"We can lose this election": What top Democrats fear could go wrong in 2020

“I think this is going to be a longer, more protracted primary fight and we’re going to have certainly weeks, if not months where we’ll be doing our primary and we won’t be talking to swing voters in, say, Tampa Bay,” warned Florida-based Democratic strategist Scott Arceneaux…

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“I think someone who’s not worried about the money is crazy. Trump’s sitting on $100m right now and we’re nowhere close to having a nominee and they will be able to raise money but we’re still so fractured,” said Democratic consultant Brandon Hall. “That worries me. I mean I don’t know how that doesn’t worry everybody, that we’re always going to be playing catchup on the money.”…

“On the digital side Trump’s digital operation is two things: smart and dangerous,” said Democratic strategist Jennifer Holdsworth. “It’s both. So I think that we are playing checkers and they’re playing chess in that particular lane of strategy and it’s something we are not going to wake up to until we’ve gotten past the primary and they are miles ahead in terms of messaging and we’re going to have to catch up.

That’s why, Holdsworth continued, Democrats needed to quickly rally around the eventually nominee “either before or immediately after the convention or we’re never going to catch up”.

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