1987-1988: Trump considers a run for president, while simultaneously juggling large debts stemming from his purchase of the Taj Mahal casino.
2000: Trump enters the presidential race as a Reform Party candidate and receives more than 15,000 votes in the party's California primary.
2003-2004: Trump begins hosting the reality show The Apprentice on NBC, which he also executive-produces. He again mulls a run for president, but ultimately decides not to join the race.
March 2011: A Wall Street Journal/NBC News poll shows Trump leading all presidential contenders, including Mitt Romney.
April 2011: Amid more research polls indicating that he would be the preferred Republican presidential candidate among voters, Trump repeatedly calls for President Obama to release his long-form birth certificate, questioning whether Obama was actually born in the United States. (Obama eventually complies and releases the birth certificate.)
May 2011: Trump officially announces that he will not run for president.
February 2012: Trump endorses Republican candidate Mitt Romney for president.
2013: Trump forms a presidential exploratory committee and, despite a strong backing from Republican voters, announces that he has no interest in running for governor of New York in 2014.
February 2015: Trump decides not to renew his Apprentice contract, fueling speculation that he's mulling a run for president.
June 2015: Trump formally announces that he's running for president in a speech delivered from Trump Tower in New York City. Almost immediately, corporations and individuals that have partnerships with Trump - including Macy's, NBC and Univision - begin to sever ties with the mogul because of disparaging comments he made about Mexicans in the speech announcing his candidacy.
July 2015: Trump comes under fire after revealing Republican rival Lindsey Graham's phone number of live TV and criticizing John McCain for being a prisoner of war in Vietnam.