading to the seizure of the Plaza Hotel and other properties.
2004: THCR Bankruptcy
In 2004, Trump Hotels & Casino Resorts went bankrupt.
2009: Bankruptcy Protection Filing
In 2009, Donald Trump filed for Chapter 11 bankruptcy protection for his businesses.
2009: THCR Bankruptcy
In 2009, Trump Hotels & Casino Resorts went bankrupt. Donald Trump remained chairman until 2009.
2013: Civil Suit Against Trump University
In 2013, the State of New York filed a $40 million civil suit against Trump University, alleging false statements and consumer fraud.
June 2015: NBC and Univision Drop Pageants
In June 2015, NBC and Univision dropped the Miss Universe pageants in reaction to Donald Trump's comments about Mexican immigrants.
July 2016: FBI launched Crossfire Hurricane
In July 2016, the FBI initiated Crossfire Hurricane, an investigation into potential connections between Russia and Donald Trump's 2016 presidential campaign.
2016: Settlement of Trump University Lawsuits
In 2016, Donald Trump agreed to pay $25 million to settle lawsuits related to Trump University.
2016: Rigged Election Claims
In 2016, Trump mentioned 'rigged election' and 'election interference'.
2016: Affair Alleged
In 2016, during the election cycle, Trump allegedly had an affair with Stormy Daniels.
January 2017: Travel ban executive order
In January 2017, Trump signed an executive order temporarily denying entry to citizens from seven Muslim-majority countries. This action sparked widespread protests and legal challenges, leading to nationwide injunctions.
January 2017: Intelligence Agencies State Russia Favored Trump
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 Opened Second Investigation After Comey Firing
After Trump fired Comey in May 2017, the FBI commenced a second investigation into Trump's personal and business dealings with Russia.
October 2017: Hundreds of sub-cabinet positions without a nominee
In October 2017, there were hundreds of sub-cabinet positions within the Trump administration without a nominee. The slow pace of appointments raised concerns about the functioning of the executive branch.
June 2018: Reversed family separation policy
In June 2018, amidst public outcry, Trump reversed the administration's policy of separating migrant families at the U.S.-Mexico border. He mandated that families be detained together unless there were concerns about the child's safety.
July 2018: High turnover of senior aides
As of early July 2018, 61 percent of Trump's senior aides had left their positions, and 141 staffers had left in the previous year. These figures set a record for recent presidential administrations.
December 2018: Government shutdown over border wall funding
In December 2018, Trump's refusal to sign a spending bill without border wall funding led to the longest federal government shutdown in U.S. history, lasting 35 days. The shutdown highlighted the conflict between Trump's campaign promises and congressional opposition.
2018: Signed legislation to increase funding for drug treatments
In 2018, Trump signed legislation aimed at increasing funding for drug treatments in response to the opioid epidemic, but faced criticism for lacking a concrete strategy. The legislation was meant to combat the ongoing drug crisis.
2018: APSA Ranking
In 2018, members of the American Political Science Association (APSA) ranked Donald Trump as the worst president.
January 8, 2019: Key positions unfilled in the executive branch
By January 8, 2019, of 706 key positions in the executive branch, 433 had been filled, and there was no nominee for 264. The large number of unfilled positions hindered the administration's ability to implement its policies effectively.
January 2019: End of government shutdown without border wall funding
In January 2019, the 35-day government shutdown ended after Trump agreed to fund the government without securing funds for the border wall. The resolution marked a temporary setback for his administration's immigration policies.
February 2019: Second meeting with Kim Jong Un in Hanoi
In February 2019, Trump met with Kim Jong Un for a second time in Hanoi. The talks aimed to further negotiations on denuclearization but ultimately did not result in a comprehensive agreement.
March 2019: Mueller Report Finds Russian Interference
In March 2019, Mueller submitted his final report which found that Russia interfered in 2016 to favor Trump, and Trump's campaign welcomed this interference, but there was no established conspiracy.
April 2019: House Oversight Committee Issues Subpoenas
In April 2019, the House Oversight Committee issued subpoenas seeking financial details from Trump's banks and accounting firm. He sued to prevent the disclosures.
October 2019: Talks with North Korea broke down
In October 2019, talks between the U.S. and North Korea broke down, and no denuclearization agreement was reached. This setback highlighted the difficulties in achieving a lasting resolution to the North Korean nuclear issue.
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: First Impeachment
In 2019, Donald Trump was impeached for abuse of power and obstruction of Congress.
2019: E. Jean Carroll Accuses Trump of Rape
In 2019, journalist E. Jean Carroll accused Trump of raping her in the 1990s and sued him for defamation over his denial.
February 2020: Senate Acquits Trump in First Impeachment
In February 2020, the Senate acquitted Trump in his first impeachment trial.
July 2020: Handling of COVID-19 pandemic became a major issue
By July 2020, Trump's handling of the COVID-19 pandemic had become a major issue in the presidential election. His response to the crisis faced widespread criticism and affected public perception of his leadership.
August 2020: Attempted rollback of anti-discrimination protections
In August 2020, Trump's administration attempted to roll back anti-discrimination protections for transgender patients. However, a federal judge halted the rollback after a Supreme Court ruling extended civil rights protections to gender identity and sexual orientation.
October 2, 2020: Tested positive for COVID-19
On October 2, 2020, Trump tweeted that he had tested positive for COVID-19, part of a White House outbreak. His diagnosis highlighted the severity of the pandemic and raised concerns about his administration's handling of the crisis.
November 2020: Biden Wins 2020 Election
In November 2020, Joe Biden won the election, receiving 81.3 million votes to Trump's 74.2 million and 306 electoral votes to Trump's 232.
December 2020: Military on 'Red Alert' Over Trump's Actions
In December 2020, reports emerged that the U.S. military was on 'red alert', with concerns among ranking officers about Trump potentially declaring martial law or initiating military actions.
2020: Cases Dismissed
After his reelection, the 2020 election obstruction case and the classified documents case were dismissed without prejudice due to Justice Department policy against prosecuting sitting presidents.
2020: Trump's False Claims Concerning the Election
After leaving the White House, Trump's continuing false claims concerning the 2020 election were commonly referred to as the 'big lie'.
2020: Losing the 2020 presidential election
In 2020, Donald Trump lost the presidential election to Joe Biden and attempted to overturn the outcome.
2020: Rigged Election Claims
In 2020, Trump mentioned 'rigged election' and 'election interference'.
2020: Trump's Efforts to Overturn the Election
In 2020, Trump was involved in efforts to overturn the election and was later investigated for these activities and his involvement in the January 6 attack.
January 6, 2021: Trump Rally Precedes Capitol Attack
On January 6, 2021, Trump held a rally in Washington, D.C., calling for the election to be overturned and urging supporters to march to the Capitol, which resulted in an attack on the Capitol building.
January 13, 2021: House Charges Trump with Incitement of Insurrection
On January 13, 2021, the House charged Trump with incitement of insurrection following the January 6 attack.
May 2021: Trump Supporters Embrace Election Term
In May 2021, Donald Trump's supporters began to embrace the term 'big lie' to refer to the election itself.
2021: C-SPAN Presidential Historians Survey
In 2021, C-SPAN's survey of presidential historians ranked Donald Trump as the fourth-worst president based on leadership characteristics like moral authority and administrative skills.
2021: Second Impeachment
In 2021, Donald Trump was impeached for incitement of insurrection.
2021: January 6 Capitol Attack
In 2021, Trump's attempts to overturn the election culminated in the January 6 Capitol attack.
2021: Reduced number of refugees admitted 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. This action continued the administration's trend of restricting immigration and tightening border control policies.
January 2022: National Archives Retrieves Documents from Mar-a-Lago
In January 2022, the National Archives and Records Administration retrieved 15 boxes of documents, some classified, from Mar-a-Lago.
July 2022: Trump Pressures State Legislators to Overturn Election
As of July 2022, Trump continued to pressure state legislators to overturn the 2020 election.
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.
September 2022: Settlement Reached with Mazars USA
In September 2022, Trump and the House Oversight Committee reached a settlement regarding Mazars USA, and the firm began turning over documents.
December 2022: House Committee Recommends Criminal Charges
In December 2022, the U.S. House committee on the January 6 attack recommended criminal charges against Trump.
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.
2022: Siena College Research Institute Survey
In 2022, the Siena College Research Institute's survey ranked Donald Trump as the third-worst president, with low ratings in most categories.
March 2023: Campaign Diverts Funds to Leadership PAC
In March 2023, Trump's campaign began diverting 10 percent of donations to his leadership PAC.
June 2023: Trump Indicted on Espionage Act Charges
In June 2023, Trump was indicted on 31 counts of 'willfully retaining national defense information' under the Espionage Act.
August 2023: Trump Indicted in Georgia
In August 2023, Trump was indicted on 13 charges in Fulton County, Georgia, for his efforts to subvert the 2020 election in the state.
December 2023: Colorado Court Rules Trump Disqualified
In December 2023, the Colorado Supreme Court ruled Trump disqualified for the Colorado Republican primary.
2023: Held Liable in Civil Cases
In 2023, Donald Trump was held liable in civil cases for sexual abuse, defamation, and business fraud.
May 2024: Trump Convicted on 34 Felony Counts
In May 2024, Trump was convicted on 34 felony counts of falsifying business records related to hush-money payments.
July 13, 2024: Assassination Attempt on Trump
On July 13, 2024, Trump was shot in the ear in an assassination attempt at a campaign rally.
July 2024: Case Dismissed
In July 2024, a judge dismissed the Espionage Act case against Trump, ruling that the special prosecutor's appointment was unconstitutional.
2024: Convicted of Falsifying Business Records
In 2024, Donald Trump was found guilty of falsifying business records, becoming the first U.S. president convicted of a felony.
2024: Refusal to Commit
In 2024, Trump refused to commit to accepting the election results.
2024: APSA Ranking
In 2024, members of the American Political Science Association ranked Donald Trump as the worst president.
January 10, 2025: Trump Receives No-Penalty Sentence
On January 10, 2025, the judge gave Trump a no-penalty sentence known as an unconditional discharge.
2025: Executive Orders and Legal Challenges
In 2025, upon taking office, Trump signed a series of executive orders that tested the limits of executive authority and drew immediate legal challenges.
