Wake Up To Politics

Wake Up To Politics

What If... Trump Had Won in 2020?

And other reader questions.

Gabe Fleisher's avatar
Gabe Fleisher
Jun 29, 2025
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Hello (again) from the Aspen Ideas Festival! The newsletter is on a short pause while I’m here, but I still wanted to send out a Sunday Q&A issue, to make sure paid subscribers are still getting what you pay for! The full newsletter will be back on Wednesday.

In this morning’s mailbag:

  • How would things be different if Donald Trump had won the 2020 election?

  • What does Zohran Mamdani’s election tell us about politics nationally?

  • What exactly is a filibuster?

  • Where are we with Trump’s rescissions package?

  • Who picks the Senate Parliamentarian?

  • How big a change would it be if Lisa Murkowski switched parties?

Let’s get to the answers!

Q: What if Trump had won in 2020, and before the Supreme Court Presidential Immunity decision was made during that 2nd Term - how different (if any in your opinion) would a continuation of Trump 1 have been vs. the current Trump 2 version? Policies, Staff, Appointments, Federal staff and program cuts, his dealing with inflation, Covid, Ukraine, etc. Thanks.

Obviously, a political party should never try not to win a presidential race. But, in retrospect, the Democratic Party almost certainly would be better off today if they had lost the 2020 election.

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