From Jon Fleischman - So, Does It Matter? <[email protected]>
Subject Written Version Of This Morning’s Podcast on Prop. 50 - By Popular Request…
Date October 22, 2025 10:37 PM
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This morning I published a 25 minutes or so podcast on why Prop. 50 in California is likely to pass. I got into a lot of details. Now I’ve been inundated with requests from people wanting to read it rather than listen to it. I don’t know if I should be offended? Anyways, if AI did its job right below is a digestible but very lengthy copy of what I said in my podcast. It’s not quite a transcript. I had it formatted differently for ease of reading…
Here is a link [ [link removed] ] to the video podcast and also at this link you can find a YouTube video and also players for Apple podcasts Spotify, etc.
SO, DOES IT MATTER? PODCAST ON PROP. 50 — FORMATTED TO READ
Podcast Summary: Proposition 50 and California Politics
Introduction to Jon Fleischman and the Podcast:
“Hey, it’s Jon Fleischman, and welcome to a podcast for the So Does It Matter website on California politics. Or maybe it’s really supposed to be pronounced so. Does it matter? That’s really how we’re supposed to say it, because we’re talking about things that truly matter going on in California politics, largely in California politics. I stray every once in a while.”
“Anyways, by way of self-introduction, for those of you who might be tuning in for the first time, my name is John Fleischman. I’ve been involved in California politics for well over three decades. It seems like a long time ago, since the late 80s, when I first got involved.”
“Ronald Reagan was president of the United States, and I actually got to meet him. Shortly after his presidency, I got to have Taco Bell with him. For those who are curious, he loved the Enchirito. But that’s a whole other story for another day.”
“Anyways, I’ve been working on campaigns and involved with punditry and analyzing California politics for a very, very long time. I’ve built up a very large network of contacts and people. I have a lot of experience to draw upon.”
Call to Action for Engagement:
“But before we get into that, I just wanted to take an opportunity to ask you, if you’re already here on the So Does It Matter? Substack to make sure that you’re sharing this, that you’re restacking it. If you’re watching it on Substack, that you’re liking it. Those are the kinds of things that help me out with what I’m doing.”
Purpose and Context of the Episode:
“I’m actually filming this podcast from my car because that’s how busy this week has been. But I wanted to make sure that I brought something to you.”
“Normally, I do a one-on-one interview every week. and those are available if you go to the archive button you can find those especially if you need to search type in one pull up all the one-on-one interviews we’ve done a bunch of them this week my special guest had to postpone and i decided rather than trying to scramble and inconvenience somebody at the last minute I would give you some one-on-one entertainment with the one-on-one being me and you.”
“So today I want to talk about Proposition 50. And this is not a very pleasant conversation to be having when I’m talking to a conservative or a Republican. If you’re a liberal Democrat watching this, you might be more gleeful. because we’re going to have some truth talk about Proposition 50.”
Proposition 50 Overview and Current Status:
“The first thing I would say is we sit here, I’m looking, it’s the first of Tuesday. People have had their ballots for quite some time. The end of the election is just a couple of weeks away.”
“And I think it’s pretty obvious to anybody who’s not trying to be deceitful or mislead anybody that the yes side is ahead. I think that if the votes were stopped today and they were tallied, I wouldn’t be surprised to see the yes side winning by double digits.”
“Does that mean that it’s a fait accompli? Does that mean that it cannot change? No. But as the election progresses, it gets harder to change because, of course, a bunch of votes are in the bank and those votes are all being put in the bank when the lead is larger for the yes side. And so if the no side surges and comes back, they’ve got to make up a gap that was created by the first couple of weeks of voting.”
Reasons for Yes on 50’s Lead:
“So what are the reasons why the yes on 50 side is ahead? Well, I guess you can boil that down to two reasons, messaging and money, right?”
“So first and foremost, I think that in a blue state like California, The anti-Trump messaging is resonating. It’s doing very well.”
“You’ll notice there’s not a whole lot of pro-Newsom messaging. He’s not in the commercials. He’s not in the spots. There’s been an exclusive discipline on basically saying, if you want to offset what Donald Trump has done, if you want to send a message to Donald Trump, if you want to express a vote of no confidence in Donald Trump, Proposition 50 is the time and the place to do it.”
“So you’ve got all that messaging that’s out there, but then you have to add to it the enormous amount of money that’s been brought in by the Yes on 50 campaign.”
“I have written about, and I’ll put in the show notes, some of the nefarious ways that money is being raised. My favorite examples are all the millions of dollars coming in from the public employee unions who are doing their solid for Gavin Newsom, who has gone out of his way to be very generous with your tax money, helping them to get raises, helping them to get more benefits, helping them to get better job circumstances. And it’s pretty outrageous, but that’s just one example.”
“But what’s most significant here is that the Yes On campaign has been on television, on digital communication, in mailboxes from well before when ballots came out through now. And it’s relentless and it’s not stopping.”
“It’s not only the official Yes On campaign, but it’s also Tom Steyer’s put in a bunch of money. There’s different money coming from different places. And, you know, wherever you are, you’re seeing these ads.”
Republican Side Campaign Structure and Funding:
“And so to contrast that, we’ve got the Republican side. And when I say the Republican side, it’s kind of there was a split campaign, which was always awkward.”
“You had kind of a good government no on 50 effort that was being spearheaded or is being spearheaded. by charles munger jr that’s not a household phrase for many those in california politics probably know who he is his father charles munger senior was the business partner of warren buffett a billionaire well warren buffett was a billionaire and so was charles munger senior and so charles munger jr is one of the kids and so has benefited financially from having a very wealthy father and so he put in a bunch of money to pass The California Redistricting Commission in 2008, more money in 2010 to have the commission also handle congressional lines, not just as… the lines for the state legislature.”
“And now he has put in, I think, some $32 million to start the messaging campaign right away against Prop 50. But it was always envisioned that that was going to be a partnership, but it has not turned out to be really much of a partnership.”
“So there’s a partisan campaign against Proposition 50 on the Republican side, and that’s more or less been spearheaded by former House Speaker Kevin McCarthy, former California Republican Chair Jessica Patterson, They kind of teamed up and announced they would be spearheading the no side.”
“And then, of course, the California Republican Party with Chair Corin Rankin is been involved with their efforts, as well as all of the local efforts around California.”
“But that has not gone as well as one would like. Kevin McCarthy moved seven figures from a committee he controlled. There’s been some other notable contributions that have come in, but all some in total. I would say that the partisan effort on the Republican side against Prop 50s 10 million 15 million certainly south of 15 million i apologize i didn’t look up the numbers before recording this but the numbers are really low relatively to the democrat numbers”
“but maybe what’s more significant is that money’s been largely spent at least the majority of it’s been spent and uh while there was a a a later five million dollar contribution that that came over from the congressional leadership fund i believe so that’s the speaker’s money even though it’s not the speaker’s money”
“That money I haven’t really seen deployed other than I’m starting to see people get some mail. And as somebody who does political campaigns from time to time, I don’t even know what that would be about because the most cost effective way to communicate with California Republicans who are likely to vote or who need to vote is going to be digital first. and maybe some mail to older people that aren’t really using technology that much.”
“But I had a friend who just told me about how their 21-year-old son just got a piece of snail mail telling them why Prop 50 is bad. So somebody’s wasting money on the Republican side.”
Campaign Visibility Disparity:
“But so you basically got two ecosystems going on. If you’re a Democrat right now, there’s a big election going on. You’re seeing stuff on television. You’re seeing stuff on digital, whether you’re on YouTube or streaming Roku, wherever you are, you’re seeing it. If you’re on your phone, if you’re going on apps, you’re seeing static ads, Google ads, lots going on. If you’re on the on podcasting, you’re hearing ads. And then, of course, your mailbox is full. So if you’re a Democrat, it’s campaign season, you know to go out and vote.”
“If you’re a Republican, I was just talking to some Republicans who are like, other than getting a ballot in the mail, we’ve heard nothing from anyone to cause us to believe anybody cares how we vote. And that’s a resource issue. And the reality is Republicans have a horrible, horrible resource issue, and it makes it very, very difficult. And it makes things very, very one-sided.”
Challenges and Need for a Game Change:
“In a minute, I’m going to walk you through why I think there’s a Republican resource issue. But I will say that I think Republicans are kind of at fourth and 40 here. There needs to be some sort of game change, something that happens that changes the way things are going, something that causes a bunch of resources to be deployed, or the part of defeating Proposition 50 that takes place at the ballot is simply not going to happen.”
“You can have all the most earnest volunteers that you want, all the most earnest ground game activity that you want, but California is too big of a state.”
“Thank you. Because he hasn’t weighed in. Arguably, he hasn’t weighed in because he’s not popular in California. But Republicans are not voting. And maybe his weighing in would cause more Republicans to get out there and actually vote.”
“Frank Schubert, a longtime conservative consultant in California, friend of mine, is in the article quoted talking about it basically like, what have you got to lose at this point? Because what’s really not happening is money is not coming out to California to fight the measure. And maybe the president’s engagement would cause that.”
“So it’s a catch-22. Engage the president to try to create a catalyst, something to change the dynamic. But I’ll tell you, there’s going to be Gavin Newsom and a bunch of Democrats who are going to be like, that seals it. That’s our narrative. We were telling everybody this is anti-Trump, and here he is to tell you. That it’s anti-Trump. So that’s very dangerous. We’ll see what happens.”
Why Funding Disparity Exists - National Republican Priorities:
“But as I think about why it is that there’s this funding disparity and what’s going on, I kind of look at it this way. You’re the speaker. You’re the people around the speaker. You’re in Washington, D.C. And you’re trying to figure out what’s the play here because there’s one priority. And that one priority is not preserving House seats in California. It’s preserving the Republican majority in Washington, D.C. into the next Congress, which you would think would include lots of seats from California, but it doesn’t have to.”
“And so here’s what’s going on. They say to themselves, we could put in $50, $75 million, $100 million to make sure that we’re getting out the Republican vote. We can also, there’s creative ways to use that money to help make sure that independents and even moderate Democrats are being communicated with.”
“I actually think that if Republicans put in more money, Munger might then say, okay, I’ve got dance partners and he would put in more money for his effort.”
“But the calculus that goes on is, okay, $50, $75, $100 million in And it’s a crapshoot. We put in all of that money and maybe we win and we defeat the measure, but maybe we lose. If we lose, we’re out all that money and Prop 50 has passed and we’re down to what? Four safe Republican seats in California. Five incumbents are gone and the opportunity to go after… you know, three or four other seats are gone.”
“Okay. On the other hand, if you don’t put 50 to 75 to $100 million into that effort, you save that money because there’s a finite amount of money and you’re able to then take that money and deploy it in other states. where there are competitive districts around the country. I don’t have the numbers in front of me, but trust me, they’re there.”
“And now all of a sudden you get to compete. And a lot of those seats, that kind of money goes a very, very long way because, of course, many of our seats in California are in areas like outskirts of Los Angeles, Orange County, Inland Empire, that L.A. media market that’s extraordinarily expensive in which to compete.”
“And so they have to make that calculus and kind of decide because there is a very realistic way to look at this where you say the road to the White House already does not include California. The road to a U.S. Senate majority, well, they have a majority and there’s no Republican senators from California, nor are there likely to be anytime soon.”
“And right now, the road to a Republican majority in the Congress does include California because the We only have a Republican majority by a few seats, and we have nine members of Congress who are Republican from California. But it doesn’t have to include California.”
“As we know, there’s this big national redistricting, mid-decade redistricting going on. Texas may pick up four or five new Republican seats, which would offset the loss in California or California. The narrative is that it’s flipped around, but there’s also redistricting efforts going on in other states, Louisiana, Florida, possibly Ohio, possibly Indiana. The list goes on. Nationally, Republicans could benefit by double-digit jump in seats, even if they lose the seats in California.”
“So they’re sitting there going, where do we deploy our money? And then to add to it, if they manage to deploy 50, 75, 100 million dollars on Prop 50 in California and they’re victorious, which means Prop 50 is defeated, then they need to come up with another $30, $40, $50 million. They have to defend Young Kim. They have to defend Ken Calvert. They have to defend David Valadao, right? And then they got to come up with money if they want to try to take out Tran and Min in Orange County, Levin in San Diego. if they want to try to take out harder, gray, all those different options and seats cost a lot of money.”
“And frankly, there’s some simplification that takes place if all those are off the table and you’re using your money elsewhere. I’m not saying that’s a good plan, but it could be appealing from the point of view of trying to simplify what you need to do.”
“And then also there’s a lot of money that gets raised in California. There’s a lot of money that’s raised for national congressional efforts out of California. And I’m going to turn on the light. See how that does. That doesn’t really do much. And that money right now, a lot of that money gets tied down in California where it’s needed.”
“But there’s also something to be said that if there’s four safe Republican seats in California and you’re raising millions of dollars out of California for congressional races, that gets added. to other races outside of Southern California that are in play.”
“So I think that’s a lot of the equation that goes on and that’s consistent with what you’re seeing. Because while there is money coming out of DC, I just mentioned $5 million coming from the leadership fund and out of DC. That’s not really enough money to make a difference. But it would be enough money to say, hey, nine members from California where I need your votes because I need you all. I’m doing something.”
“So I think that may be what’s going on. That’s my take. That’s my analysis. That’s the way I see it. Somebody can prove me wrong.”
Advice to Republican Activists and D-Day Analogy:
“And so I would say this to Republicans that are watching this, especially activists, party leaders, party officers. County party leaders, activists that are trying to make a difference. You need to continue doing what you are doing because it can make the difference, but it’s only going to make a difference if, um, if in fact there’s national money flowing in and there’s a big, big so that people who are Republicans actually feel like they’re being contacted by every way possible because you can’t hit every door, not even close.”
“And so you’ve got to be able to be on digital mailboxes, radio, advertising and podcasts, all the different things that you would do. And right now, Republicans are not doing that. I would hazard to say that Republicans, in terms of an air war, are virtually silent. And that’s not going to pass a ballot measure.”
“I would make this analogy. I’ve made it with some people. But think back to D-Day and the invasion of Normandy Beach. Three things had to be going on in order for the invasion of Normandy to be successful.”
“The first thing was you needed a big ground force to invade Normandy Beach, right? And that would be the equivalent to the ground campaign going on. People need to be out there storming the beach, making a difference.”
“Of course, also what happened during the invasion of Normandy were dozens, if not more, big, huge battleships that were parked 20 miles off the coast of Normandy Beach and all the other beaches. And they were shelling the German gun emplacements with bombs, with missiles, larger than Volkswagen vans. shooting them over. This caused not only the gun emplacements to be destroyed, but the Germans were forced to pull back all their tanks and those kinds of heavy equipment or they’d get blown up by the thousands and thousands of shells that came down.”
“Well, in my analogy, all the mail, the digital, the phones, all of that stuff, those are the battleships shelling the emplacements. And that’s what’s missing right now.”
“Think about what would have happened in Normandy if the troops tried to invade the beach, but no one had taken out the German guns and the tanks and all of that. Just everyone on the beach would be destroyed.”
“So our Republican volunteers and activists need to keep working, but they’re not going to be successful if we don’t get those battleships back out there. And I’m hoping… that that happens. It needs to happen or the writing’s on the wall, people. The status quo is for a lost election.”
“And then for those who are curious, the third factor that needed to be present to have a victory at Normandy was the atmosphere, the weather. It needed to be overcast, in order to keep the planes from flying overhead. And in this case, the atmosphere works in the favor of the other party, right? A special election in an off year where you’re dealing with a motivated base, that doesn’t help us. And so it makes it even more important that the battleships show up And that we’re able to shell the emplacements.”
“So that’s kind of the way I see things now. I use the expression fourth and 40. That’s a football term. That means you’re on the fourth down and you got 40 yards to go. And you’re starting to think about whether or not you need a Hail Mary, whether that’s Donald Trump coming out. I don’t know. But this is what needs to happen in order for there to be a sea change. in what’s going on for Proposition 50 not to pass.”
Potential for Litigation if Prop 50 Passes:
“So I will say this before I close this commentary, and that’s that there is one more thing to go. The battle for Prop 50 is certainly right now at the ballot box. And if it’s defeated at the ballot box, great. The battle for Prop 50 is over. But that’s not the last theater of battle.”
“After Proposition 50 passes, if it passes, then we enter a new phase called lawfare, the litigation piece. And I’m not talking about litigation in state court. We’ve talked about this before. California Supreme Court is made up of six appointees who are from Democrat governors, three from Governor Newsom, three from Governor Brown, one from Arnold Schwarzenegger.”
“That Supreme Court is so in the tank that there were two separate lawsuits filed into the Supreme Court asking for them to hold an emergency hearing and stop Prop 50 from going ahead to the ballot. I wish I could tell you that the Supreme Court gathered and that both sides presented their cases and they adjudicated in chambers and came out. And it was a tough decision, a split court, but it didn’t go our way. That would at least have some sort of feeling like there was due process.”
“Actually, in both cases, the Supreme Court rejected on its face the emergency applications to hear a case, so they were never heard at all. State court was never going to be the case where it was heard, but you’ve got to check the boxes. You’ve got to make the case that no stone was left unturned.”
“Federal court is another matter. Federal court is, as you know, when you get to the very top of it at the Supreme Court, is a Republican court. It’s a six to three court with six Republican justices and three Democrat-appointed justices. And ultimately, any federal play probably ends up there.”
“I know that there’s been at least one federal lawsuit filed by Republican gubernatorial candidate Steve Hilton. I think there will be others that will be filed after the election.”
“There’s an obscure legal term called ripeness. Those lawyers can say, I know what that is. But for those of you who don’t, it has to kind of like a ripe piece of fruit, you know, when you bite into it, when it’s ready to be eaten. If not, it’s very sour. Well, in the political world, rightness is when is your case appropriately before the court?”
“And based on some of the stuff that’s come out of the Supreme Court, which is, of course, instructive to the whole judiciary, these cases are really not ripe until there’s something that’s, let’s see if I get this word right, justiciable, something that is properly before the court. And Prop 50 hasn’t been passed, so you can’t file action against the potential passage of Prop 50. You have to file passage against the passage of Prop 50.”
“And so I think once it’s passed, litigation will be filed. I think the litigation will be well financed. I think you will probably see litigation coming locally out of California. And you may also see litigation coming out of the United States Department of Justice.”
“I think the Department of Justice litigation may be more limited. Because like I said, there’s a national strategy. The Trump administration is not gonna file a lawsuit in a broad enough manner that their lawsuit could have the potential of overturning redistricting in a mid-decade in Texas or Ohio or Indiana or Florida or Louisiana, any of those states. They simply, that’s not something they would wanna do.”
“But there are some narrow circumstances in California that would allow them to sue on the grounds of things that are going on in California. However, the Hilton administration, the Hilton legislation, I think new legislation, latest legislation, litigation that will come out of California will, I think, contest things in a more broad sense.”
“What would be an example might be, hey, we haven’t redrawn lines since the census, which was now, what, six years old, five, six years old. How can you possibly guarantee one person, one vote without recounting? And so now they’re redrawing the lines and you don’t know where people live. And so are you depriving people of their opportunity to have equal representation in Congress? That’s just one argument.”
“So the point that I’m making in the dwindling light is that there’s an entire legal lawfare episode that is going to occur if Proposition 50 passes and I wouldn’t discount that. I do think that Democrats have a strong case. Going to the people for a vote is a very, very strong thing, I think, to have done. And I do think that if the people vote for this, that’s going to put a Republican lawfare effort behind the eight ball a little bit. But I wouldn’t rule it out. And I think that’s the next stage. if Prop 50 does pass at the ballot box.”
Call to Action and Closing:
“So that’s the way that I see it. We’re 25 minutes into this. If you like this kind of commentary, if you like me kind of going one-on-one to the camera, let me know. The best way to do that is to just hit reply to the email that you got this on and let me know. Or you could send an email to jon at sodositmatter.com, right? You can certainly post a comment below,”
“but I ask you to share this, restack it. If it’s an email, just forward the email to people. Although it’s a bit of a Debbie Downer, I wouldn’t forward it as a GOTV mechanism for getting people out to vote against Prop 50.”
“But I do think that we owe it to each other to be realistic and have a realistic understanding of the situation in which we find ourselves.”
“So before I hit the 26-minute mark, I’m going to end this by simply, again, asking you guys to share, support, and have a great day. I guess this is going to publish on Wednesday. Have a great Wednesday.”

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