Michael Bloomberg's recent past has threatened to derail his campaign to unseat Donald Trump in the White House, as the former mayor of New York's very public statements and lawsuits have illustrated his alleged sexism, support for racial profiling, transphobia, and – perhaps most damaging – his affection for the president.
Joe Biden targeted Mr Bloomberg in a campaign ad, sharing a 2011 clip of the billionaire saying, "I'm a friend of Donald Trump's. He's a New York icon."
But in another video, taken one month after Mr Trump's election in 2016, Mr Bloomberg says that he told the president-elect that he loves him and believes he's a "nice person".
Download the new Independent Premium app
Sharing the full story, not just the headlines
During an appearance at Oxford University, Mr Bloomberg fondly remembered a conversation with then-citizen Trump at a 9/11 memorial service.
He said Mr Trump told him that he saw his speech to the Democratic National Convention in Philadelphia, where Mr Bloomberg called the then-nominee a "dangerous demagogue".
Mr Bloomberg says that Mr Trump asked him, "But you really do love me, don't you?"
"And I said, 'Yes, Donald, I do love you, I just disagree with everything you've ever said'", Mr Bloomberg said.
"And we had a good laugh ... If you've sat and had dinner with Donald Trump, you'd probably walk away saying everything he just said is bulls*** ... But you have a good time. He is socially a nice person."
Facing pointed attacks from his Democratic rivals for his pay-to-play candidacy and past remarks ahead of his first debate appearance, Mr Bloomberg took aim at the field's top-polling contender, Vermont Senator Bernie Sanders, whom he accused of having a close affiliation to Mr Trump, dividing Democrats and relying on boorish campaign tactics – all of which Mr Bloomberg has been accused of in his multi-million dollar blitz for the presidency.
In response, Mr Sanders made his point by simply posting a photo of Mr Bloomberg and Mr Trump smiling together on a golf course.
Mr Bloomberg's campaign has tried to downplay his relationship with Mr Trump while both of them trade insults at one another on Twitter.
The former mayor addressed the president on Twitter saying: "We know many of the same people in NY. Behind your back they laugh at you & call you a carnival barking clown. They know you inherited a fortune & squandered it with stupid deals and incompetence."
Mr Trump called him a "loser" and a "mass of dead energy" in response.