And yet, Friday, though he was home in New York, Bloomberg aides filed the necessary paperwork to run in the Democratic presidential primary in Alabama, which has the country's first filing deadline.
Bloomberg and a host of others have been weighing whether to jump into the 2020 race because of the widespread concerns with the current field, with Democratic donors and activists anxious no one now running could beat Trump.
Bloomberg also has longtime connections in the state after funding several Democratic initiatives over the years.
Trump says there's "nobody" he'd "rather run against" than Bloomberg.
Bloomberg, the billionaire former mayor of New York City, decided in March he would not run for president, despite leaning toward it for months. Bloomberg left a voicemail indicating he plans to run.
A Fox News poll in late October found Mr Bloomberg faces more opposition than enthusiasm at the outset of the primaries.
In a follow-up email, Vilsack told the AP that Bloomberg said in the message that "it was true he is running".
Bloomberg, who initially ruled out a 2020 run, has not made a final decision on whether to jump into the race.
Vilsack was the US secretary of agriculture under President Barack Obama.
It also points to Biden's steady lead in SC and Nevada, the latter two of the four early state primaries, which have a far more diverse electorate than both Iowa and New Hampshire. He called Bloomberg a solid guy and said he has no problem with Bloomberg getting in.
"But Mike is increasingly concerned that the current field of candidates is not well positioned to do that", Wolfson said.
I suspect Bloomberg will not get far, if he actually takes the plunge.
If the DNC primary did not feature a stark contrast of ideology, between the more moderate Biden campaign and the progressive Sanders and Warren campaigns, Bloomberg would have most likely sat out of the 2020 primary.
For one thing, Trump only spent $66 million of his own money on winning the presidency - a large sum, but inconsequential in comparison with the $2.4 billion spent on the race in total.
In a joint statement Friday, New Hampshire Democratic Party Chair Ray Buckley and Iowa Democratic Party Chair Troy Price praised the "many qualified candidates" already in the race. He doesn't need voters to like him - he just needs them to hate Trump.
In an op-ed back in March for his Bloomberg News, he wrote: "I believe I would defeat Donald Trump in a general election".
"With regard to Michael Bloomberg, I welcome him in the race", Biden said.
Trump suggested Bloomberg would spend a lot of money and go nowhere.
However, Michael Gray, the chairman of the Arkansas Democratic Party, said Mr Bloombergs wealth could make him an important wild card in the race.
Billionaire former New York City Mayor Michael Bloomberg is opening the door to a 2020 presidential campaign.
The early states offer just a small percentage of the delegates needed to clinch the Democratic nomination.
Mr Bloomberg plans to skip early voting states like Iowa and New Hampshire if he launches a presidential bid and instead focus his efforts on the crush of states that vote on Super Tuesday and beyond.
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