Wake Up To Politics

Wake Up To Politics

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Wake Up To Politics
Wake Up To Politics
What If... Trump Had Won in 2020?

What If... Trump Had Won in 2020?

And other reader questions.

Gabe Fleisher's avatar
Gabe Fleisher
Jun 29, 2025
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Wake Up To Politics
Wake Up To Politics
What If... Trump Had Won in 2020?
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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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