If you didn’t know who Miles Taylor was before this conversation, that was the point at one time. He authored the 2018 NYT op-ed under the pen name “Anonymous,” detailing resistance efforts within the first Trump administration. The lifelong Republican was a political appointee during the George W. Bush administration and eventually become chief of staff for the Department of Homeland Security secretary under the first Trump administration.
Taylor revealed himself as the author of the op-ed and follow up 2019 book in 2020. In April 2025, President Trump signed a memorandum that ordered an investigation into Taylor for treason. His lawyers filed formal complaints with the inspectors general within the DOJ and DHS, asking them to investigate if the order violates the law and his constitutional protections.
It’s hard to know exactly what will happen when we have a live chat with someone we’ve never personally talked to. We knew our conversation with Miles Taylor would be lively, but I don’t think either of us had multiple Donald Trump impersonations on our Bingo cards.
Nothing was off limits in this conversation. We talked about Taylor’s initial concerns working for Trump 1.0, what’s different in Trump 2.0, retribution for even associating with dissenters and more. Taylor gives us an in-depth view of life in Trump’s crosshairs, his fears about the potential use of sophisticated counterterrorism technology against political foes, and why he thinks Elon Musk has the power to stop political retaliation.
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