U.S. President Donald Trump speaks during a news conference at his Mar-a-Lago club in Palm Beach, Fla., Jan. 3, 2026. (OSV News/Reuters/Jonathan Ernst)
A friend sent me a recent "Letters from an American," the substack authored by Boston College historian Heather Cox Richardson. This particular entry focused on the horrific killing of Renee Good by Immigration and Customs Enforcement officer Jonathan Ross.
Richardson made the salient point that the administration released the video Ross had taken himself, thinking it was exculpatory, but for many Americans, it had the opposite effect. "Multiple social media users noted that Good's last words to Ross were 'That's fine dude. I'm not mad at you,' while his to her, after he shot her in the face, were 'F*cking b*tch!'" Richardson wrote.
Like most of Richardson's posts, this one is well written and makes some important points. Still, it is problematic. In both tone and content, it contained nothing that would persuade someone who voted for Donald Trump to regret their decision. Richardson's is a voice of an East Coast professor talking to other East Coast professors.
Instead of a highbrow historian from New England, the Democrats need to highlight someone who voted for Trump precisely because they were worried about unchecked migration across the southern border during the Biden administration, someone who will ask, "What does killing a citizen in Minnesota have to do with protecting our southern border?"
Or they could find a Southern police officer, the thicker the drawl the better, maybe even someone distantly related to Bull Connor, who will point out that, as a law enforcement officer, he was taught how to de-escalate conflicts with protesters and to always remember that he is charged with protecting the constitutional right to protest as well as public safety. The tagline: "What I saw on that video was a corruption of law enforcement."
Advertisement
Some may think it is churlish to be complaining about Democrats messaging ineffectively when a GOP-led ICE action left a woman shot to death. I get it. Outrage at ICE and Trump is entirely understandable. But Trump and Trumpism are political problems and the only way to prevent further tragedies like the one that unfolded last week is to defeat Trump at the ballot box. And that requires consciously reaching out to those voters who backed Trump because they were upset about inflation, even those who were worried about the effects of migration, those who likely recoiled when they saw the video of Good being shot.
Not all Democrats are afflicted with the inability to speak to somewhat conservative rural voters. James Pogue's essay in the New York Times highlights the "Blue Dog Democrats" like Rep. Marie Gluesenkamp Perez who has won a rural Washington state district that Trump also carried.
"Her central argument is that academics, economists and political consultants tend to fixate on a set of narrow, divisive issues that obscure what's really driving alienation and anger in our society today," Pogue writes. "That angst, for many, is about a basic worry that neither party is seriously listening to today: a fear that we are losing what the philosopher Henri Bergson once described as an 'open society' and replacing it with a society of the 'anthill' — with most people living a drone-like existence, reduced to data points in a system run by technocrats and corporations. It's a way of life that's anathema to both America's economic promise and its cultural traditions."
I do not have much confidence that the Democratic Party will get its act together. They may win the midterms because it is hard to lose a midterm election when the other party controls the White House and the Congress. In order to win a national election in 2028, or to retake the Senate in the near future, the Democrats need to start winning in flyover country. They need to step away from the cultural extremism they have embraced in the past 10 years and the language that accompanies it. Their theme must be that Trump corrupts everything he touches. His failure to release the full Epstein files is corrupting our Department of Justice. His crony capitalism, threatening to block ExxonMobil from Venezuela because he didn't like something the company's CEO said at a White House meeting, corrupts the free market. Trump's efforts to get states to redraw congressional maps corrupts the electoral process, allowing politicians to pick their voters rather than the other way round. These are corruptions that lifelong Republicans should detest as much as Democrats.
The text for political messaging and commentary in our badly divided country must become: Does what I write help unite the country around the better angels Trump is determined to eliminate?
You are reading a selection from Michael Sean Winters’ weekly newsletter. To get the full edition — including the "In the News" link roundup — delivered 24 hours before it's published online — sign up here.