Paul Ryan’s Attempt to Be Cool on World Emoji Day Backfires

In 1973, the U.S. Justice Department sued Trump's real-estate company, accusing it of refusing to rent apartments in New York and Virginia to African-Americans. Trump countersued the DOJ for defamation, seeking $100 million in damages. Trump settled the case.

Arguably no celebrity has been a bigger target for Trump than Rosie O' Donnell. Their feud began back in 2006, when O'Donnell called Trump a "snake-oil salesman on 'Little House On the Prairie'" on "The View." Trump said he would "look forward to taking lots of money from my nice fat little Rosie."

In the '80s, Trump was a popular target of the satirical publication Spy Magazine. After the magazine called him a "short-fingered vulgarian" in 1988, Trump predicted the magazine's demise and said that his fingers "are long and beautiful, as, it has been well documented, are various other parts of my body.”

Univision dropped Trump's Miss USA pageant from its programming after his comments about Mexican immigrants at the start of his presidential campaign. Trump responded by suing the network for $500 million. The lawsuit was settled in February.

Also Read: Univision’s Jorge Ramos Comes Out Swinging: ‘It’s Not Donald Trump’s Country, This Is Our Country’

Trump ejected Univision's main news anchor, Jorge Ramos, from a news conference during his campaign. Ramos had attempted to ask Trump about his immigration policies. "Go back to Univision," Trump said.

Also Read: Jorge Ramos Doubles Down Against Donald Trump: He’s ‘Fomenting Hatred’

Former Miss USA contestant Sheena Monnin accused the pageant, which Trump owns, of being rigged. Trump responded by filing and winning a $5 million defamation lawsuit against Monnin. She later said her situation with Trump "has been resolved" and that no money was paid out of my pocket." 

Also Read: Miss USA Speaks Out on Donald Trump Mexican Flap to CNN’s Don Lemon: He Has ‘Right to Free Speech’

Trump repeatedly attacked Sen. Ted Cruz during the Republican Primary. The most infamous attack came on March 22, when he threatened to "spill the beans" on Cruz's wife on Twitter after a Super PAC affiliated with Cruz posted a picture of Trump's wife, Melania, from a nude GQ photo shoot. Cruz endorsed Trump last week.

Also Read: Donald Trump Threatens Ted Cruz’s Wife: ‘Be Careful or I Will Spill the Beans’

In 1993, Trump's Atlantic City casino was falling behind the Foxwoods Resort Casino in Connecticut, which is owned by the Mashantucket Pequot Tribal Nation. Trump's reaction? While testifying before a Congressional subcommittee, he claimed that "it’s obvious that organized crime is rampant on the Indian reservations" and that the Pequot "don't look like Indians to me."

In 2011, Trump repeatedly demanded President Barack Obama's birth certificate, claiming he wasn't born in the United States. After Obama released the birth certificate, he belittled Trump during the White House Correspondents Dinner.

In an interview with "Today," Cole Bolton, editor-in-chief of The Onion, revealed the humor site received a letter from Trump's lawyer over a satirical op-ed supposedly from Trump entitled, "When You're Feeling Low, Just Remember I'll Be Dead In 15 or 20 Years."

Trump also attempted to sue Bill Maher when the comedian joked on "Real Time" that if Trump could provide proof that his biological father is not an orangutan, he would donate $5 million to the charity of Trump's choice. Trump took him up on that offer, and then sued to try to get Maher to pay the money. The lawsuit was later withdrawn.

The success of "The Apprentice" inspired NBC to make a spinoff starring Martha Stewart. But Trump wrote an open letter blasting Stewart for the show failing to take off. "I knew it would fail as soon as I first saw it -- and your low ratings bore me out," he wrote.

Also Read: Martha Stewart Living Omnimedia to Be Sold for $353 Million

In a May 15 front page New York Times article, former Miss Universe Alicia Machado accused Trump of using her weight problems as a media opportunity shortly after she won the Miss Universe pageant. "He's always been white trash, a racist, a horrible person," she said.

Sen. Elizabeth Warren tweeted that Trump sounded like a "two-bit dictator" and a "pathetic coward who can't stand that he's losing to a girl." Trump has responded by calling Warren "Pocahontas," referring to Warren's contested claim in 2012 that she had Native American ancestry.

Perhaps Trump's most famous confrontation this year was with Khizr and Ghazala Khan, whose son was killed in the Iraq War. Khzir Khan declared that Trump "sacrificed nothing and no one," to which Trump suggested that Khan's wife did not speak at the convention because she "wasn't allowed to."