Rise to Success: Career Highlights of Donald Trump
From career breakthroughs to professional milestones, explore how Donald Trump made an impact.
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.
1968: Employment at Trump Management
In 1968, Donald Trump began working at Trump Management, his father's real estate company, managing apartment complexes.
1970: Investment in Broadway Comedy
In 1970, Donald Trump invested $70,000 in a Broadway comedy, losing the money.
1971: Trump Takes Over Family Business
In 1971, Donald Trump became the president of his family's real estate business, renaming it the Trump Organization.
1971: Move to Manhattan and Presidency of Trump Organization
In 1971, Donald Trump moved to Manhattan and became the president of the Trump Organization, with his father becoming chairman.
1979: Introduction to Roger Stone
In 1979, Roy Cohn introduced Donald Trump to political consultant Roger Stone, who was enlisted to deal with the federal government.
1980: Grand Hyatt Hotel Opens and Trump Tower Development
In 1980, the Grand Hyatt Hotel reopened, and Donald Trump obtained rights to develop Trump Tower.
1983: Purchase of New Jersey Generals
In 1983, Donald Trump purchased the New Jersey Generals, a team in the United States Football League.
1984: Opening of Harrah's at Trump Plaza
In 1984, Donald Trump opened Harrah's at Trump Plaza, a hotel and casino, with the Holiday Corporation.
1985: Cameos in film and television
From 1985 to 2001, Donald Trump had cameos in many films and television shows.
1985: Acquisition of Mar-a-Lago Estate
In 1985, Donald Trump acquired the Mar-a-Lago estate in Palm Beach, Florida.
1985: Purchase of Trump's Castle
In 1985, Donald Trump bought the unopened Atlantic City Hilton Hotel and renamed it Trump's Castle.
May 1986: Sole Control of Harrah's at Trump Plaza
In May 1986, Donald Trump paid Holiday Corporation $70 million to take sole control of Harrah's at Trump Plaza.
1986: Purchased shares in public companies
In 1986, Donald Trump began purchasing significant blocks of shares in various public companies while suggesting intentions of taking over the companies, leading to speculation about greenmail.
1987: Advertisements on foreign policy views
In 1987, Donald Trump placed full-page advertisements in major newspapers, expressing his views on foreign policy and how to eliminate the federal budget deficit.
1987: Publication of "The Art of the Deal"
In 1987, Donald Trump's first book, "The Art of the Deal", was published and became a New York Times Best Seller.
1988: Acquisition of the Plaza Hotel
In 1988, Donald Trump acquired the Plaza Hotel with a loan from a consortium of 16 banks.
1988: Asked to be George H.W. Bush's running mate
In 1988, Donald Trump approached Lee Atwater, asking to be put into consideration to be Republican nominee George H. W. Bush's running mate, but Bush found the request "strange and unbelievable".
1988: Purchase of Trump Taj Mahal
In 1988, Donald Trump bought the Trump Taj Mahal in Atlantic City.
1988: Sold shares for profit
In 1988, Donald Trump sold his shares for a profit after suggesting he intended to take over companies, but The New York Times reported that investors stopped taking his takeover talk seriously afterwards.
1988: Trump purchased Eastern Air Lines Shuttle
In 1988, Trump purchased the Eastern Air Lines Shuttle for $380 million (equivalent to $1.03 billion in 2025), financed by loans, and renamed it Trump Shuttle.
1988: Establishment of the Donald J. Trump Foundation
In 1988, the Donald J. Trump Foundation, a private foundation, was established.
1989: Joined SAG-AFTRA
In 1989, Donald Trump joined SAG-AFTRA as a member. He would later resign in 2021.
1989: Tour de Trump Cycling Stage Race
In 1989, Donald Trump lent his name to the Tour de Trump cycling stage race.
April 1990: Opening of Trump Taj Mahal
In April 1990, the Trump Taj Mahal opened, financed with $675 million in junk bonds and completed for $1.1 billion.
1990: Tour de Trump Cycling Stage Race
In 1990, Donald Trump lent his name to the Tour de Trump cycling stage race.
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: 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: Trump Shuttle operated until 1992
Trump Shuttle operated until 1992, after Trump purchased it in 1988 and later defaulted on his loans in 1991.
1995: Conversion of Mar-a-Lago into a Private Club
In 1995, Donald Trump converted the Mar-a-Lago estate into a private club.
1995: Founding of Trump Hotels & Casino Resorts
In 1995, Donald Trump founded Trump Hotels & Casino Resorts (THCR), which assumed ownership of the Trump Plaza.
1996: Purchase of Miss Universe pageants
In 1996, Donald Trump purchased the Miss Universe pageants, which included Miss USA and Miss Teen USA.
1996: THCR Purchases Taj Mahal and Trump Castle
In 1996, Trump Hotels & Casino Resorts (THCR) purchased the Taj Mahal and the Trump Castle.
1999: Building and Buying Golf Courses
In 1999, Donald Trump began building and buying golf courses.
February 2000: Withdrawal from Reform Party primaries
In February 2000, Donald Trump withdrew from the 2000 Reform Party presidential primaries after being a candidate for three months.
2001: End of cameos in film and television
From 1985 to 2001, Donald Trump had cameos in many films and television shows.
2002: Move of pageants to NBC
In 2002, due to disagreements with CBS, Donald Trump moved the Miss Universe and Miss USA pageants to NBC.
2004: Start of 'Trumped!' radio program
From 2004 to 2008, Donald Trump had his own short-form talk radio program called Trumped!.
2004: Hosting The Apprentice
In 2004, Donald Trump began hosting The Apprentice, a reality show created by Mark Burnett, where he eliminated contestants with the phrase "you're fired".
2005: Cofounded Trump University
In 2005, Donald Trump cofounded Trump University, a company selling real estate seminars costing up to $35,000.
2006: Trump's donations spent
By the end of 2006, the $5.4 million that Donald Trump gave to his foundation from 1987 to 2006 had been spent.
2007: Donations in 2007-2008
After donating a total of $65,000 in 2007-2008, Donald Trump stopped donating any personal funds to the Donald J. Trump Foundation.
2007: Appearance at WrestleMania 23
In 2007, Donald Trump played himself as a super-rich boss at WrestleMania 23, an event staged by professional wrestling promotion WWE.
2008: End of 'Trumped!' radio program
From 2004 to 2008, Donald Trump had his own short-form talk radio program called Trumped!.
2009: Trump's Departure as Chairman of THCR
In 2009, Donald Trump remained chairman of Trump Hotels & Casino Resorts until 2009.
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.
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.
May 2011: Announcement not to run in 2012
In May 2011, Donald Trump announced that he would not challenge President Barack Obama in the 2012 election.
2011: Guest commentator on Fox & Friends
From 2011 until 2015, Donald Trump was a guest commentator on Fox & Friends.
2012: Considered challenging President Barack Obama
In 2011, Donald Trump considered challenging President Barack Obama in the 2012 election. He spoke at the Conservative Political Action Conference in February and gave speeches in states with early primaries.
June 2015: Announcement of 2016 candidacy
In June 2015, Donald Trump announced his candidacy for the 2016 presidential election.
2015: End of hosting The Apprentice
From 2004 to 2015, Donald Trump hosted The Apprentice, a reality show created by Mark Burnett. He hosted a variant called the Celebrity Apprentice as well.
2015: End as guest commentator on Fox & Friends
From 2011 until 2015, Donald Trump was a guest commentator on Fox & Friends.
2015: Final Season of The Apprentice
In 2015, Donald Trump hosted the final season of the reality television show "The Apprentice".
March 2016: Republican front-runner
In March 2016, Donald Trump became the Republican front-runner in the presidential race.
2016: Golf Course Holdings
By 2016, Donald Trump owned 17 golf courses globally.
2016: Emergence of Trumpism
During his 2016 campaign, Trump's politics and rhetoric resulted in the formation of Trumpism, a political movement that has been compared to a cult of personality.
2016: Campaign promises and positions
During his 2016 presidential campaign, Donald Trump advocated for renegotiating trade agreements, enforcing immigration laws, building a wall on the Mexico-U.S. border, increasing military spending, and more.
2016: Pledge to Overturn Roe v. Wade
During the 2016 campaign, Donald Trump pledged that Roe v. Wade would be overturned "automatically" if he were elected and given the opportunity to appoint two or three anti-abortion justices.
2016: Trump Wins Presidential Election
In 2016, Donald Trump won the presidential election against Hillary Clinton.
2016: Free Media Coverage and Press Accusations
In the 2016 campaign, Trump benefited from a record amount of free media coverage, estimated at $2 billion. He also frequently accused the press of bias, calling it the "fake news media" and "the enemy of the people".
January 20, 2017: Inauguration as President
On January 20, 2017, Donald Trump was inaugurated as President of the United States. The day after, there were Women's Marches worldwide.
December 2017: Signed Tax Cuts and Jobs Act
In December 2017, Donald Trump signed the Tax Cuts and Jobs Act of 2017, which reduced tax rates for businesses and individuals.
2017: Donald Trump Becomes 45th President
In 2017, Donald Trump began his term as the 45th president of the United States.
2017: Trump Files for Reelection
In 2017, Donald Trump filed to run for reelection only a few hours after becoming president.
June 2018: First Meeting with Kim Jong Un
In June 2018, Donald Trump became the first sitting U.S. president to meet a North Korean leader, Kim Jong Un.
2018: Licensing Deals
By 2018, only two consumer goods companies continued to license Donald Trump's name.
2018: Signed opioid legislation
In 2018, Donald Trump signed legislation to increase funding for drug treatments in response to the opioid epidemic.
June 2019: Second Meeting with Kim Jong Un
In June 2019, Donald Trump met Kim Jong Un for the third time.
August 2020: Trump Officially Becomes Republican Nominee
In August 2020, Donald Trump officially became the Republican nominee for the presidential election.
2020: Wins 2024 Presidential Election
In 2020, Donald Trump won the 2024 presidential election against Vice President Kamala Harris, was given a no-penalty sentence, and two federal felony indictments against him for retention of classified documents and obstruction of the 2020 election were dismissed without prejudice.
2021: End of Presidential Term
In 2021, Donald Trump's term as the 45th president of the United States concluded.
2021: Resignation from SAG-AFTRA
In 2021, Donald Trump, a member since 1989, resigned from SAG-AFTRA to avoid a disciplinary hearing regarding the January 6 attack.
February 2022: Launch of Truth Social
In February 2022, Donald Trump's Trump Media & Technology Group (TMTG) launched Truth Social, a pro-Trump social media platform.
March 2024: Trump Media & Technology Group Becomes a Public Company
In March 2024, Donald Trump's Trump Media & Technology Group (TMTG) became a public company.
November 2024: Trump wins the 2024 presidential election
In November 2024, Donald Trump won the election with 312 electoral votes to incumbent vice president Kamala Harris's 226. He also won the popular vote with 49.8% to Harris's 48.3%.
2024: Increased Fearmongering During Campaign
During his 2024 presidential campaign, Trump's rhetoric intensified with fearmongering and demagogy. He regularly vilified his political opponents.
January 20, 2025: Trump begins his second term
On January 20, 2025, Donald Trump began his second term as president, becoming the oldest to assume the presidency, the first president with a felony conviction, and the second person to serve two nonconsecutive terms.
February 2025: Musk as Special Government Employee
In February 2025, the White House declared Elon Musk a special government employee, granting his Department of Government Efficiency (DOGE) access to numerous federal agencies. Musk's teams operated within eighteen departments, including the Treasury Department, the Small Business Administration, and the General Services Administration.
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