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Winners & Losers | The Architect of Cruelty

Don Lemon & Tom Homan: A study in contrasts.

Sam Osterhout's avatar
Sam Osterhout
Feb 02, 2026
∙ Paid

I long for the days when RFK Jr. was the biggest loser of the week. Yes, his policies are making us sicker and putting our lives at risk. But he’s got a brainworm! He swam in raw sewage! He’s the kind of villain who does damage by bumbling through life, confident in his own genius because of his family name and his privilege.

Alas, we’re not there anymore. We have to keep our eye on RFK Jr., of course, but the the darker, more violent villains have stepped under the spotlight.



It’s been a little over a week since the killing of Alex Pretti. Maybe let that sink in a little bit. One week. That’s it. The response from the administration has been confusing, which is likely a result of their ineptitude plus their desire to make things, well, confusing.

This week’s Winner and Loser are flip sides of a coin that exemplify this moment in Trump’s war against America and one bit of the resistance building against it.

Let’s get started.

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Tom Homan, Loser

Tom Homan was raised with law enforcement coursing through his veins. His father and grandfather were both small town cops in Jefferson County, New York, near the Canadian border.

In 1983, he joined the West Carthage police force — the same department where his father and grandfather worked. But pretty quickly, his focus turned to immigration. In 1984, he joined what was then called the US Immigration and Naturalization Service, and he found his calling. ICE, coincidentally, wouldn’t exist for another couple of decades, almost.

Sometimes I forget that he worked for the Obama administration. In fact, it’s under Obama that he rose to real prominence. In 2013, he was named Executive Associate Director for Enforcement and Removal Operations at ICE — the No. 2 in charge. Obama personally awarded him a Presidential Rank Award for his effectiveness with deportations.

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