Brewer’s Winners and Losers: ‘It Almost Looks Like Working for Governor DeSantis Might Be Difficult’

Aug 10, 2023

Political watcher and recovering journalist Clint Brewer joined host Michael Patrick Leahy in-studio on Thursday’ episode of The Tennessee Star Report to discuss this week’s ‘Winners and Losers.’

Topping the ‘Winners’ list was Metro Councilman Freddie O’Connell while 2024 presidential hopeful Ron DeSantis was tapped for top spot on the ‘Losers’ list.


Michael Patrick Leahy: Well, Clint, who do we have as a winner this week?

Clint Brewer: Well, it’s obvious – we’ve already talked about him. Councilman Fred O’Connell.

Michael Patrick Leahy: Obvious.

Clint Brewer:  Obvious.

Michael Patrick Leahy: 27 percent finished – first place.

Clint Brewer:  Yeah.

Michael Patrick Leahy: Odds-on favorite, probably, to win and become the next man

Clint Brewer:  Yeah – based on reliable polling going into the contest with a pretty commanding lead.

Michael Patrick Leahy: Although I’ll have to say Alice Rolli ran a very good campaign and look: if she can turn out people that didn’t vote before, she’s got a shot.

Clint Brewer: Yeah; Or, she can put this in her back pocket if she loses, and maybe she runs for something else.

Michael Patrick Leahy: Maybe.

Clint Brewer: Maybe.

You never know.

Michael Patrick Leahy: You never know. But I do think Freddy O’Connell is the winner of the week at, that’s obvious.

Clint Brewer: Absolutely. Absolutely.

Michael Patrick Leahy: Now, let’s turn the page.

Who, Clint, is the loser of the week?

Clint Brewer: Well, I mean, there are a lot of them.

Michael Patrick Leahy: There are many. They’re – let me just stop.

Clint Brewer: They’re a legion.

Michael Patrick Leahy: America in 2023: a lot of losers there.

Clint Brewer: Yeah, right. I mean, it’s a deep bench.

Iowa’s getting geared up. He’s just squandered his opportunity. I’m not saying he’s done, but–

Michael Patrick Leahy: Well, he’s on his third or fourth reboot.

Well, first, not to beat a dead horse, shall we say, but in the period from his great victory of like 19 points as governor in November – from that period – until the bizarre technologically flawed on Twitter launch of his campaign. That–

Clint Brewer: It’s been–

Michael Patrick Leahy: That was bad.

Clint Brewer: It’s been a comedy of errors.

Michael Patrick Leahy: And that now he’s just, you know, his leading Super PAC spokesperson was put on ice for telling the truth.

Clint Brewer: The European tour, the book tour, that didn’t seem to ever actually happen.

Michael Patrick Leahy: I mean, and now he’s fired his campaign manager. Yeah, it, it’s hard to see, you know, how he can–

Clint Brewer: It almost looks like working for Governor DeSantis might be difficult.

Michael Patrick Leahy: Yeah. It’s just; well, maybe. We’ll see.

Clint Brewer: Yeah.

Michael Patrick Leahy: But let’s say if we were to give Governor DeSantis some advice right now – he’s only what, 45, 46? He’s a young guy.

So my advice to Governor DeSantis would be: pack it in, brother, and focus on being a governor and you know, whoever the GOP nominee is – looks like it’s gonna be Trump – back him and then keep your powder dry until 2028.

Clint Brewer: Right. I agree with you.

I mean, I don’t know if I would completely withdraw, but he’s got to find somebody he’ll listen to.

He needs somebody who’s done this before who has the perspective on how to run a national campaign. And his people – I mean, maybe he’s had that in his cadre of advisors and he just won’t listen to them?

That’s what it feels like to me.

Michael Patrick Leahy: I think your sense and your feeling about his campaign and his structure of his campaign and his staff – I think that’s right.

I’m hearing multiple sources say – let’s just say the nicknames that I give to those who, you know, I’m not favorably inclined towards – those nicknames are used to describe his entire staff.

Clint Brewer: Yeah. And  that’s the thing–

Let me say this correctly. I’ve got it in my head. I need to get out of my mouth.

The things he’s getting wrong are the things that are very easy to get, right?

Michael Patrick Leahy: Yes.

Kind of in the category of–

Clint Brewer:  He’s screwing up the easy stuff.

Michael Patrick Leahy: Unforced errors.

Clint Brewer: I mean, they’re just schedules and staff and – you know how you do it. There are templates for these things.

Michael Patrick Leahy: Pace.

And the other thing is – and this is sort of my complaint of all of the Keebler Elves.

I think we’ll use that, we’ll give a hat tip to Steve Bannon for that term – other than Vivek.

They just, so 1990s in the way they approached the campaign: ‘Okay wah, wah, wah, here we go; a press conference on this.’

In contrast, I’ll say this: Vivek? Man, that’s a guy constantly in motion, constantly pushing, constantly hitting issues that others won’t.

But he came down here last week and called for the release of the Covenant Killer Manifesto.

A good move on his part.

Clint Brewer: He seems to have more of the cadence And the understanding of the pace of a modern campaign.

Michael Patrick Leahy: You nailed it: cadence and pace. And what they do is – I mean, because he’s a half-a-billionaire.

He’s got a private plane. I don’t know if he leases it or owns it, but he flies around.

He’s, he’s in Iowa today; he’s in New Hampshire tomorrow; he’s in Nashville – every day he does something, right?

And also very articulate, and in the course of a week, he’ll have two or three major policy issues that he makes statements on; and the way he does it very quickly – he has a video on his plane, he’ll do a three or four minute video posted – boom – that makes headlines – boom.

And so he has the cadence and the pace that are appropriate for the kind of fast-moving, social-media-driven environment that we live in today.

Clint Brewer: Well, and I think he seems to be doing well on the ground in Iowa, which is a retail political environment as you’ll ever be in.

Michael Patrick Leahy: Unlike Ron DeSantis, he actually likes people; and people like him.

And again DeSantis is a good guy, but very stiff.

And on that note, Clint Brewer – Clint “The Man” Brewer – thanks for joining us today.

Clint Brewer: Thanks, Mike.

Michael Patrick Leahy: We’ll be back with Roger Simon after this.

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Tune in weekdays from 5:00 – 8:00 a.m. to The Tennessee Star Report with Michael Patrick Leahy on Talk Radio 98.3 FM WLAC 1510. Listen online at iHeart Radio.
Photo “Ron DeSantis” by Ron DeSantis.