The Most Head-Turning Comments Made About Donald Trump

U.S. presidents draw more criticism than an overworked political cartoonist. When President Barack Obama had "the audacity of taupe" to wear a tan suit during a 2014 press conference, pundits and Republicans pounced. Congressman Pete King proclaimed, "I don't think any of us can excuse what the president did" because Obama allegedly projected "a lack of seriousness" while "ISIS [was] watching."  That same year, future president Donald Trump tweeted, "The United States, under President Obama, has truly become the 'gang that couldn't shoot straight.' Everything he touches turns to garbage!" 

After clinching the presidency in 2016, Donald Trump — who famously declared during his candidacy, "I could stand in the middle of Fifth Avenue and shoot somebody, okay, and I wouldn't lose any voters" –  would have his political Teflon tested by sexual assault allegations, financial scandals, accusations of racism, election meddling by Russia, and other controversies. Along the way, devoted supporters and detractors have weighed in. Here are some of the most head-turning statements about Donald Trump.

Adult film star Stormy Daniels first went on the record about her alleged affair with Donald Trump in a 2011 interview with In Touch Weekly. She described Trump as a "pretty fascinating" guy who bragged about appearing on a magazine cover. He supposedly told Daniels she was "perfect" for the cover because she's "a smart businesswoman" and that "people would think [she's] just this idiot with blond hair and big boobs." He mentioned his wife, Melania, in passing, Daniels claimed, but lauded his daughter, Ivanka, at length, even saying that Daniels was "beautiful and smart just like [Ivanka]." Daniels said "nothing crazy" happened between the sheets but that she "can definitely describe [Trump's] junk perfectly."

During the 2016 presidential race, Daniels couldn't describe anything about Trump's anatomy, per NBC, because Trump's fixer and personal attorney, Michael Cohen, paid her $130,000 for a non-disclosure agreement. He also arranged a $150,000 payment to former Playboy playmate Karen McDougal, with whom Trump allegedly had a separate affair. The attorney testified under oath that Trump ordered him to buy the women's silence to influence the election, so a court handed Cohen a three-year prison sentence for violating campaign finance laws. Now free to speak, Daniels described Trump's junk in a tell-all: "It has a huge mushroom head. Like a toadstool." Building on that imagery, she writes that Trump has a "d*ck like the mushroom character in Mario Kart." 

Citing years of IRS tax transcripts, the New York Times reports that between 1985 and 1994, Donald Trump's businesses lost over $1 billion. According to ThoughtCo, between 1991 and 2009, six of Trump's businesses went bankrupt. Those sorts of financial difficulties made it hard for Trump to obtain loans from Wall Street banks, which were averse to the so-called "Donald Risk," per Business Insider. However, he has secured an estimated $2 billion in loans from Deutsche Bank since the 1990s, and according to Donald Trump Jr., a substantial amount of money has come from Russia.

While speaking at a 2008 real-estate conference, Donald Jr. told attendees, "In terms of high-end product influx into the US, Russians make up a pretty disproportionate cross-section of a lot of our assets." And according to golf reporter James Dodson, Trump's son Eric said that the family's golf courses are funded by Russian money to the tune of $100 million. Dodson quoted Eric as saying, "We have all the funding we need out of Russia." These comments raised eyebrows in light of Russian interference in the 2016 presidential election. While Trump has repeatedly and vehemently denied having any business dealings with Russia, a 2017 Reuters investigation uncovered "that at least 63 individuals with Russian passports or addresses have bought at least $98.4 million worth of property in seven Trump-branded luxury towers in southern Florida."

In August 2019, President Donald Trump claimed "any Jewish people that vote for a Democrat" display "either a total lack of knowledge or great disloyalty." It was the latest in a list of inflammatory statements by Trump that some consider anti-Semitic. In 2015, the Times of Israel wrote then-candidate Trump invoked "offensive stereotypes" when he told a group of Jewish Republicans, "I'm a negotiator like you folks were negotiators," before asking, "Is there anyone in this room who doesn't negotiate deals?" In April 2019, he raised eyebrows while addressing Jewish Republicans when referred to Israeli leader Benjamin Netanyahu as "your prime minister."

Not long after his "disloyalty" remarks Trump retweeted comments by right-wing radio host Wayne Allen Root, who insisted "the Jewish people in Israel love [Trump] like he is the King of Israel. They love him like he is the second coming of God ... But American Jews don't know him or like him." According to the New York Daily News, internet users observed that Jews don't believe in a "second coming of God" and the phrase "King of Israel" was used to taunt Christ before his crucifixion. 

Root isn't alone in praising Trump's relationship with Israel. Media Matters reports that Fox News host Jeanine Pirro, who has previously advocated jailing Trump's critics, agreed to keynote "Jexit," a fundraising event geared toward convincing Jewish Democrats that Donald Trump "is the greatest friend to Israel and the Jewish people."

Donald Trump's brand has long been synonymous with immense wealth. It's so integral to his image that when author Timothy O'Brien wrote that Trump, a self-professed billionaire, was actually worth "between $150 million and $250 million," the Apprentice star tried to sue O'Brien for $5 billion, per ProPublica. In 2007, Trump insisted that by a "conservative" estimate his wealth totaled $4 billion. In 2011, he said $7 billion, and in 2016, he said his wealth exceeded $10 billion. But according to former Forbes writer Jonathan Greenberg, Trump has boasted a fake fortune for decades.

In 2018, Greenberg asserted that during the 1980s, Donald Trump assumed the alias John Barron and fed him "outright fabrications" in order to get onto the Forbes 400 list of richest Americans. The not-yet-president didn't make "vain embellishments on the truth," says Greenberg, but instead adopted what became a trademark tactic: "telling a lie so cosmic that people believed that some kernel of it had to be real." Greenberg provided receipts for his claims in the form of recorded conversations. 

The Washington Post notes that in 1990, Trump admitted under oath that he used the pseudonym John Barron "on occasion." He was embroiled in a lawsuit after hiring undocumented Polish migrants and allegedly threatening them with lawsuits under the guise of Barron to deter the workers from pursuing back pay.

Former Fox News personality and founder of TheBlaze Glenn Beck isn't afraid to speak his mind about presidents or change his mind about them. When Harvard Professor Henry Louis Gates was arrested in 2009 while trying to enter his own home, then-President Barack Obama said police "acted stupidly," and Beck branded the commander-in-chief "a racist" with a "deep-seated hatred for white people." In 2016, he changed his tune, saying Obama "made [him] a better man," per the Washington Post. At that point, Beck strongly opposed Donald Trump. But by 2019, he was hailing the 45th president as one of the last bastions of masculinity.

On his Blaze TV show, Beck lamented, "There are no examples of men being men. James Bond. That's it. A movie. There's no male role models ... So Donald Trump: here's a guy who marries a supermodel, is like, 'Yeah, I can make it with any model I want.'" Beck further explained that the Trump "is almost the cartoon of an alpha dog" and makes other guys go, "Damn right!" Numerous internet users took issue with Beck's assessment because of troubling allegations surrounding Trump. Per Business Insider, as of June 2019, 24 women have accused Trump of rape, sexual harassment, groping, and other offenses. Moreover, the infamous Access Hollywood tape features a conversation in which Trump bragged about grabbing women by the genitals without warning.

Donald Trump has faced allegations of racism since the 1970s. Per the Atlantic, the U.S. Justice Department sued Trump Management Company in 1973 and again in 1978 for denying apartments to people of color, whose applications were labeled with a "C" as part of the screening process. DOJ lawyer Elyse Goldweber recalled Donald Trump commenting, "You know, you don't want to live with them either." Trump's former construction manager, Barbara Res, remarked that Trump believed "blacks were lazy, and Jews were good with money" among other stereotypes. 

Since then, Trump has called for the execution of five black and Latino teens who were falsely accused of rape, paid a $25,000 fine after funding ads that portrayed Native Americans as drug dealers, and pushed the Birther narrative that Barack Obama wasn't born in the U.S. Against the backdrop of such incidents, Trump raised eyebrows in August 2017 after declining to overtly condemn white supremacists who marched in Charlottesville, one of whom murdered counter-protester Heather Heyer. In November 2017, Trump retweeted videos purporting to show Muslims murdering a person, destroying a statue of the Virgin Mary, and someone attacking a disabled teenager. Time explains that those clips came from the deputy-leader of Britain First, an ultra-nationalist group which gained prominence after a supporter murdered a UK lawmaker. Former KKK leader David Duke applauded the retweets, writing, "Thank God for Trump! That's why we love him!"

In 2018, the New York Times dropped a bombshell op-ed by an anonymous writer claiming to be a "senior" Trump administration official. The author, whose identity remains a mystery as of this writing, described a secret resistance consisting of political conservatives who operate under the radar to undermine Trump. The author alleges that "many of the senior officials in [Trump's] own administration are working diligently from within to frustrate parts of his agenda and his worst inclinations." 

The piece additionally paints the POTUS as a man with problematic policies and authoritarian tendencies, stating, "In addition to his mass-marketing of the notion that the press is the 'enemy of the people,' President Trump's impulses are generally anti-trade and anti-democratic." According to the author, "The root of the problem is the president's amorality." President Trump hit back, calling the op-ed "really a disgrace," per CBS. He later suggested that it constituted treason, tweeting, "Treason?"

In the immediate aftermath, Republican politicians rallied around the president, and Newsweek reports that Senator Rand Paul advocated forcing White House officials to undergo polygraph tests to root out the op-ed writer. Vice President Mike Pence voiced his unreserved willingness to take lie detector test, reportedly telling Fox News he would do it "in a heartbeat." However, the White House denied entertaining the idea of polygraphs.

Politico writes that among former presidents, there's an "unwritten rule of not undermining the current commander in chief." However the 45th president's predecessors have felt compelled to break that rule. Bill Clinton said of Trump, "He doesn't know much. One thing he does know is how to get angry white men to vote for him." In 2017, George W. Bush issued what many viewed as a rebuke of Trump during a speech in which Bush stated, "We have seen our discourse degraded by casual cruelty ... We've seen nationalism distorted into nativism." In 2019, Barack Obama condemned "leaders who demonize those who don't look like us, or suggest that other people, including immigrants, threaten our way of life." And Jimmy Carter turned heads when he questioned the validity of Trump's presidency altogether.

During a 2019 panel at the Carter Center in Virginia, Jimmy Carter remarked, "I think a full investigation would show that Trump didn't actually win the election in 2016. He lost the election, and he was put into office because the Russians interfered on his behalf." According to Time, Trump secured 304 Electoral College votes compared to 227 for Hilary Clinton while Clinton won the popular vote by a margin of 2.8 million people. However, as detailed in the Mueller Report, Russian operatives staged pro-Trump rallies and launched cyber attacks against the Clinton campaign.

The Mueller investigation's findings about the 2016 election are too intricate to recount in detail, but ABC provides a useful overview of how it all started. Aspects of the case date back to 2013, when suspected Russian spies discussed attempting to recruit Carter Page, "who years later would become an unpaid adviser to Trump's campaign." In 2016, Michael Flynn joined the Trump team months after receiving $45,000 to attend a Moscow gala for a pro-Kremlin TV network. Per FactCheck.org, Justice Department filings show that the Trump campaign's foreign policy adviser, George Papadopoulos, triggered the FBI's investigation after he informed a professor that Russians had stolen thousands of Hillary Clinton's emails and wanted to meet with the Trump campaign, which Papadopoulos wanted to arrange.

As described in the Mueller report, "The investigation did not establish that members of the Trump campaign conspired or coordinated with the Russian government." However, various individuals who were interviewed, including members of Trump's campaign, "deleted relevant communications or communicated during the relevant period using applications" that don't retain long-term records. Trump decried the investigation as a "witch hunt" and an unlawful "attempted coup." During Senate testimony, Attorney General William Barr appeared to bolster Trump's claims. When asked if he believed the FBI spied on the Trump campaign, Barr replied, "I think spying did occur." However, FBI director Chris Wray contradicted that claim, noting that the FBI conducted "court-approved" surveillance of the Trump campaign.

The hotly anticipated Mueller Report was littered with quotable passages. Many of them concern actions by Trump that some have construed as obstruction of justice. Per the report, Mueller's "investigation found multiple acts by the President that were capable of exerting undue influence over law enforcement investigations, including the Russian-interference and obstruction investigations. The incidents were often carried out through one-on-one meetings in which the President sought to use his official power outside of usual channels." These incidents included attempts to curtail the scope of the investigation, urging then-Attorney General Jeff Sessions to un-recuse himself from the case so he could quash the investigation, and attempting to sway witness testimony, and allegedly pressuring White House counsel Don McGahn to fire the special counsel Robert Mueller.

According to the Associated Press, McGahn's refusal to follow Trump's orders may have saved the latter's presidency from impeachment. In 2017, the White House counsel reportedly planned on resigning rather than can Mueller. He's quoted as telling then-White House Chief of Staff Reince Priebus that Trump wanted him to "do crazy sh*t." But McGahn stuck around a bit longer, finally resigning in 2018.

When Donald Trump tapped Rex Tillerson for Secretary of State, the former Exxon Mobil CEO seemed less than enthusiastic. In March 2017, Tillerson admitted, "I didn't want this job. I didn't seek this job. My wife told me I'm supposed to do this." Before long, Trump's enthusiasm began to wane as well. Though he had initially praised Tillerson as "a world class player" and "one of the truly great business leaders of the world," the president didn't always see eye to eye with him. When Tillerson tried to negotiate with North Korea, Trump dismissed talks as "a waste of time." When Trump faced backlash for statements about a deadly white supremacist march in Charlottesville, Tillerson made a point of saying, "The president speaks for himself."

The dynamic between the officials appeared to deteriorate in October 2017 amid press reports that Tillerson referred to Trump as a "f*cking moron." According to NBC, eyewitnesses said it happened after Trump pushed for "a nearly tenfold increase in the U.S. nuclear arsenal," which would have violated international nuclear nonproliferation treaties. The following month, the New York Times broke the news that the State Department head was on the chopping block. In March 2018, Tillerson got the ax. While the ex-secretary laughed off reports of the moron comment as "petty nonsense," he did say that Trump made demands which "[violate] the law."

Over his 33-year career as a late night jokester and interviewer, David Letterman welcomed Donald Trump as a guest more than 30 times. ABC reports that people have pored over those interviews in search of politically damaging info about Trump. Opponents latch on to a 1987 segment in which Letterman asks if the businessman was worth a billion dollars, to which Trump replies, "Perhaps," before refusing to get into specifics. 

However, Letterman doesn't see traces of the future POTUS in that interview. "There he seemed like a guy," said the host in In 2019. Speaking with the Hollywood Reporter's  "Awards Chatter" podcast, the late night icon described how that guy differed from Trump as president: "I think he just liked being on TV. I had no sense that he was the soulless bastard that he's turned into." Not yet done tearing into the president, he added, "He used to be kind of like the boob of New York that pretended to be wealthy, or we thought was wealthy, and now he's just a psychotic." If given the chance to ask Trump one more question, Letterman would choose, "When did you become a goon?"