Former New York City Mayor Michael Bloomberg is considering challenging President Donald Trump in the 2020 election, running as a Democrat against his fellow member of the billionaire’s club.
The 76-year-old would be the oldest and richest person to seek the Oval Office, New York City’s CBS affiliate reports.
This also marks the fourth time Bloomberg has mulled throwing his hat into the presidential ring – an option he considered in 2008, 2012, and 2016.
Bloomberg considered running as an Independent last cycle, but sources told CBS that if he runs in two years it would be as a Democrat.
Michael Bloomberg is considering challenging President Donald Trump in the 2020 election, running as a Democrat
President Trump and Michael Bloomberg are both New York billioniares
The move is fueled partly by regret that he didn’t stay in the race in 2016, because he feels he could have either won or at least prevented Trump from winning, a source close to former mayor told the news station.
Bloomberg opted not to run two years ago amid fears he could not win on a third-party line.
But he campaigned against Trump, who smacked him down as a ‘little guy.’
Despite being New York billionaires, the two men rarely spent time together.
In 2007, when Bloomberg was in the second of his three terms as mayor, the two played together in a charity event at Trump National Golf Club.
And Bloomberg appeared twice on Trump’s reality TV show, ‘The Apprentice,’ in 2004 and 2008, to show support for a program produced in New York.
Additionally, Bloomberg’s daughter Georgina is friends with Ivanka Trump.
There have been some hints Bloomberg is revving up for 2020.
The billionaire has already committed to spending at least $80 million to help Democrats win Congressional races this year and that will earn him a lot of political gratitude in the process.
He also hinted at his thinking on June 6, when he was honored at a YMCA fundraiser at Cipriani 42nd Street.
At the end of his speech Bloomberg told the crowd, ‘Before you leave I want to get your cellphone number because I’m thinking of getting the band back together,’ a source told the New York Post.
The guests erupted into thunderous applause, believing Bloomberg was hinting at challenging Trump.
In his May philanthropy report, Bloomberg’s opening letter appeared to be a thinly veiled rebuke of the Trump administration and its embrace of ‘alternative facts.’
‘There has always been spin in politics, but this is different,’ Bloomberg wrote, according to Forbes. ‘Disdain for facts is making it harder for America to address major challenges here and around the world.
And, in July 2017, Bloomberg, in an interview with the German magazine Der Spiegel, took a shot at Trump’s wealth, implying the president wasn’t actually a billionaire.
‘Let me phrase this carefully so you get the message: I don’t know how wealthy other people are,’ Bloomberg told the interviewer when asked about the president.
And when asked if he was implying Trump wasn’t a billionaire, Bloomberg replied: ‘I didn’t say that. You said that.’
Mayor Michael Bloomberg and Donald Trump during 20th Anniversary Gala for Vietnam Veterans at Vietnam Veterans Memorial Plaza in New York City
Mayor of New York City Michael Bloomberg attends the 16th Annual ASPCA Bergh Ball at The Plaza Hotel in April 2013
Bloomberg is believe to be worth $51.7 billion, according to Forbes, while Trump’s is believed to be $3.1 billion.
The former Mayor endorsed Hillary Clinton in 2016 and slammed Trump in a speech at the 2016 Democratic National Convention in Philadelphia.
‘Throughout his career, Trump has left behind a well-documented record of bankruptcies, thousands of lawsuits, angry shareholders, and contractors who feel cheated, and disillusioned customers who feel ripped off. Trump says he wants to run the nation like he’s run his business. God help us. I’m a New Yorker, and New Yorkers know a con when we see one,’ he said.
And Trump told CNN in January 2016 the friendship between the two men was over.
‘We used to be friends,’ he said when asked about Bloomberg’s criticism of him. ‘I guess we’re not friends anymore.’