If you’re a Democrat, how worried should you be right now? It’s strangely hard to answer that question. On the one hand, polls suggest Democrats should be very worried. President Biden looks weaker than he did as a candidate in 2020, and in matchups with Donald Trump, the election looks like a coin flip. On the other hand, Democrats staved off an expected red wave in the 2022 midterm elections. Biden has a strong record to run on, and Trump has a lot more baggage than he did in 2020. So, in an effort to put all those pieces together, I had two conversations with two people who have polar opposite perspectives — starting with a more optimistic take for Democrats. Simon Rosenberg is a longtime Democratic political strategist, the author of the newsletter Hopium Chronicles and one of the few people who correctly predicted the Democrats’ strong performance in 2022. He argues that the Democratic Party is in a better position now than it has been for generations. In this conversation, we talk about why he isn’t worried about Biden’s polling numbers, how anti-MAGA sentiments have become a motivating force for many voters, what he thinks about the shifts in working-class support of the Democratic Party, why there’s such a huge gap between Biden’s economic track record and how voters perceive the economy right now, how Biden’s age is affecting the campaign, whether his foreign policy might alienate young voters and more.