Top Ten Winners & Losers In California Politics This Week - The Prop. 50 Edition

Each week we pick ten people or groups that had a particularly good or bad week, and label them winners or losers! For the week ending 11/7/25, it’s all about Prop. 50…

Below is our Top Ten List of Winners and Losers for the Week. This feature available to all of our subscribers, free and paid.

⏱️ 4 minute read

This is where we examine state and local politics (or national issues with a California angle), and highlight individuals (or groups) who have achieved notable successes or have had a particularly challenging week. This week, we are focusing exclusively on winners and losers as they relate to the successful Prop. 50 campaign. Readers know that I opposed this cynical effort to have politicians pick their voters instead of the other way around. However, readers also know that while I have my views, I strive to call balls and strikes fairly objectively, which made assembling this list a very challenging task, indeed!

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Also, the SDIM podcast this week (20 mins) is a verbal riff on this list (very entertaining):

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Top Ten Winners & Losers This Week in California Politics

⬆️ WINNER: GAVIN NEWSOM

Starting from his X post to President Trump on August 11, Newsom drove Prop. 50 from idea, to legislative achievement, to a massively bankrolled ballot measure, to a successful statewide vote (with a massive margin of victory). All in less than three months. His ability to dominate the process, particularly in securing substantial amounts of money from numerous unions and other entities that benefit financially from state government spending and policies, is both impressive and alarming. He has successfully further diminished California Republican voters, which I did not think was possible. He has pushed himself, for now, into pole position in these early states of the race for the Democratic nomination for President.

⬇️ LOSER: FORMER HOUSE SPEAKER KEVIN MCCARTHY

First rule of life - under promise and over deliver. When Newsom moved forward with his plans ,McCarthy was quick to proclaim in political circles that he would take ownership of raising $500 million for the partisan efforts to fight Prop. 50. So instead of being a winner for raising tens of millions of dollars, an impressive feat, he’s the loser who raised less than 10% of his goal. By the way, not easy to raise big bucks when GOP decision-makers inside the Beltway decide the risk/reward proposition didn’t make sense for them to go in with big bucks against the measure. For falling short of expectations he created, he gets this award.

⬇️ LOSER: ARNOLD SCHWARZENEGGER

The Governator is a political loser because of a lack of authentic, meaningful engagement in the effort to stop Prop. 50. The Former Governor could have helped raise campaign funds. He didn’t. He is vastly wealthy and could have put some of his own money in. He didn’t. He could have traveled the state, attending earned media events like those he held when he ran for office (remember the broom?). He didn’t. He made some public comments — but he never truly engaged. The non-action hero watched Gavin Newsom take a hatchet to part of his legacy.

⬆ SHAWN STEEL, REPUBLICAN NATIONAL COMMITTEEMAN

Even Generals in wars that are lost can show their quality, and their worth. Shawn took it upon himself to embark an uphill quest to raise money from DC to fight Prop. 50. Even though more direct and higher profile efforts failed to meet expectations (See McCarthy) Shawn was able to successfully raise around $11 million (which was unexpected). He also successfully lobbied the National Republican Congressional Committee to retain the Dhillon Law Group to litigate against Prop. 50. Solid work from my friend of … 37 years? Time flies.

⬆️ WINNER: PAUL MITCHELL, REDISTRICTING PARTNERS

When Prop. 50 in legislative form was being shoved quite inartfully through the legislative process, a partisan train running over anyone in its tracks. Firebrand GOP Assemblywoman Alexandra Macedo lit up the Democrats, who did not want to say that Democratic consultant Paul Mitchell drew the lines. I watched this with fascination while listening to Paul on a podcast for Capitol Weekly, happily talking about what it was like to draw the lines. As a conservativ,e I hate these lines so much that Paul has to be a winner. It occurs to me that someone also drew up the plans to the Death Star, as well. And convince Darth Vader that the plans were good.

⬇️ LOSER: CHARLES MUNGER, JR.

The scion of a wealthy family, Munger’s father was the billionaire business partner of Warren Buffett. Munger is not a loser like Schwarzenegger, who didn’t meaningfully engage. On the contrary, Munger, who spent heavily in 2008 and 2010 to fund the efforts first to create the independent redistricting measure and then to apply its worth to House districts, spent over $32 million of his not easily earned money to try and stop Prop. 50. He happily put that in, no doubt on the presumption (note the grand promises of McCarthy) that he would be met on the field of battle with big bucks from the GOP establishment. Oh, there were healthy funds raised, until you compared them to the over $170 million raised by the Yes on 50 efforts. Munger is a political loser for watching Newsom take a cleaver to his legacy. You are almost personally bad for Charles.

⬇️ LOSERS: CA GOP HOUSE MEMBERS LA MALFA, KILEY, VALADEO, CALVERT, KIM AND ISSA

Ahhh, the most challenging part of this column to write. Some of these individuals are close friends — all of whom I know and are dealing with being on the losing end of carefully drawn lines (see Winner Mitchell) that now make it likely that only one, maybe two of them, will be sworn in for another term in 2027. La Malfa will have to run against State Senate President Mike McGuire, who “lucked” into a brand-new safe Democratic seat, which is akin to storming Normandy Beach without air cover. Kiley’s district was ripped into a bunch of pieces. Unless he were to tilt at conservative hero Congressman Tom McClintock, in a new seat where McClintock has been representing 80% of the voters, he’s going to have to charge uphill hard. Valadeo has been barely getting reelected in what was a tough seat for a Republican, and now the seat just got a lot worse. Calvert and Kim were both drawn into the same ruby red district, but to use the only Highlander creed, “There can be only one.” Finally, Issa’s safe seat went from very red to definitely leaning/likely blue. There is some thought that he may jump into the mosh pit with Calvert and Kim. All in all, a crap-sandwich for these great Representatives who are victims of the new maps.

⬆️ WINNERS: DEMOCRAT CONSULTANT JIM DEBOO & HIS TEAM

Longtime Democratic operative and, for a time, Chief of Staff to Governor Newsom, DeBoo was the top person in charge of a vast organization tasked with implementing the vision that Newsom unveiled in early August. His winner status here isn’t really just for him, but for a bunch of lefty smart people who I don’t know but who really stepped it up in the moment. At the Academy Awards, these are the individuals who receive their Oscars at the ceremony where all technical achievements are recognized. Having personally overseen an organization that successfully passed twelve statewide ballot measures nationwide, I have tremendous respect for this achievement.

⬇️ LOSERS: COMMON CAUSE AND THE LEAGUE OF WOMEN VOTERS

These groups purport to support “good government” and were both strong supporters of creating the commission in the first place. Under the sheer political might of Newsom and his partisan organization, these groups just folded up their card tables and went home. Words that come to mind to describe these groups are principled, courageous, and committed. For those who enjoyed the movie Braveheart, these groups were essentially portrayed as Robert the Bruce, betraying their principles and revealing themselves to be cowards.

⬆️WINNERS: THE TEAM OVER AT POLITICO

There was some great coverage of the entire Prop. 50 campaign from a lot of publications, but frankly, the team at Politico took their reporting on this massive thing to another level, in both the quality, depth, and quantity of their efforts. I suppose the praise begins with the organization itself, for placing so many assets on covering this California political earthquake. The reporting was thorough, accurate, deep, and I will add creative. They covered angles on this that no one else did (like this one). I would name all the reporters, editors, graphics people, and fact checkers if I could. Too many to list. But great job to all of you, truly.

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This Top Ten List is also the Subject of Jon’s Weekly Podcast, where he gets even more unplugged. Check it out here.

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Now that you see what this column is all about, keep your eyes peeled. If you have someone you'd like to suggest for featuring in this column next week, please drop me a note. I will keep the names of those who make suggestions confidential.

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