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, he is also the 47th President of the United States.

Sections (6)

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

1973: Countersues the U.S. Government

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

1985: USFL Folded After Attempt to Move to Fall Schedule

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

1991: First bankruptcy protection

In 1991, Donald Trump began filing for Chapter 11 bankruptcy protection for six of his businesses.

1991: Defaults on Trump Shuttle Loans

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

1991: Trump Taj Mahal Bankruptcy

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

1991: First Bankruptcy Filing for Trump's Businesses

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: Formation of All County Building Supply & Maintenance Corp.

In 1992, Donald Trump, along with his siblings and cousin, formed All County Building Supply & Maintenance Corp., which is alleged to have been a shell company for marking up vendor costs.

1992: Casinos File for Bankruptcy Protection

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 the banks took control of the property.

1994: Sells 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: Defaults on Bank Loans

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

2004: THCR Bankruptcy

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

2009: Filing for bankruptcy protection

In 2009, Donald Trump ended the period where he filed for Chapter 11 bankruptcy protection for six of his businesses.

2009: Sixth Bankruptcy Filing for Trump's Businesses

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.

2010: Trump University Renamed

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

2013: New York State Files 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. Two class actions were also filed in federal court.

June 2015: NBC and Univision Drop Pageants

In June 2015, NBC and Univision dropped the Miss Universe and Miss USA pageants in reaction to Donald Trump's comments about Mexican immigrants.

Loading Video...

July 2016: FBI launched Crossfire Hurricane

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

December 2016: Announcement of the Donald J. Trump Foundation dissolution

In December 2016, Donald Trump's team announced that The Donald J. Trump Foundation would be dissolved.

2016: Settlement of Trump University Lawsuits

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.

2016: Cover up with Stormy Daniels during the 2016 election

The case stemmed from evidence that he booked Michael Cohen's hush-money payments to adult film actress Stormy Daniels as business expenses to cover up his alleged 2006–2007 affair with Daniels during the 2016 election.

2016: Trump used "rigged election" and "election interference"

Trump mentioned "rigged election" and "election interference" earlier and more frequently than in the 2016 and 2020 campaigns.

January 2017: Trump signs executive order temporarily 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, resulting in protests and legal challenges.

January 2017: Intelligence agencies reported 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 opened second investigation after Comey firing

In May 2017, after 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 without a nominee

In October 2017, there were hundreds of sub-cabinet positions 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 the revised version of Trump's travel ban to go into effect.

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, after initially blaming Democrats and insisting he could not stop the family separation policy with an executive order.

June 2018: New York Attorney General's Office Files 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 the elimination of 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 turnover rate among senior aides

As of 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: The Donald J. Trump Foundation Ceases Operation

In December 2018, The Donald J. Trump Foundation ceased operation and disbursed its assets to other charities.

December 2018: Federal government shutdown begins

In December 2018, Trump's refusal to sign any congressional spending bill unless it allocated funding for the border wall resulted in the longest-ever federal government shutdown, for 35 days.

2018: Review of Trump's Legal Actions by USA Today

According to a review 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: Lower-than-Projected Government Revenue

In 2018, government revenues were 7.6 percent lower than projected, following the signing of the Tax Cuts and Jobs Act of 2017.

2018: Trump signed legislation in response to opioid epidemic

In 2018, in response to the opioid epidemic, Trump signed legislation to increase funding for drug treatments, but was widely criticized for failing to make a concrete strategy.

2018: Disclosure of inheritance by the New York Times

In 2018, the New York Times reported that Donald Trump borrowed at least $60 million from his father, largely did not repay the loans, and received another $413 million (2018 equivalent, adjusted for inflation) from his father's company.

January 8, 2019: Many key positions unfilled in Trump administration

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

January 2019: Federal government shutdown ends

In January 2019, the federal government shutdown ended after Trump agreed to fund the government without any funds for the border wall.

March 2019: Mueller submitted final report

In March 2019, Robert Mueller submitted his final report, finding that Russia interfered in the 2016 election to favor Trump, and that Trump's campaign welcomed the effort, but the evidence did not establish a conspiracy.

April 2019: House Oversight Committee issued subpoenas

In April 2019, the House Oversight Committee issued subpoenas seeking financial details from Trump's banks, Deutsche Bank and Capital One, and his accounting firm, Mazars USA.

October 2019: Talks with 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 $2 Million 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 voted to impeach Trump

In December 2019, the House of Representatives 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; he was later acquitted by the Senate.

2019: E. Jean Carroll accused 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.

2019: Supreme Court upholds travel ban

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

2019: Federal Budget Deficit Increase

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

January 2020: Trump expresses willingness to consider cuts to Medicare and other social safety-net programs

In January 2020, despite promising to protect funding for Medicare and other social safety-net programs during the 2016 campaign, Trump expressed willingness to consider cuts to them.

February 2020: Start of COVID-19 Recession

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

February 2020: Senate acquitted Trump

In February 2020, the Senate acquitted Trump on the impeachment charges brought by the House of Representatives.

April 2020: Trump halts funding of the World Health Organization

In April 2020, after weeks of attacks to draw attention away from his slow response to COVID-19, Trump halted funding of the World Health Organization.

June 2020: Controversial removal of protesters from Lafayette Square

In June 2020, during the George Floyd protests, federal law-enforcement officials controversially removed a largely peaceful crowd of lawful protesters from Lafayette Square, outside the White House. Trump then posed with a Bible for a photo-op at the nearby St. John's Episcopal Church, with religious leaders condemning both the treatment of protesters and the photo opportunity itself.

August 2020: Attempted rollback of anti-discrimination protections halted

In August 2020, 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: Biden won the 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. Trump alleged election fraud.

December 2020: Reports of U.S. military on "red alert"

In December 2020, reports surfaced that the U.S. military was on "red alert," and ranking officers had discussed potential actions if Trump declared martial law. Concerns arose among officials like Mark Milley and Gina Haspel regarding possible coup attempts or military actions.

2020: Cases dismissed after reelection

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: Loses Presidential Election

In 2020, Donald Trump lost the presidential election to Joe Biden and then attempted to overturn the results.

2020: Trump's efforts to overturn the 2020 election

In connection with Trump's efforts to overturn the 2020 election and his involvement in the January 6 attack, in December 2022 the U.S. House committee on the attack recommended criminal charges against him.

2020: Trump used "rigged election" and "election interference"

Trump mentioned "rigged election" and "election interference" earlier and more frequently than in the 2016 and 2020 campaigns.

January 6, 2021: Trump held a rally and his supporters attacked the Capitol

On January 6, 2021, Trump held a rally in Washington, D.C., urging his supporters to march to the Capitol. His supporters then attacked the Capitol building while Congress was certifying the presidential election results. He posted on social media but did not ask the rioters to disperse until 6 p.m., when he told them to "go home with love & in peace".

January 13, 2021: House charged Trump with incitement of insurrection

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

February 2021: Supreme Court Allows Release of Trump's Tax Returns

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

2021: Second Impeachment

In 2021, Donald Trump was impeached for incitement of insurrection, but the Senate acquitted him.

2021: Refugee admissions reduced to record lows

In 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 attempting to overturn the 2020 election results, the January 6 Capitol attack occurred.

January 2022: National Archives retrieved documents from Mar-a-Lago

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

July 2022: Trump continued to pressure state legislators to overturn the election

As of July 2022, Trump continued to pressure state legislators to overturn the 2020 election results.

August 8, 2022: FBI searched 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, some marked top secret.

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 recommended criminal charges against Trump

In December 2022, the U.S. House committee recommended criminal charges against Trump for obstructing an official proceeding, conspiracy to defraud the United States, and inciting or assisting an insurrection.

2022: Carroll sued Trump again

In 2022, E. Jean Carroll sued Trump again for battery and more defamation, and New York filed a civil lawsuit against Trump accusing him of inflating the Trump Organization's value.

March 2023: Campaign began diverting donations

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, Special Counsel Jack Smith indicted Trump on 31 counts of "willfully retaining national defense information" under the Espionage Act, among other charges.

August 2023: Trump indicted in Georgia

In August 2023, 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 ruled Trump disqualified

In December 2023, the Colorado Supreme Court ruled Trump disqualified for the Colorado Republican primary for his role in inciting the January 6, 2021, attack on Congress.

2023: Civil Case Liabilities

In 2023, Donald Trump was found 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 to Stormy Daniels during the 2016 election.

July 13, 2024: Trump shot in assassination attempt

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

July 2024: Judge dismissed case

In July 2024, judge Aileen Cannon dismissed the case, ruling Smith's appointment as special prosecutor was unconstitutional.

2024: Conviction for Falsifying Business Records

In 2024, Donald Trump was found guilty of falsifying business records, becoming the first U.S. president convicted of a felony. Subsequently, after winning the 2024 presidential election against Kamala Harris, he was sentenced to a penalty-free discharge, and two other felony indictments against him were dismissed.

2024: IRS Investigation Reported

In 2024, The New York Times and ProPublica reported that the Internal Revenue Service was investigating Donald Trump for potentially writing off losses improperly.

2024: Trump refused to commit to accepting the 2024 election results

Trump mentioned "rigged election" and "election interference" earlier and more frequently than in the 2016 and 2020 campaigns and refused to commit to accepting the 2024 election results.

January 10, 2025: Judge gave Trump a no-penalty sentence

On January 10, 2025, the judge gave Trump a no-penalty sentence known as an unconditional discharge.

March 2025: Attempt to use Alien Enemies Act to deport migrants

In March 2025, Trump attempted to use the Alien Enemies Act of 1798 for the first time since World War II to deport migrants, but was temporarily blocked by a federal judge.