History repeats itself and unless we learn from it, we're going to make the exact same mistakes. Glenn asked on radio Tuesday what would happen if we could go back in time to 2008. Is there something more we could have done to reach Obama supporters and make a difference?

Think back to the Lewinsky scandal when Clinton supporters vehemently denied the scandalous accusations. "Doesn't matter," they would say---until it became evident he was guilty of sexual indiscretions. Then, they changed their tune.

Could we have tried harder to help Obama supporters understand why his history with Jeremiah Wright and Bill Ayers mattered? Should we do more now to help Trump supporters look at their candidate's stance on issues and ask, "Does it matter?"

That's a question that does matter.

Listen to the segment or read the transcript below.

Below is a rush transcript of this segment, it might contain errors.

GLENN: If we had to do it all over again, is there a way that we could have reached the Obama supporter and actually made -- had them look at things and say, "Okay. No wait a minute. Hang on just a second. You're right. Jeremiah Wright. Boy, that is disturbing." Is there a way that we could -- is there something we could have done that would have opened people's minds intellectually?

STU: I think what you're looking for here, if I'm understanding, is, is there that magical phrase? Is there that magical approach? Is there some tone change or something like that --

GLENN: Yes. Is there anything that we did that we now know -- because history repeats itself. So the next time you come across an Obama supporter, but it's a new Obama, how do you approach them? And we don't repeat the same exact mistakes.

Do you remember, Pat -- and this didn't work -- but remember during the Lewinksy thing, we said, "The question should have been at the very beginning, yes, okay -- because what happened was, he didn't do it. Yes, he did. No, he didn't. Yes, he did. No, he didn't. Yes, he did. He did it. Doesn't matter. He did it. Doesn't matter. He did it. Doesn't matter.

Wait a minute. What? You've been arguing with me for six months that he didn't do it. And you were calling me every name under the sun because he didn't do it. You should have said, even if he did, it didn't matter. You knew it mattered at the time. But six months went by, and so it just inoculated it to the point to where everybody was talking about it didn't really matter then.

So I said, "Next time somebody is, for instance, oh, I don't know taking top secret emails and using them on their own server, instead of saying, yes, she did. No, she didn't. Yes, she did. No, she didn't. Does it matter that she did?" But nobody will ever go on record with it. So there's no way to win. But that's the lesson I learned. Does it matter if Benghazi did happen that way? And it wasn't about the film and she lied, does it matter? To me, yes, it does. I have found to those, they will argue and argue and argue. And in the end, it doesn't matter anyway. So is there any thing we can to do change it? How do we argue a different way?

STU: And that's a great point. Because I think if you get people to answer those questions, what you get the answer to that is no. It doesn't matter to them. Because essentially they're on a team.

GLENN: Yes.

STU: It's impossible to take --

GLENN: Take the offensive team.

STU: I can't argue to a Cowboys fan that they should no longer be a Cowboys fan. There's no logical argument that could ever overwhelm the idea that they like the Cowboys. Eagles is an even better example. I'm a huge Eagles fan. And despite the fact that they've won exactly zero Super Bowls --

GLENN: You're never coming off the Eagles.

STU: Right. I honestly don't care what you say. Their entire stadium is built with giant windmills at the top so they can focus on green energy. You hear me about global warming. I'm not a guy who likes those policies. But you'll never change my mind. That I'm an Eagles fan. So the answer that I believe to your question, essentially, is --

GLENN: Hopeless.

STU: There is not a phrase or approach that will --

GLENN: No, this is happy. This is good.

STU: No, this is really positive. But the answer is that people no longer make these decisions when it comes to elections based on the things we're talking about. Because I honestly believe with this audience and I think a lot of the people in this audience are on this side. But for the people that are holdouts in the Trump campaign. I honestly believed that if you could expose what this man said and believed, they would react to it. The reasoning is, they reacted to it with people like Mitt Romney, whose record is considerably more conservative than Donald Trump.

GLENN: Yes. Mitt Romney is more conservative --

STU: And I don't think he's a conservative guy at all.

GLENN: Yeah, I know.

STU: But he's way more conservative than Donald Trump. And when you go through the record, the same things that you look at and you say, okay. Well, Mitt Romney is a problem. I mean, we had 100,000 calls in the last campaign. Mitt Romney is a problem because he flip-flopped on these issues. I don't trust him on this.

Donald Trump is way, way worse. He's changing his mind week to week on major issues, and it just doesn't matter to that slice of the electorate. Like, if Donald Trump came out and said last week he donated to Barack Obama, would that matter? No.

PAT: I don't think it would. I don't think it would.

STU: It would not party. Once you're on that team, you're on that team. So I don't know how you can possibly change that. They're going to be fans of the squad they love. And that's the thing, period.

PAT: And here's the thing, if Ted Cruz started talking about income inequality today and the fact that women make less than men in the workforce and started using the false statistics that Democrats do, we'd jump off that bandwagon.

GLENN: I'd be off that team today. I'd be off that team.

PAT: We'd be off that bandwagon.

JEFFY: But Ted Cruz is trying that. Right? He's changed that up. Instead of preaching to Stu about how bad the Eagles are, you would just eventually tell them how good another team is and hope that he comes on board with that team and leaves the Eagles on his own. And that's Ted Cruz's plan, right? So instead of being negative --

GLENN: So maybe that's where we went wrong. Instead of saying -- and this is really kind of your first answer, Stu. Have a better candidate.

PAT: Have a better alternative.

GLENN: When I asked you, what did we wrong in 2008? Have a better candidate.

Well, okay. We can't control that. But --

STU: We can.

GLENN: Okay. Here's the thing. Yes, we can. But here's the thing. I spent my last eight years and you've spent your last eight years if you've listened to me and you understand what I'm saying, you've spent your last eight years and maybe, quite honestly, your last 15 years trying to be consistent in your life. Trying to say, "Okay. What does the world really mean? What is really happening to our country? What is happening overseas?" You don't accept things like, "Oh, well, this has nothing to do with Islam." You know it does, and you know that is inconsistent with reality.

So those little inconsistencies with reality bother you. So over the last eight years, especially, you have said, "Okay. What was one of the problems with George?" One of the problems with George Bush was, he got into office, and the Republicans did exactly what they said they weren't going to do. They spent as much money -- well, not as much money as this guy -- but they spent as much money as the last guy. They did the same policies. They had the same things. They were spying on us. They did all the things we said no to.

And so we realized when we got into 2008, one of the things that we have to be, to be able to have any credibility and to be able to win long-term is to be consistent, is to actually stand for something. And so we've spent the last eight years trying to stand for something. Trying to stand up and say, "No, no. I don't care if I win or lose. I wanted to mean something. I want -- I want my word to mean something. I want to be able to stand and sleep at night and say I wasn't part of the problem. I want to be able to go in 2020 and be able to argue, no, my president, what I said and what my candidate said he would do, he did. He didn't get into office and just do exactly the same damn thing that Barack Obama was doing.