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Kevin Sheekey always speaks with a sense of urgency. Usually, he does so as a happy warrior in pursuit of the goals of his boss, former New York City mayor Mike Bloomberg. But now Sheekey’s the campaign manager of Bloomberg’s 2020 quest for the Democratic nomination for president, and there is the sound of genuine fear in his voice.

In the worlds of politics and political journalism, Sheekey is like Cher, widely known by one name and just as famous. He is part of the small and tight coterie of advisers who have guided Bloomberg since before he ran for mayor in 2001. Full disclosure: I worked on that campaign as a policy adviser after being approached to do so by Sheekey. So, when I tell you there was something different about his tone, trust me.

Before the mics were even set up for the interview in a small office at Bloomberg campaign headquarters on Manhattan’s Upper East Side, Sheekey told me, “President Trump is already winning and Democrats don’t even realize it.” When I asked him to elaborate once we were recording, Sheekey didn’t hold back.

“As we’ve seen the polls in the swing states, I’m incredibly nervous. I am nervous that Donald Trump is poised to win again,” Sheekey told me in the latest episode of “Cape Up.” “And quite frankly, there’s no question in my mind that Brad Parscale, who is Donald Trump’s campaign manager, shows up for work in the morning and thinks he has a winning hand, and that he’s playing a winning hand.”

According to Sheekey, that winning hand manifests itself in the different ways Trump and the Democrats are campaigning. And that explains why Bloomberg is embarking upon a multi-pronged, never-tried-before strategy. He is skipping the first four contests in Iowa, New Hampshire, Nevada and South Carolina in favor of garnering support in contests later on the calendar, including the 16 Super Tuesday states, territories and so-called Democrats Abroad that vote on March 3.

“As a party, we’re running a primary to pick a party nominee and Donald Trump is running a general election, and they’re happening in two different places,” Sheekey said. While Democrats are investing in winning the four early contests, Trump is waging a general-election campaign in the six states Sheekey said will decide the 2020 election: Arizona, Wisconsin, Michigan, Pennsylvania, North Carolina and Florida.

“If we really wanted a primary that would give Democrats an advantage and ultimately, in my view, a winning advantage,” Sheekey explained, “you would restructure the primaries so that the first state would be Wisconsin. Second state would be Michigan, third state would be Pennsylvania, the fourth state would be Florida.” He later remarked that the current Democratic primary system “runs an enormous risk of both ceding all of this year to Donald Trump in places that matter in November, and investing all of our resources in places that don’t.”

“I think that you can run a national campaign. Now, no one has run a national campaign for a primary in my view since 1960 and John F. Kennedy,” Sheekey noted, “but my view is if there was ever a time to run a national campaign and get people all around this country involved and organizing and knocking on doors and standing up for the need to replace this president, it’s now.”

I’ve neglected to mention that Bloomberg is a multi-billionaire who is not only using his personal fortune to bankroll his presidential campaign. He’s also using it to do things that are vital for the Democratic Party, no matter who the 2020 nominee ends up being.

“We’re not only running digital ads around the country and in Super Tuesday states on Mike’s behalf, we’re running ads against the president right now in the upper Midwest, Wisconsin, Michigan, Pennsylvania, and we’ll stretch that to 10 other states,” Sheekey said. “Mike has started the general election now on behalf of Democrats and, again, is doing things that are not designed to benefit his candidacy but are meant to weaken the president, so when there is a nominee, we can replace him.”

Listen to the podcast to hear Sheekey talk more about the campaign’s strategy. We talk about Bloomberg’s mayoralty, including “stop and frisk.” And I asked him why he thought the controversial police tactic hasn’t stopped some prominent African American mayors such as Michael Tubbs of Stockton, Calif., and Steve Benjamin of Columbia, S.C., from supporting Bloomberg. “Really good mayors make mistakes all the time, and you know why? Because they do things,” said Sheekey. “You know who doesn’t make mistakes? People that don’t do anything.”

Running for president is the ultimate thing to do for Bloomberg. And mistake or not, whether Bloomberg is the Democratic nominee or just laying the groundwork for that person to beat Trump in 2020, Sheekey wants everyone to know something. “Mike Bloomberg is in this race to put a few nails in Donald Trump’s coffin as president of the United States.”

“Cape Up” is Jonathan’s weekly podcast talking to key figures behind the news and our culture. Subscribe on Apple Podcasts, Stitcher and anywhere else you listen to podcasts.

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