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 a member of the Republican Party. Currently, he holds the position of 47th president of the United States. His career spans real estate, television, and politics, marked by significant policy changes and a distinctive communication style. He remains a prominent and often controversial figure in American public life.
1973: Trump countersues the U.S. government
In 1973, Donald Trump countersued the U.S. government for $100 million (equivalent to $708 million in 2024) over charges of racially discriminatory practices.
1976: Trump refused to release tax returns
Since 1976, every major candidate released tax returns.
1985: League Folded
In 1985, after the 1985 season, the United States Football League folded, largely due to Donald Trump's attempt to move to a fall schedule.
1991: Default on Loans for Trump Shuttle
In 1991, Donald Trump defaulted on his loans for Trump Shuttle, and ownership passed to the banks.
1991: Trump Taj Mahal Bankruptcy Filing
In 1991, Donald Trump filed for Chapter 11 bankruptcy protection for the Trump Taj Mahal.
1991: Trump's hotel and casino businesses filed for bankruptcy protection
In 1991, Donald Trump's over-leveraged hotel and casino businesses in Atlantic City and New York filed for Chapter 11 bankruptcy protection.
1992: Bankruptcy Filing for Trump Castle and Trump Plaza
In 1992, both Trump Castle and Trump Plaza casinos filed for Chapter 11 bankruptcy protection.
1992: Plaza Hotel 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: Sale of Interest in Riverside South Project
In 1994, struggling with debt from other ventures, Donald Trump sold most of his interest in the Riverside South project to Asian investors.
1995: Trump declared loss of $916 million
In 1995, Donald Trump declared a loss of $916 million which could have let him avoid taxes for up to 18 years.
1995: Default on Bank Loans and Seizure of Properties
In 1995, Donald Trump defaulted on over $3 billion of bank loans, and the lenders seized the Plaza Hotel and most of his other properties.
2004: Trump Hotels & Casino Resorts (THCR) Bankruptcy
In 2004, Trump Hotels & Casino Resorts (THCR) went bankrupt, leaving Donald Trump with 10 percent ownership.
2009: Trump Hotels & Casino Resorts Bankruptcy
In 2009, Donald Trump filed for Chapter 11 bankruptcy protection for the Trump Hotels & Casino Resorts company.
2009: Trump's hotel and casino businesses filed for bankruptcy protection
In 2009, Donald Trump's over-leveraged hotel and casino businesses in Atlantic City and New York filed for Chapter 11 bankruptcy protection.
2010: Trump University renamed
In 2010, after being notified by New York State authorities that the use of "university" violated state law because it was not an academic institution, Trump University was renamed the Trump Entrepreneur Initiative.
2013: New York State filed 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.
2014: Trump promised to release tax returns
In 2014, Donald Trump promised to release his tax returns if he ran for office.
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.
2015: Trump promised to release tax returns
In 2015, Donald Trump promised to release his tax returns if he ran for office.
July 2016: FBI Launches Crossfire Hurricane
In July 2016, the FBI initiated Crossfire Hurricane, an investigation into potential connections between Russia and Donald Trump's 2016 campaign.
October 2016: Trump's state filings leaked
In October 2016, portions of Donald Trump's state filings for 1995 were leaked to a reporter from The New York Times, revealing he had declared a loss of $916 million.
December 2016: Trump's team announced dissolution of the Donald J. Trump Foundation
In December 2016, Donald Trump's team announced that the Donald J. Trump Foundation would be dissolved.
2016: Cover Up of Alleged Affair
Donald Trump booked Michael Cohen's hush-money payments to adult film actress Stormy Daniels as business expenses to cover up his alleged affair with Daniels during the 2016 election.
2016: Trump supported the use of interrogation torture methods.
In 2016, Trump said he supported the use of interrogation torture methods "a hell of a lot worse than waterboarding."
January 2017: Trump signs executive order denying entry to citizens of seven Muslim-majority countries.
In January 2017, Trump signed an executive order that temporarily denied entry to citizens of seven Muslim-majority countries, causing protests and legal challenges.
January 2017: Intelligence Agencies Report on Russian Interference
In January 2017, U.S. intelligence agencies jointly stated with "high confidence" that Russia interfered in the 2016 presidential election to favor Donald Trump.
May 2017: Trump dismissed FBI director James Comey.
In May 2017, Trump dismissed FBI director James Comey, saying he was concerned about Comey's role in the Trump-Russia investigations.
May 2017: FBI Opens Second Investigation After Comey Firing
In May 2017, following the firing of James Comey, the FBI launched a second investigation into Donald Trump's personal and business dealings with Russia.
October 2017: Hundreds of sub-cabinet positions remain without a nominee.
In October 2017, hundreds of sub-cabinet positions remained without a nominee in the Trump administration.
December 2017: Supreme Court allows travel ban to go into effect.
In December 2017, the Supreme Court allowed Trump's revised travel ban to go into effect.
2017: Trump comments on Unite the Right rally.
Trump's comments on the 2017 Unite the Right rally, condemning "this egregious display of hatred, bigotry and violence on many sides" and stating that there were "very fine people on both sides", were criticized as implying a moral equivalence between the white supremacist demonstrators and the counter-protesters.
January 2018: Trump refers to El Salvador, Haiti, Honduras, and African nations as "shithole countries."
In January 2018, during a discussion of immigration legislation, Trump reportedly referred to El Salvador, Haiti, Honduras, and African nations as "shithole countries." His remarks were widely condemned as racist.
June 2018: Trump mandates migrant families be detained together.
In June 2018, Trump acceded to public pressure and mandated that migrant families be detained together unless there is a concern of risk for the child, in response to public outrage over family separations at the border.
June 2018: New York attorney general's office filed civil suit 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.
June 2018: Trump administration argues to eliminate Obamacare
In June 2018, the Trump administration joined 18 Republican-led states in arguing before the Supreme Court that eliminating the financial penalties associated with the individual mandate had rendered the Affordable Care Act unconstitutional. Their pleading would have eliminated health insurance coverage for up to 23 million Americans, but was unsuccessful.
July 2018: High staff turnover in the Trump administration.
By early 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 begins due to border wall funding dispute.
In December 2018, Trump's refusal to sign any spending bill unless it allocated funding for the border wall resulted in the longest-ever federal government shutdown, lasting 35 days.
December 2018: Trump Foundation ceased operation
In December 2018, the Donald J. Trump Foundation ceased operation and disbursed its assets to other charities.
2018: Trump signed legislation to increase funding for drug treatments.
In 2018, Trump signed legislation to increase funding for drug treatments in response to the opioid epidemic but was criticized for lacking a concrete strategy.
2018: USA Today review of Trump's legal actions
In 2018, USA Today conducted a review of state and federal court files, revealing that Donald Trump and his businesses had been involved in more than 4,000 state and federal legal actions.
2018: 2018 revenues were 7.6 percent lower than projected
In 2018, revenues were 7.6 percent lower than projected.
January 8, 2019: Many key positions in the executive branch remained unfilled.
By January 8, 2019, of 706 key positions in the executive branch, 433 had been filled, and there was no nominee for 264.
January 2019: Government shutdown ends without border wall funding.
In January 2019, the government shutdown ended after Trump agreed to fund the government without any funds for the wall.
March 2019: Mueller Submits Final Report
In March 2019, Robert Mueller submitted his final report, which found that Russia interfered in the 2016 election to favor Donald Trump, who welcomed the effort, but that evidence did not establish a conspiracy.
April 2019: House Oversight Committee Issues Subpoenas
In April 2019, the House Oversight Committee issued subpoenas seeking financial details from Donald Trump's banks, Deutsche Bank and Capital One, and his accounting firm, Mazars USA, leading to legal challenges.
July 2019: Trump's racist comments against Democratic congresswomen.
In July 2019, Trump tweeted that four Democratic congresswomen, all minorities, should "go back" to the countries they "came from." The House of Representatives condemned his "racist comments".
October 2019: Talks between US and North Korea break down.
In October 2019, talks between the U.S. and North Korea broke down and no denuclearization agreement was reached.
November 2019: Trump ordered to pay charities for misusing foundation 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 of Representatives voted to impeach Donald Trump for abuse of power and obstruction of Congress, stemming from his interactions with the Ukrainian president.
2019: Trump Impeachment
In 2019, Donald Trump was impeached for abuse of power and obstruction of Congress; the Senate acquitted him.
2019: E. Jean Carroll Accuses Trump of Rape
In 2019, journalist E. Jean Carroll accused Donald 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 Trump's travel ban.
2019: Federal budget deficit increased
In 2019, the federal budget deficit increased by almost 50 percent, to nearly $1 trillion.
January 2020: Trump considers cuts to Medicare and social safety-net programs
In January 2020, Trump expressed a willingness to consider cuts to Medicare and other social safety-net programs, going back on his 2016 campaign promises.
February 2020: Trump Acquitted by the Senate
In February 2020, Donald Trump was acquitted by the Senate following his impeachment by the House of Representatives.
February 2020: COVID-19 recession began
In February 2020, the COVID-19 recession began, ending the longest economic expansion in American history that started in 2009.
April 2020: Trump halted funding of the World Health Organization.
In April 2020, after weeks of attacks to draw attention away from his slow response to the Coronavirus, Trump halted funding of the World Health Organization.
June 2020: Controversial removal of protesters and photo-op at St. John's Episcopal Church.
In June 2020, during the George Floyd protests, federal law-enforcement officials controversially removed protesters from Lafayette Square. Trump then posed with a Bible for a photo-op at St. John's Episcopal Church, drawing condemnation.
August 2020: Federal Judge Halts Trump Administration's rollback of anti-discrimination protections for transgender patients.
In August 2020, a federal judge halted the Trump administration's attempted rollback of anti-discrimination protections for transgender patients after a Supreme Court ruling extended employees' civil rights protections to gender identity and sexual orientation.
November 2020: Biden Wins 2020 Election
In November 2020, Joe Biden won the presidential election, receiving 81.3 million votes to Donald Trump's 74.2 million. Trump declared victory prematurely and alleged election fraud.
December 2020: Reports Emerge of Military on "Red Alert"
In December 2020, reports emerged that the U.S. military was on "red alert" due to concerns that Donald Trump might declare martial law or initiate military action.
2020: Trump's False Claims and Republican Party Voting Restrictions
Following his 2020 election defeat, Donald Trump's continuing false claims concerning the 2020 election were used by the Republican Party to justify imposing new voting restrictions in its favor.
2020: COVID-19 Pandemic Response
In 2020, during the COVID-19 pandemic, President Trump downplayed its severity, contradicted health officials, and signed the CARES Act.
2020: Trump's Efforts to Overturn the 2020 Election
In connection with Donald Trump's efforts to overturn the 2020 election, the U.S. House committee recommended criminal charges against him.
January 6, 2021: Trump Addresses Rally and Supporters Attack Capitol
On January 6, 2021, Donald Trump held a rally at the Ellipse, urging supporters to march to the Capitol. Following the rally, his supporters attacked the Capitol building while Congress was certifying the election results.
January 13, 2021: House Charges Trump with Incitement of Insurrection
On January 13, 2021, the House of Representatives charged Donald Trump with incitement of insurrection following the January 6 attack on the U.S. Capitol.
February 2021: Supreme Court allowed release of Trump's tax returns
In February 2021, the U.S. Supreme Court allowed the release of Donald Trump's tax returns and other records to the Manhattan district attorney for a criminal investigation.
2021: Refugee admissions reduced to record lows.
By 2021, Trump reduced the number of refugees admitted to record lows, from an annual limit of 110,000 before he took office to 15,000.
2021: January 6 Capitol Attack
In 2021, after losing the 2020 presidential election, Donald Trump attempted to overturn the result, culminating in the January 6 Capitol attack. Also in 2021, he was impeached for incitement of insurrection.
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, that Donald Trump had taken to Mar-a-Lago after leaving the White House.
July 2022: Trump Continues to Pressure State Legislators
As of July 2022, Donald Trump continued to pressure state legislators to overturn the 2020 election results.
August 8, 2022: FBI Searches Mar-a-Lago
On August 8, 2022, FBI agents searched Mar-a-Lago for illegally held documents, including those in breach of the Espionage Act, collecting 11 sets of classified documents.
September 2022: Settlement Reached with Mazars USA
In September 2022, Donald 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 Donald Trump for obstructing an official proceeding, conspiracy to defraud the United States, and inciting or assisting an insurrection.
2022: Civil Lawsuits and Judgements
In 2022, E. Jean Carroll sued Donald Trump again for battery and more defamation. New York also filed a civil lawsuit against Trump accusing him of inflating the Trump Organization's value. He was later found liable in both cases.
June 2023: Trump Indicted on Espionage Act Charges
In June 2023, a federal grand jury indicted Donald Trump on 31 counts of "willfully retaining national defense information" under the Espionage Act, among other charges, and he pleaded not guilty.
August 2023: Trump Indicted in Georgia
In August 2023, Donald Trump was indicted on 13 charges, including racketeering, by a grand jury in Fulton County, Georgia for his efforts to subvert the 2020 election in the state.
December 2023: Colorado Supreme Court Rules Trump Disqualified
In December 2023, the Colorado Supreme Court ruled Donald Trump disqualified for the Colorado Republican primary due to his role in inciting the January 6, 2021, attack on Congress.
2023: Legal Liabilities
In 2023, Donald Trump was found liable in civil cases for sexual abuse and defamation and for business fraud.
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.
July 13, 2024: Trump Survives Assassination Attempt
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 classified documents case, ruling Special Counsel Jack Smith's appointment as special prosecutor was unconstitutional.
2024: Trump Refuses to Commit to Accepting Election Results
In 2024, Donald Trump refused to commit to accepting the election results.
2024: Conviction and Election
In 2024, Donald Trump was found guilty of falsifying business records, becoming the first U.S. president convicted of a felony. He won the 2024 presidential election against Kamala Harris.
January 10, 2025: Trump Given No-Penalty Sentence
On January 10, 2025, the judge gave Donald Trump a no-penalty sentence known as an unconditional discharge.
2025: Executive Orders and Clemency
In 2025, after taking office, Donald Trump signed a series of executive orders, some mirroring Project 2025 proposals, and granted clemency to January 6 rioters. These actions faced legal challenges and were criticized for potentially violating federal laws and contributing to democratic backsliding.
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