How Donald Trump sneaked up on me and a bunch of new friends in Milwaukee

At the Republican National Convention in Milwaukee, the kindness and good nature of the local denizens were much talked about by attendees. But there was something else in the air: A new kind of openness to Donald Trump. 

I spent a lot of time outside the security perimeter, or ‘zone,’ as it was locally known, because I generally prefer talking to people who aren’t wearing lanyards and credentials for my work.

I stopped by the Milwaukee Brat Bar near the RNC entrance a few times, mainly because they have a cigarette machine, and my vice of choice was hard to find in the area.

There, one afternoon, I was getting change and I heard a man and a woman talking. They were in their thirties, nice looking. I couldn’t tell if they were a couple, coworkers or friends. And then I heard her say, ‘It’s like I’m coming around to Trump.’

For me, this kind of comment was like a ’49er striking gold, so I politely introduced myself and inquired if I might I ask them a few questions.

I wanted to know when this softening of attitude towards the former president had started. She wasn’t sure. She thought it had been gradual, but that the July 13 assassination attempt on Trump had built on it. As for the guy, he told me he had not voted for Trump in 2016 or 2020. I asked if he had been open to it back then, and he said no. And in ’24? Yes, he was now.

It didn’t seem policy driven, or even the ‘are you better off than you were four years ago?’ thing. It was more like finding a way to tolerate an annoying member of your friend group. Trump was no longer a dealbreaker for a dinner party invitation.

The next day, grabbing lunch at Who’s on Third, I met Jay and Jeff, who are both very committed Trump supporters. Jay, in advertising and in his fifties, had been coming down to the zone for lunch every day to dig the goings on.

Their enthusiasm was high. Both thought the iconic image of Trump pumping his fist after getting shot was a game changer. They almost seemed giddy at the prospect of a second Trump term.

One question I have asked strong Trump supporters over the years is whether the people they work with know how the feel about him. Both Jeff and Jay said they weren’t shy about it now, but acknowledged they used to be. I hear that a lot.

Trump just isn’t taboo anymore, and one has to wonder if that might be part of why Joe Biden is no longer in this race.

My most personal acquaintance with Milwaukee kindness came one evening when my friends stranded me. I had been to dinner, and told my crew prior to dinner to let me know when they were heading back to the hotel. After dinner, I texted ‘where are you?’ 

They were at the hotel. 

It wasn’t the end of the world. I’d take an Uber, but I was out of cigarettes and went back into Brats. There I met Scott and Lizzie, a married couple who looked like they belonged in a Williamsburg, Brooklyn, electroclash night club in 2004, not like the RNC cats at all.

But they were Trump supporters, so we got to talking and I told them my story. That’s when Scott glanced at an approving Lizzie and they offered me a ride.

In a very Northeast way I said, ‘I can’t ask ya to do dat, it’s a half hour.’

He said, ‘You’re not asking, we’re offering.’  And I said, ‘You know what? Ok.’ I think it was the most Midwestern thing I’d ever heard uttered.

On the way back to the hotel, an incredible thunderstorm rattled giant flashes of lightning that dominated the skies. This truly was the flat and honest middle of America. We chatted about our kids, the amazing joy and challenge of all that. We also played a game I invented back in the 90s based on the sitcom ‘Friends.’ Lizzie won.

But politics did come up, and it turned out all three of us had had a slow acceptance of Trump. We talked about how his newly minted running mate, JD Vance, had been a Never Trumper. It seemed like all of us, or at least most of us, had been. Fully embracing him was so new, and so crazy, we agreed. But it was also a natural evolution many people have gone through. 

I told them a story about the night of the election in 2016 when I asked a mentor of mine, ‘What do we do now?’ And he said, ‘You call balls and strikes. He does something you like – say so, something you don’t like – say so.’

Lizzie, Scott and I all agreed there was more that we liked than we didn’t.

When I got back to the hotel and told my friends what happened, one said it was the most Dave Marcus story ever, and maybe so. But it’s really just an American story. I’ve gotten plenty of rides from strangers in Texas, California, and a million other places because we liked each other. 

But I felt something new in Wisconsin. Trump just isn’t taboo anymore, and one has to wonder if that might be part of why Joe Biden is no longer in this race.