🚌 Buses, Budgets, and BS: Brothers DeSimone's Conservative Circus Rolls Into Town | WAKE UP 5.19.25
A ringside seat to how right-wing media manufactures fear about public transit while championing tax cuts that hurt the communities they claim to serve
This is based on Wake Up Live with Chris DeSimone, a MAGA-conservative podcast hosted by a mayoral candidate for Oro Valley, podcasting from Marana, perpetually hating on Tucson, brought to you by Live The Dream Media on 5/19/25.
😽 Keepin’ It Simple Summary for Younger Readers
👧🏾✊🏾👦🏾
Some people who talk on podcasts in Tucson 🎙️ like to make it sound like everything in the city is dangerous 😱 and broken 💥, especially things like buses 🚌 and schools 🏫 that many people use. They talk about how taxes are bad 💸, even when those taxes pay for important things like places for people to live who don't have enough money 🏠.
They also make fun of students 📚 who are having trouble with reading 📖 instead of thinking about how to help them 🤝. It's important to listen carefully to what people say about our community 👥 and think about whether they're telling the whole story 📖 or just the parts that make you scared 😨.
🗝️ Takeaways
🔊 Conservative podcast "Wake Up Live" uses fear-based narratives about crime and public transit to undermine support for progressive Mayor Romero and public services
💰 Dr. Joann DeFilippo's analysis of Pima County's budget deliberately mischaracterizes affordable housing investments as wasteful spending
📊 The podcast weaponizes education statistics (claiming 69% of TUSD graduates aren't proficient in reading) without discussing systemic underfunding or socioeconomic factors
🏛️ "Brother Joe" promotes economically dubious claims about tariffs and productivity while revealing hypocrisy in conservative positions on Social Security and Medicare
👨⚖️ The hosts call for publicly identifying and shaming judges who set "lenient" bail amounts, promoting a punishment-oriented approach to justice
🙏 Even religious discussions about Pope Leo XIV are filtered through a conservative political lens that prioritizes tradition over social justice concerns
Behind the Mic: Unpacking the Conservative Echo Chamber of "Wake Up Live"
The struggle for justice continues in the streets and on the airwaves...
In the scorching political landscape of Southern Arizona, where mirages aren't just optical illusions in the desert but political narratives crafted to distort reality, I found myself subjected to yesterday's episode of Chris DeSimone's podcast "Wake Up Live." For those unfamiliar with DeSimone's particular brand of conservative commentary, imagine Fox News but with cactus-sharp takes on Tucson's progressive leadership and a devotion to "small government" that mysteriously disappears when it comes to militarizing the border or expanding police budgets.
If DeSimone's podcast were a Sonoran Desert plant, it would definitely be a jumping cholla – painful to encounter and incredibly difficult to remove once it attaches to you.
The Conservative Cast: DeSimone, Dr. DeFilippo, and "Brother Joe"
Monday's lineup showcased DeSimone's usual "Triple D" ensemble – himself, Dr. Joann DeFilippo, and his ex-seminarian brother known as "Brother Joe" who, surprisingly, knows more than the Pope. Each took turns promoting a perspective that views taxes as inherently bad, publicly funded services as failures, and suggests that community issues should be addressed with reduced government and an infusion of "free market" solutions. However, when it comes to Trump’s Tariffs, the narrative shifts to endorse more government involvement and the contradiction of free markets becoming acceptable.
The show began with DeSimone proudly recounting how County Attorney Laura Conover had called him out at a police awards dinner for filming during a portion of the event she'd requested not be recorded. Rather than reflecting on basic etiquette or journalistic ethics, DeSimone positioned himself as a valiant truth-seeker, telling listeners: "Living in that girl's head rent-free," while chuckling about the interaction.
Yes, because referring to an elected county attorney as "that girl" is totally respectful and professional journalism. Someone get this man a Pulitzer.
Part I: Manufacturing Fear About Public Safety
The podcast quickly pivoted to showcasing reporter Chorus Nylander's pieces on public transportation safety in Tucson. The framing was masterfully manipulative – cherry-picking isolated incidents of crime at bus stops to paint a picture of a transit system in "crisis," with Mayor Regina Romero cast as the villain for suggesting that riding the bus remains, statistically speaking, quite safe.
"She is Nero. She is Nira. Fidlin, while the place is burning down," DeSimone declared dramatically, comparing Tucson's mayor to the Roman emperor who allegedly played music while Rome burned.
Joshua Jacobson with the "Tucson Crime Free Coalition" (a name that sounds suspiciously like it was focus-grouped to maximize fear) was featured prominently, stating: "Machete attacks, hatchet attacks... We've got even rapes that have occurred at the bus stop right now. It is reckless and irresponsible for any elected official to say that the bus stops and the buses are safe right now."
What's conveniently missing from this apocalyptic portrayal? Context. Data. Perspective. The fact that public transportation serves predominantly lower-income communities, who rely on it daily without incident. The reality that isolated crimes, while serious and requiring response, don't represent the typical transit experience for thousands of daily riders.
When conservatives say they want "tough on crime" policies, what they really mean is they want policies tough on poor people, people of color, and anyone else who relies on public services. Notice how we never hear calls to get "tough" on wage theft, corporate fraud, or environmental crimes that affect far more victims.
This segment closed with DeSimone complaining that judges aren't being tough enough on bail: "One of the things that Corey is missing is who are the judges? What is their names? Who are these people? They're just these nameless folks that no one knows. Let's do it. Call them out. Who's the ones that are too lenient on bail?"
The implications are clear – public safety requires judges who lock more people up, for longer, with higher bail amounts that poor defendants can't possibly afford. The progressive perspective that cash bail disproportionately punishes poverty rather than crime never enters the conversation.
Part II: Dr. DeFilippo's War on Community Investment
Dr. Joann DeFilippo's segment was a masterclass in conservative framing around taxes and public spending. Focusing on Pima County budget discussions and proposed property tax changes to fund affordable housing, DeFilippo deftly manipulated numbers and context to paint even modest investments in community needs as government overreach.
When discussing Supervisor Matt Heinz's proposal for affordable housing funding, DeFilippo demonstrated the fundamental contradiction at the heart of conservative economic thinking:
"They're talking about the fact of we're going to increase, increase, increase, increase, right. But everything that they're talking about on the proposed federal fiscal year 2026 budget and economic decision guide for Pima County is based on inflation, housing, consumer confidence, and federal funds rate, which are all considered unfavorable. And based on the fact that these are all unfavorable, that's why we're going to increase your primary property tax rate."
She continued: "If the economic outlook is unfavorable, you better not increase the primary property tax rate. Well, if anything, you should look at decreasing it so you can help the community out."
Yes, because nothing helps communities more during housing crises than defunding affordable housing initiatives. Brilliant logic there, Doctor.
What DeFilippo deliberately obscures is how investments in affordable housing actually help working families weather economic challenges. She presents a false choice between tax cuts and community wellbeing when decades of evidence show that targeted public investments in housing, healthcare, and education deliver far more benefit to working people than trickle-down tax cuts ever have.
DeSimone contributed this nuanced economic analysis: "There's a truckload of the working poor in Pima County that own a house. That's just it. I mean, come on."
Come on indeed, Chris. Many homeowners are precisely the "working poor" who are one major expense away from financial disaster – the very people who benefit from public services and community investments funded by property taxes.
Perhaps most telling was DeFilippo's disdain for the Pima Council on Aging supporting the affordable housing initiative: "Who do you think it's hit some of the worst implications of an increase in primary property tax? I really want to ask the Pima Council on Aging. Did you pull your seniors? Or is that your administration speaking?"
The implication that senior advocacy organizations don't understand seniors' needs better than conservative commentators is both arrogant and revealing of the right's tendency to speak for vulnerable populations rather than listening to their self-identified representatives.
Part III: "Brother Joe's" Economic Fantasy Land
The final segment featured "Brother Joe" discussing the Preakness horse race (complete with analogies about investments) before pivoting to economic commentary promoting Trump's tariff agenda while dismissing legitimate concerns about national debt and inflation.
"The only realistic way that this country is going to get out of that kind of debt is productivity," Brother Joe claimed. "Tariffs are not bad. You know, it does bring down the national debt."
This is economic fiction. Tariffs function as regressive taxes paid primarily by domestic consumers and manufacturers. They raise prices, reduce purchasing power, trigger retaliatory measures from trading partners, and historically have damaged economic growth – the very "productivity" Brother Joe claims to prize.
Their discussion of Congress and spending revealed the hollow core of conservative fiscal posturing:
DeSimone: "So in the end, right, we know that the Social Security, Medicare, Obamacare interest on debt is 75% of the budget. Right. No one's cutting any of that in Congress."
Brother Joe: "Because that's now the third rail... You force myself and my employer by gunpoint to put into Social Security. You're not even giving me interest on the money... I want my social security. Don't mess with it."
So they want smaller government and less spending, except on all the major spending categories that benefit themselves personally. Got it.
The solution to healthcare costs? Brother Joe offers this gem: "It's cheaper to give them a tax credit or tax benefit to take this liability off our balance sheet."
Yes, because privatizing healthcare has worked so well for controlling costs in America. We only pay twice what comparable countries do for the same outcomes. Clearly we need MORE market-based approaches!
The Education Crisis: Weaponizing Literacy Rates
Perhaps most disturbing was DeSimone's teaser about education, where he shared literacy rates for TUSD graduates: "69% of TUSD grads are not proficient in reading." While education outcomes deserve serious attention, the framing was clearly designed to undermine public education rather than support its improvement.
Brother Joe's response was particularly revealing: "Where do these children go, Christopher?" with DeSimone responding, "QuikTrip or jail."
This shocking exchange exposes the dehumanizing view these commentators have toward students in predominantly low-income and minority school districts. Rather than discussing the systemic underfunding of public education, the socioeconomic factors affecting student outcomes, or the deliberate policy choices that have created educational inequality, they jump straight to suggesting these young people are destined for criminality or low-wage service work.
The conservative playbook: Defund public education, complain about poor outcomes, use those outcomes to justify further defunding. Rinse and repeat until public schools collapse and private alternatives can sweep in to "save the day" – for those who can afford them.
The Bigger Picture: Why This Matters to YOU
Podcasts like "Wake Up Live" aren't merely entertainment for conservative listeners – they actively shape the political landscape we all inhabit. When DeSimone announces that Pima County will pull "$43 million out of the private sector's hands for their crappy government," he's not just expressing an opinion – he's framing taxation as theft rather than the legitimate funding mechanism for services we all rely on.
When Dr. DeFilippo attacks affordable housing initiatives while claiming to care about working people, she contributes to a political environment in which addressing the housing crisis becomes harder.
When Brother Joe dismisses economic expertise in favor of simplistic tariff boosterism, he helps normalize policies that would harm the very listeners who tune in for financial guidance.
For Tucson's working families, immigrants, students, seniors, and everyone who relies on public services and community investments, these narratives directly threaten their wellbeing by undermining support for policies that would help them.
Every time you hear someone complain about "high taxes" in Arizona – which has some of the lowest tax rates in the country – remember that they're really complaining about investing in YOUR schools, YOUR roads, YOUR parks, and YOUR community services.
Religious Right-Wing Messaging
The podcast wrapped up with a discussion of Pope Leo XIV, focusing on the Latin Mass and religious politics, which revealed their alignment with the most conservative elements of Catholicism. The fixation on traditional Latin Mass over community engagement and social justice issues highlights how even religious discussion serves their conservative narrative.
"Catholics, Christians, they're persecuted to go to church," Brother Joe claimed, before pivoting to criticize the previous Pope's approach to China. The selective concern for religious freedom – passionate when it involves conservative Catholics, absent when discussing Muslims, indigenous spiritual practitioners, or progressive faith communities – exposes the partisan lens through which they view even religious issues.
A Call to Action: Reclaiming Our Narrative
For progressive Tucsonans, understanding these narratives is crucial for developing effective counter-messaging that addresses real concerns while offering vision and hope rather than fear and division.
We can acknowledge that public safety matters without demonizing those who rely on public transportation.
We can recognize legitimate concerns about government efficiency without abandoning the crucial role public investment plays in creating a just and equitable community.
We can demand excellent education for all children without using test scores as weapons against public schools and teachers.
The path forward isn't ignoring these voices but understanding them, responding with fact-based alternatives, and continuing to organize for the community we know is possible – one with affordable housing, safe public transit, well-funded schools, and an economy that works for everyone, not just those at the top.
The Three Sonorans will continue monitoring local conservative media to bring you these analyses and perspectives you won't find elsewhere. Your support through our Substack subscription helps us keep this critical work going – consider becoming a paid subscriber today to ensure we can continue bringing light to the shadows where regressive policies and narratives breed.
Questions to Consider
How have you experienced the disconnect between conservative narratives about public services and the reality of those services in your own life?
What strategies have you found effective for discussing issues like taxation, public safety, or education with friends or family who consume media like "Wake Up Live"?
How can we center the voices of those most affected by policy decisions – transit riders, public school families, affordable housing advocates – in our local media landscape?
What vision of Tucson would you like to see advocated for that addresses real community needs while inspiring hope rather than fear?
Share your thoughts in the comments below – your perspectives and experiences are a vital part of building the progressive community we need to counter these harmful narratives.
This blog is part of Three Sonorans' ongoing local media and politics coverage. Follow us for more analysis that centers the experiences of Native American, Chicano, African-American, and Asian-American communities in Southern Arizona. Support our work by subscribing to our Substack and sharing this content with others who are committed to a more just and equitable Tucson.
Quotes:
"She is Nero. She is Nira. Fidlin, while the place is burning down." - Chris DeSimone attacking Mayor Regina Romero regarding public transit safety
"Machete attacks, hatchet attacks... We've got even rapes that have occurred at the bus stop right now. It is reckless and is irresponsible for any elected official to say that the bus stops and the buses are safe right now." - Joshua Jacobson, Tucson Crime Free Coalition, using isolated incidents to characterize the entire transit system
"If the economic outlook is unfavorable, you better not increase the primary property tax rate. Well, if anything, you should look at decreasing it so you can help the community out." - Dr. Joann DeFilippo, misrepresenting how tax cuts affect community services during economic downturns
"Where do these children go, Christopher?" "QuikTrip or jail." - Exchange between Brother Joe and Chris DeSimone about TUSD graduates with low reading proficiency, demonstrating dehumanizing attitudes toward public school students
"The only realistic way that this country is going to get out of that kind of debt is productivity. Tariffs are not bad. You know, it does bring down the national debt." - Brother Joe, making economically questionable claims about tariffs and productivity
"There's a truckload of the working poor in Pima County that own a house. That's just it. I mean, come on." - Chris DeSimone, using working poor homeowners as a reason to oppose property taxes that fund services these same populations often need
People Mentioned with Notable Quotes
Chris DeSimone - Host of Wake Up Live podcast
"Living in that girl's head rent-free" (referring to County Attorney Laura Conover)
"69% of TUSD grads are not proficient in reading"
Dr. Joann DeFilippo - Regular guest/commentator
"They're complaining about the loss of taxpayer dollars, yet they're willing to spend thousands of dollars in these frivolous, I'm going to call it a frivolous lawsuit."
"Who do you think it's hit some of the worst implications of an increase in primary property tax? I really want to ask the Pima Council on Aging. Did you pull your seniors?"
"Brother Joe" - Regular guest/commentator focused on economics and investments
"You force myself and my employer by gunpoint to put into Social Security. You're not even giving me interest on the money... I want my social security. Don't mess with it."
"Catholics, Christians, they're persecuted to go to church"
Laura Conover - Pima County Attorney, mentioned as having called out DeSimone at a police awards dinner
According to DeSimone: "Chris, can you shut your phone off for this part"
Regina Romero - Mayor of Tucson, criticized for statements about transit safety
No direct quotes from her in the transcript
Joshua Jacobson - Tucson Crime Free Coalition
"It is reckless and is irresponsible for any elected official to say that the bus stops and the buses are safe right now"
Chorus Nylander - Reporter whose pieces on bus safety and judicial decisions were featured
No direct quotes from Nylander himself, only his reporting
Matt Heinz - County Supervisor proposing affordable housing funding
No direct quotes, but discussed regarding his affordable housing proposals
Pope Leo XIV - Newly appointed Pope, discussed in religious segment
No direct quotes, only commentary about his policies
Jan Lesher - County Administrator whose memos were discussed by Dr. DeFilippo
No direct quotes, but Dr. DeFilippo referenced her budget memos
Have a scoop or a story you want us to follow up on? Send us a message!
