For Bloomberg — who has been a Republican, independent and Democrat — the staffers could be critical as the 76-year-old businessman navigates the modern Democratic Party, giving him links to blocs and stakeholders who may be wary of his past and politics.
Many of those advisers say that if Bloomberg does not enter the 2020 race, they plan to stay on his team anyway, working to build what one top aide described as a “Koch Brothers-type group for Democrats,” a digital and grass-roots powerhouse that would spend hundreds of millions of dollars with the sole mission of defeating President Trump.
The spate of high-profile hires and the establishment of a sweeping, data-heavy political operation underscore Bloomberg’s determination to shape the 2020 campaign, whether he decides to be a candidate or spends millions as an advocate and influencer, following a 2018 cycle in which he and his allied groups spent more than $110 million.
And it reflects mounting unease in Democratic ranks about the political cost of a protracted presidential primary cycle in which a number of contenders could battle until the Democratic National Convention. Such a fight could leave the party distracted, Bloomberg advisers said, necessitating that someone construct an outside political machine ready for fall 2020.
“Whether Mike runs or not, he really wants to advance the science of how you target voters,” Kevin Sheekey, a longtime Bloomberg adviser, said in an interview. “One of the country’s best technology entrepreneurs ever is going to make sure that whoever wins the Democratic nomination is going to all have the support they’ll need to win a general election and beat Trump.”
Sheekey declined to reveal how much Bloomberg has spent so far but said that “Mike has certainly spent more than anyone else has raised” in the emerging Democratic field.
According to Forbes, Bloomberg is worth more than $50 billion, making him one of the nation’s richest people.
One factor looming over Bloomberg’s decision is former vice president Joe Biden, who has leaned toward running but has not made a decision. Bloomberg advisers said Biden’s brand of politics is similar to the former mayor’s, so a bid by the former vice president could push Bloomberg to stay out of the race.
“Whatever the next year brings for Joe and me, I know that we will both keep our eyes on the real prize, and that is electing a Democrat to the White House in 2020,” Bloomberg said in January at the National Action Network’s Martin Luther King Jr. breakfast.
The Washington Post confirmed Bloomberg’s latest hires with several aides, some of whom were not authorized to speak publicly.
Joining his inner circle as a strategist is Mitch Stewart, who directed Obama’s triumphant Iowa caucus campaign in 2008. Brynne Craig, who has signed on as an adviser on political strategy, served on Hillary Clinton’s 2016 campaign and has connections with many party and constituency groups.
In some respects, Bloomberg’s campaign-in-waiting is an outgrowth of Everytown For Gun Safety, his organization focused on gun control that has been a political force in recent elections.
Bloomberg is working closely with Bully Pulpit Interactive, a marketing agency founded by Obama campaign veterans, to develop a national digital advertising and analytics operation. Dan Wagner, who was chief analytics officer on Obama’s 2012 campaign, is advising Bloomberg — and other hopefuls — on strategy.
The former mayor has recruited top talent especially in the early voting states. Matt Paul, who ran Clinton’s campaign in the 2016 Iowa caucuses, has signed on to advise Bloomberg in that state, though he’s not doing so exclusively. A onetime broadcast journalist and aide to then-Gov. Tom Vilsack, Paul has relationships throughout Iowa.
In New Hampshire, Bloomberg has hired Liz Purdy, a seasoned operative in the state, where she has worked for Democratic Sens. Jeanne Shaheen and Maggie Hassan. Purdy also helped steer Clinton’s campaign in New Hampshire’s 2008 primary.
On communications, Jason Schechter, who oversees communications at Bloomberg L.P., the financial information and media company founded by Bloomberg, is playing a key role, along with other media aides.
In recent weeks, a growing group of Bloomberg advisers has been holding private meetings in Manhattan near Bloomberg’s philanthropic headquarters, mapping out his schedule and discussing strategy. Bloomberg has purchased national voter files so his team can get an early start, one adviser said.
“The Trump campaign is extremely well-capitalized and the world is moving very fast from TV to online,” said one Bloomberg adviser. “Democrats need to make sure they have the tools to be at full velocity.”
Leading the sessions is a trio of Bloomberg advisers who have worked with him for years: Sheekey, Howard Wolfson and Patti Harris. All served as deputy mayors in his administration. Wolfson was a co-chief strategist on Clinton’s 2008 presidential campaign, and Harris is the chief executive of Bloomberg Philanthropies. Bloomberg’s longtime pollster Doug Schoen and media strategist Bill Knapp are also part of the team, according to three aides familiar with their work.
The Atlantic first reported that Bloomberg is planning to spend millions of dollars on a data and political organization, regardless of whether he runs for president.
Bloomberg’s commitment to Democratic causes, driven by his antipathy toward Trump, and his work on climate change and gun control in recent years, stands in sharp contrast to another billionaire who moved closer to a 2020 campaign this week: Howard Schultz, the former CEO of Starbucks, who is weighing an independent bid.
In a statement Monday, Bloomberg criticized third-party candidacies.
“In 2020, the great likelihood is that an independent would just split the anti-Trump vote and end up reelecting the president,” Bloomberg said. “Given the strong pull of partisanship and the realities of the electoral college system, there is no way an independent can win.”
Bloomberg traveled to New Hampshire this week, and last Friday he called Trump a “pretend CEO.”
“The longer we have a pretend CEO recklessly running this country, the worse it will be for our country,” Bloomberg told the Democratic Business Council of Northern Virginia.
Speaking in New Hampshire, Bloomberg cast himself as a centrist in comparison with others in the Democratic mix, such as Sen. Elizabeth Warren (D-Mass.), who has proposed a 2 percent annual fee on households with a net worth greater than $50 million.
“It probably is unconstitutional,” Bloomberg told reporters, explaining that he favored a more progressive income tax. “We shouldn’t be ashamed of our system.”
Philip Rucker contributed to this report.