Edgy Interview: Jon Fleischman

While my wife and I were lounging around vacationing in Hawaii, up popped Jon Flieschman on a news show. A debate ensued between a liberal commentator and Jon and my wife was impressed with Jon’s take on things. I said, “I know that guy.” She said, “Why don’t you do an Edgy Interview with him?” So…

Jon Fleischman has been a fixture in California politics long enough to know where the bodies are buried, but what stands out most about him is not his longevity — it’s his range. A conservative commentator, former executive director of the California Republican Party, founder of FlashReport, and now publisher of So, Does It Matter?, Jon has spent years helping shape and interpret the state’s political conversation. He brings conviction without affectation, deep institutional memory, and the kind of insider credibility that can’t be manufactured. But – as Edgy Interviewer readers know — the public persona is only part of the story. Jon’s also a cancer survivor, a lover of brass-driven music and classic fantasy, a serious steak enthusiast, and someone who fulfilled a childhood dream by serving as a reserve deputy sheriff. The result is a thoughtful battle-tested and grounded man with strong views and a perspective sharpened as much by gratitude as by politics. I think you’ll like learning about Jon in this interview.

When you were a child, what did you want to be when you grew up?

When I was growing up, I wanted to be a police officer. The thought of wearing a uniform and going after bad guys was very appealing to me. My career path didn’t take me that way. But in a way, I did live my dream – at the age of 37, I went through the Orange County Sheriff’s Academy (full stress, I might add!) and became a uniformed Reserve Deputy Sheriff. I spent over a decade giving back to my community. It was very meaningful to me. And allowed me to fulfill a childhood dream.

What was your favorite musical genre as a teenager and what are you listening to now?

As a teenager, the music that grabbed me most was the kind built around strong brass sections and big, energetic arrangements. I’ve always loved the sound of horns driving a song forward, so a lot of what I listened to fell into the world of pop, rock, and soul from the 1960s, 1970s, and into the 1980s. Bands like Chicago, Blood, Sweat & Tears, Tower of Power, and Earth, Wind & Fire really stood out because their music blended rock, soul, and funk with powerful brass instrumentation. Motown and soul artists also had a huge impact—acts like The Temptations, Marvin Gaye, and Stevie Wonder created songs that were both musically rich and timeless.

What’s interesting is a lot of that music has had incredible staying power. Those artists are still widely played today, and their sound continues to influence modern musicians. Lately I’ve also been listening to a lot of jazz, especially great modern trumpeters like Wynton Marsalis and Terence Blanchard, who carry forward the tradition of brass-driven music in a different style. And while the music world has changed, artists like Bruno Mars still draw heavily on the funk and soul sound that defined the era I grew up listening to.

I was reminded of that recently when I went to see Leonid & Friends, one of the top Chicago and Earth, Wind & Fire tribute bands. Ironically, the group is made up primarily of Russian and Ukrainian musicians who play together brilliantly—apparently either unaware they’re supposed to be at war or simply choosing to ignore it. Either way, the music was terrific.

What book — fiction or non-fiction — influenced you most?

The Lord of the Rings is the book trilogy that has influenced me the most. It has inspired me because of its timeless story about the struggle between good and evil and the courage required to stand against overwhelming odds. At its core, the story is about ordinary individuals who choose to do the right thing even when the cost is high and the chances of success are uncertain. The characters come from very different backgrounds and often have little in common at the start, yet they unite around a shared purpose: stopping a great evil that threatens the freedom of everyone in Middle-Earth.

What makes the story especially powerful is the willingness of its heroes to sacrifice for something larger than themselves. Frodo carries a burden that could easily destroy him. Sam remains loyal when it would be easier to walk away. Aragorn accepts the responsibility of leadership, while others risk their lives simply because they know it is the right thing to do.

For me, there is also an allegory about the dangers of concentrated power. The One Ring represents the corrupting force of power that can dominate and control others. The story suggests freedom is fragile and must be defended by those willing to resist tyranny. That message about preserving liberty against powerful forces resonates strongly with me. This motivates me in my political endeavors as a conservative.

If you could repeal one law, which would it be and why?

This one is easy. I would repeal the various laws that allow public employees to unionize. Much of the dire straits California finds itself in now, with high taxation and chronic overspending, is due to the extremely corrosive effect these unions have on public policy. They spend huge amounts of money to buy politicians (like Governors, state legislators, County Supervisors, City Councilmembers, School Board Trustees) – the ones who can then vote to increase public employee wages and benefits and pass pro-union policies. These compensation increases result in even more dues coming into the unions so they can buy more politicians. Rinse. Wash. Repeat… a doom loop for prudent fiscal stewardship of taxpayer funds.

Even President Franklin D. Roosevelt, a Democrat, warned nearly a century ago that collective bargaining could not be transplanted into government service because public officials cannot fully represent taxpayers when negotiating with organized employees.

You’re bluntly critical of tax increases and of those who support them. What’s the crux of your opposition?

My opposition to pretty much all tax increases is two-fold.

First: it is almost always the case that a proposed tax increase is a) really about providing government with more funds with which to increase pay and benefits for public workers (which are now generally significantly higher than in the private sector, especially when you consider generous defined benefit pension benefits), or b) to deal with shortfalls as a result of already having given out these raises. I find politicians find it easier to ask voters to increase taxes than to do the tough work of zero-based budgeting and “right-sizing” to ensure budgets are balanced.

The second is broader and concerns how much of a family’s income should be spent on government at every level. I basically lump the whole tax burden into one big bucket (federal, state, and local taxes) – and ask myself whether it is too high. When the answer is “yes,” I just oppose any increases on any front, as in the end, it all adds to this big lump sum of how much of my year I am working just to pay the government.

Tell us about starting the FlashReport back in the day.

I started the FlashReport in 2001, but the idea really began during the 2000 election cycle when I was serving as Executive Director of the California Republican Party. Every morning I would get up early and scour the internet for political news—anything related to California politics or national issues that might matter to our party leadership. I began forwarding interesting articles to the party chairman and members of the state party board, and over time those emails evolved into a daily news digest.

After leaving the party to take a nonpartisan role with the Orange County Sheriff’s Department, I missed being connected to the political world. During a lunch in San Clemente with my friend and mentor Ken Khachigian, I mentioned that. Ken suggested I expand the news emails I had been sending to him and others. That simple suggestion became the FlashReport.

In 2006, the FlashReport “flipped” from an email digest into a full website, where it had a great run covering California politics for many years. I finally wrapped it up at the end of last year as my focus shifted to my new project, www.SoDoesItMatter.com, which continues my work covering California politics.

How do you decide which stuff in CA politics is actually worth paying attention to and writing about?

I spend a lot of time every day looking at a lot of sources on politics and policy. My criteria for whether to write about something look like this: Is this something that matters? Is this a topic of high interest to my readers? And finally, do I have, or with some calls, can I get details so I can provide insight and analysis that otherwise isn’t out there? I also have an ideological agenda to push constitutional conservatism, which is an overlay on much of what I write. But I pride myself on calling balls and strikes, which usually manages at some point or another to annoy everyone across the whole political spectrum [Ed. I can relate].

If you were a competitive eater, which food would be your specialty?

If I were a competitive eater, my specialty would definitely be steak. I’ve always loved a good steak—really any cut, whether it’s a ribeye, filet, New York strip, or a rib eye marbled with fat. There’s something about a perfectly cooked steak that’s hard to beat. Grill it, smoke it, sear it—however it’s prepared, I’m all in.

I’ve seen the competition at Coney Island where they see who can eat all of the hot dogs. No thanks. I went to a hot dog factory once. Um, so gross.

What’s been your favorite sports moment?

My favorite sports moment was Freddie Freeman’s grand slam in Game 5 of the 2024 World Series—and the best part (and a big reason why it is my favorite moment) is I was there in the stadium when it happened. Postseason baseball always has incredible tension, but that moment felt different. When Freeman came to the plate with the bases loaded, everyone in the ballpark knew the game could turn on a single swing.

When he connected and the ball sailed out of the park, the place absolutely exploded. The noise, the excitement, fans jumping and hugging strangers—it was one of those unforgettable moments that remind you why live sports are so special. Watching a World Series grand slam in person was incredible, and it became even more surreal a few weeks ago when I got to meet Freddie at the Newport Beach Mayor’s Dinner. Seeing him in person after witnessing that moment live was amazing.

What part of your life would surprise people like me who only know your punditry and political work?

In 1998, I was diagnosed with stage 2c testicular cancer – it was advanced. I had to have two surgeries and very unpleasant chemotherapy treatments. Fortunately, I came out of it okay and was still able to have a wonderful family.

Two things happened because of this near-death experience. The first, which perhaps is the direct answer to your question, is I have become an evangelist for young men in their late 20’s and 30’s doing self-testing, because, caught early, TC is the most curable form of cancer. I will also say the experience was transformative for me in another, unexpected way. During that difficult time for me, many people reached out to me with support, including many of them political adversaries. Through this process, I learned decency and compassion do not neatly sort along ideological lines. Some of my best friends today are people I would never vote for, but I love them, nevertheless.