The New York businessman fully embraced the persona: His eponymous building in Midtown Manhattan even strung up a large banner with the phrase as the show was just getting off the ground in 2004.
But deep down, Trump is a people-pleaser, his former employees and friends say, someone who abhors direct confrontation and would rather be well-liked by all, even if that means giving his aides power to ax people.
"I think Donald Trump doesn't like to fire people, period," the former House Speaker Newt Gingrich, a Trump adviser and friend, said Tuesday on Fox News.
During his presidential campaign and into his presidency, Trump has kept dismissals at arm's length, fuming in public at the state of his affairs, but rarely acting as the person who brings the hammer down on the person behind his ire.
Jeff Sessions, Trump's Attorney General and one of his earliest top supporters, is now feeling the impacts of Trump's distaste for firing people. Sessions is effectively an attorney general without the backing of his president, as Trump has tweeted in the last 48 hours that the former Alabama senator is "beleaguered" and "weak."
These traits have been on full display Wednesday as Trump tweeted criticism of Sessions as the Attorney General was inside the White House for what a source at the Department of Justice called a "routine meeting."
"Why didn't A.G. Sessions replace acting FBI Director Andrew McCabe, a Comey friend who was in charge of Clinton investigation but got big dollars ($700,000) for his wife's political run from Hillary Clinton and her representatives," Trump tweeted.
Another recent example of Trump avoiding a dismissal was when the President decided to fire FBI Director James Comey. Trump fumed about Comey behind closed doors, according to White House officials, but it was Trump's longtime body guard-turned-White House aide, Keith Schiller, who took a car to the FBI headquarters to deliver the news to Comey.
Trump's distaste for conflict also kept him away from some of his campaign's most public firings. When Corey Lewandowski was dismissed in June 2016, it was Trump's son -- Donald Trump Jr. -- who broke the news to the fired campaign manager. And when New Jersey Gov. Chris Christie was canned from the Trump transition shortly after Trump's win on Election Day, it was his top strategist -- Steve Bannon -- who told the governor.
The President's handling of Sessions has begun to draw the ire of his Republican colleagues, who have longstanding relationships with the former senator.
"I would fire somebody that I did not believe could serve me well rather than trying to humiliate him in public, which is a sign of weakness," Sen. Lindsey Graham, a South Carolina Republican, told CNN's Manu Raju on Wednesday. "I would just go ahead and say, 'I appreciate your service, you need to be fired.' "
Trump, according to longtime friends and White House officials, likes to act like he is a heavy when it comes to running his businesses. The President, in conversations between his staffers and people outside the White House, regularly asks how his staff is performing, joking that he will fire them if the answer is negative.
Trump did this publicly earlier this week when he joked in front of thousands of people at the Boy Scouts of America's National Jamboree in West Virginia that he would fire Health and Human Services Secretary Tom Price if he can't pass health care reform.
"He better get (the votes)," Trump said of Price, who was standing behind him. "Otherwise, I'll say, 'Tom, you're fired.'"
Price and Energy Secretary Rick Perry are seen laughing behind the President.
But that truly isn't Trump, and the businessman-turned-politician has admitted as much.
In an interview during his run with "The Apprentice" in Life Beyond Sport, a men's lifestyle magazine, Trump cast the perception that he likes to fire people as wrong.
"You mentioned how much you respect you have for the contestants in your show," the questioner asked. "It must be really hard to fire them. Do you ever have regrets about doing it?"
Trump said: "I have regrets. Sometimes I do. People think I enjoy firing people. I don't."
That view is backed up by his former employees.
Barbara Res, Trump's former head of construction, told CNN on Wednesday that she never saw Trump fired someone in 18 years of working with him.
"He didn't like to fire people but he didn't mind firing companies, like an architect or an engineering firm," she said. "But when it came to people who worked directly under him... just to fire you because you are no good was very hard for him."
Res recalled a story during the building of Trump Tower in New York, a project she oversaw for the businessman.
Trump, she recalled, hired a building manager that didn't mesh well with the other staff, so Res and her assistant told Trump that the guy needed to be fired. Trump agreed, but asked them to do it.
"We told him, 'That is it. We are going to let you go,' " Res said. "Anyway, the guy goes to Donald's office, goes across the street, and Donald says, 'OK fine, we will keep you.' "
Res said she was then "stuck" with him until, again, she got Trump's approval to fire him. After doing so, the building manager went back to Trump and got him to reverse the decision. The construction manager was eventually fired on attempt No. 3 -- by Res, not Trump.
"He loves to say everyone loves him, which is not the case. He likes to be buddies with people," Res said when asked about the lessons she learned about Trump during that back-and-forth. "I think that is part of it."