Nov. 4, 2025

MM#444--From Tammany Hall To Today: The Long Shadow Over New York’s Mayor’s Race

FAN MAIL--We would love YOUR feedback--Send us a Text Message New York stands at a crossroads where history hums beneath every headline. We open the archive on the city’s most contentious mayors—Boss Tweed’s machine, Fernando Wood’s secession gambit, Oakey Hall’s complicity, and Jimmy Walker’s glamour-soaked graft—to understand how power, patronage, and public appetite shaped what’s possible in City Hall. That backdrop sharpens the stakes of today’s race, where frontrunner Zoran Mandani pitch...

FAN MAIL--We would love YOUR feedback--Send us a Text Message

New York stands at a crossroads where history hums beneath every headline. We open the archive on the city’s most contentious mayors—Boss Tweed’s machine, Fernando Wood’s secession gambit, Oakey Hall’s complicity, and Jimmy Walker’s glamour-soaked graft—to understand how power, patronage, and public appetite shaped what’s possible in City Hall. That backdrop sharpens the stakes of today’s race, where frontrunner Zoran Mandani pitches “pragmatic socialism” with a $30 minimum wage by 2030, rent freezes, fare-free buses, and new taxes on the city’s wealthiest.

We examine how ambitious social policy collides with budget constraints, competitiveness, and quality of services. What does it take to fund fare-free transit without starving maintenance? How do rent controls affect housing supply, vacancies, and enforcement? Can a city expand safety by pairing officers with social workers while stabilizing recruitment and morale? Along the way, we probe Mandani’s foreign policy posture around the ICC and diplomatic immunity, highlighting the legal limits of municipal authority and the risk of symbolic fights that distract from core city functions.

Zooming out, we scan pivotal races in New Jersey and Virginia to gauge how suburban and urban voters are sorting themselves on taxes, schools, and criminal justice. New York remains a bellwether: when it moves, policy markets listen. We bring receipts, historical parallels, and hard questions to test whether bold promises can become durable progress rather than another spin of the patronage wheel. If you care about the future of urban governance, budgets, public safety, and the health of democratic institutions, this one’s essential listening.

If the conversation resonates, follow the show, share it with a friend, and leave a review with your predictions for these races—what outcome do you expect, and why?

Key Points from the Episode:

• setting the stakes for the New York City mayoral race
• Boss Tweed and Tammany Hall as foundations of machine politics
• Fernando Wood’s secession plan and public backlash
• Oakey Hall and Jimmy Walker as later cycles of graft
• modern allegations and the need for civic guardrails
• Mandani’s platform on wages, rents, transit, and taxes
• policing shifts, recruitment strain, and social worker pairing
• diplomatic and legal limits on municipal foreign policy stances
• first 100 days scenarios and funding realities
• New Jersey and Virginia races as regional bellwethers
• predictions, risks, and what to watch next

Other resources:

Want to leave a review? Click here, and if we earned a five-star review from you **high five and knuckle bumps**, we appreciate it greatly!

00:00 - Setting The Stakes In NYC

00:31 - Today’s Mayoral Race Overview

01:43 - Boss Tweed And Tammany Power

03:09 - Fernando Wood’s Secession Gambit

07:38 - Public Backlash And War Pivot

10:43 - Draft Riots Foreshadowing

11:01 - Oakey Hall And Jimmy Walker

12:05 - Eric Adams Indictment Context

12:37 - Zoran Mandani’s Platform And Risks

15:04 - Foreign Policy And ICC Stance

16:43 - Policing, Endorsements, And Leftward Pull

18:19 - First 100 Days Scenarios

19:45 - National Bellwether Questions

20:43 - Key Races In NJ And VA

22:23 - Closing Views And Next Steps

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Welcome to the Theory to Action Podcast, where we examine the timeless treasures of wisdom from the great books in less time to help you take action immediately and ultimately to create and lead a flourishing life.

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Now, here's your host, David Kaiser.

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Hello, I'm David, and welcome back to another Mojo Minute.

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Grab some coffee today.

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We're not going to be covering a book, but we're going to be covering the news of the day.

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Today, voters in New York City will be going for the mayor's race.

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So we're going to be examining the New York City's mayor race.

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And we're also going to be going back and examining New York City's history of corrupt mayors from the 19th century to the president.

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We're going to connect it to today's high-stakes mayoral election.

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And the frontrunner, as you know, if you have not been living under a rock, is Zoran Mandani, a 34-year-old Marxist socialist and former state assemblyman.

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Now, if elected, Mondani would become New York City's first openly Marxist and socialist mayor.

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His platform and potential victory raises serious, serious questions about the direction not just of that city, but of American urban governance.

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But let's go back to the historical record of New York City because it has had some issues.

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Going all the way back to William Boss Tweed, who served as mayor from 1858 to 1861, his real power came from leading Tammany Hall, that great 19th century Democratic machine.

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Great, meaning not great in as in good, but great as in overwhelming.

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Been around for over a hundred years, completely just took over democratic politics in New York City for over a century.

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Now, Bosch Tweed, his ring embezzled what could be called over$200 million in today's money with inflated contracts and kickbacks, fake invoices, and all the such.

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The New York City County Courthouse originally budgeted$250,000 for his time, but he rang in a budget of$13 million with the overage siphoned off.

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Now he was exposed by the then New York Times and the Thomas Nass Political Cartoons.

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Ultimately led to his 1873 conviction on fraud and larceny charges.

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That dude bolted to Spain.

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He was extradited and he eventually died in prison.

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Now our second most corrupt mayor of New York City was a guy named Fernando Wood.

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He was the mayor in the 1850s and early 1860s.

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Again, he was a Tammany Hall operative who perfected patronage and voter intimidation.

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He actually created a rival municipal police force that clashed violently with the state authorities and state police.

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State investigations confirmed that there was widespread bribery and somehow he avoided conviction.

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His political machine maintained iron control over the city operations for years and years, decades in fact.

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Oh, and when you're talking about Fernando Wood, you have to include the guy gave in 1861 probably the most treasonous speech ever that I have been able to find by any sitting U.S.

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mayor of any city.

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So again, Fernando Wood is the controversial mayor of New York City, and this is during the tense early days of the Civil War.

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This guy delivers a very provocative address to the Common Council on January 6, 1861.

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It's often referred to as the secession speech.

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This is just weeks after the South Carolina had become the first state to secede from the Union.

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They did so in December of 1860.

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So with a nation fracturing over slavery and economic interest, Wood proposed to secede the city.

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I mean, I understand Fernando Wood is a staunch Democrat at the time.

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He's a pro-Southern sympathizer known as a copperhead.

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He argues that New York City should secede from both the New York State and the United States and become an independent, quote, free city.

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Does that sound as radical as the stuff we're hearing right now in 2025?

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He envisioned it, I guess, as a neutral republic modeled loosely after the ancient city-states like Venice or the Hazadic League, you know, free to trade with both the North and the seceding South without any disruptions of war or federal tariffs.

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And at the time, New York City is the nation's commercial powerhouse.

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It's handling over two-thirds of U.S.

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imports and relying heavily on Southern cotton for its shipping, banking, and textile industries.

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Now, the radical mayor points out that tariffs alone generated$56 million of the federal government's$64.6 million of revenue in 1860.

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Much of it is collected at New York's port.

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Secession, he claims, would let the city keep those funds and support its local government without taxing the residents.

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And then he could also maintain lucrative trade ties with a Confederacy.

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And the speech would frames the Union as a venal and corrupt master that has failed the city.

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He warns that Abraham Lincoln's impending presidency and the Republican anti-slave policies would ruin New York City's economy by cutting off Southern commerce.

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Now he acknowledged that the radical nature of his idea, and he notes that secession might subvert all federal authority.

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You don't think?

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So he dissolves the community into its original elements, but he insists that there should be a pragmatic response to his idea.

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He even suggests that the city could arm itself if needed to defend this independence.

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So he blends his economic self-interest with a call for home rule and a garnering of arms.

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Now the proposal wasn't entirely out of left field for Mr.

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Wood.

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As a three-time radical mayor from 1855 to 58, and then again from 1860 to 62, he was a Tammany Hall operative, just when Tammany Hall was getting its Tammany Hall two step, if you know what I mean.

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He had a long championed Southern interest, he opposed abolitionism, and he used patronage to build his machine politics on the backs of Irish immigrants and merchants.

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His brother Benjamin edited the pro-Confederate New York Daily news, just across town, which would later be shut down for treason.

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Shocking, I know.

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So the speech also highlighted Wood's progressive side, or radical side, as we should say.

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Public reaction was swift and polarized.

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The New York Times actually mocked it as laughable.

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They recommended a good laugh if you wanted to read it, but they also called pro-union rallies as treasonous as well.

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The Common Council debated, I can't even believe they did this, they debated the reaction to the speech, but they ultimately rejected the idea and tabled it amid growing unionist fervor in the city.

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Now, when Confederate forces fired on Fort Sumter in eight April of 1861, New York City erupted in patriotic support for the Union, and it completely overwhelmed secessionist voices like the mayor himself.

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Wood then pivoted and read the room and publicly backed the war effort to salvage his career.

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Though he did continue to oppose Lincoln and Congress, and he served several more multiple terms, and he fought the 13th Amendment that established slavery.

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Or that abolished slavery, rather.

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So in hindsight, you can see the radical mayor's speech underscores just how complex New York City's mayor role is.

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This guy lived in the Civil War, but he was a northern hub of southern economic entanglements, where class, immigration, and commerce fueled very divided loyalties.

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Thank God his crazy idea never came to fruition.

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But it did foreshadow, we should say.

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It did foreshadow the city's internal complex.

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And it was the backdrop in the context of the deadly draft riots of 1863.

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Now, Wood died in 1881.

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His legacy was a mix of bold, radical urban reforms and unapologetic political cynicism.

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So we're going to cover the draft riots in New York City of 1863 in another episode, but we wanted to give you the chilling and fascinating history of one of the corrupt and worst mayors in New York City history.

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Now, the third most corrupt of the New York City mayors was a person named A.

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Oakie Hall, Elegant Hall, as they called him.

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He was mayor from 1868 to 1872.

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He was a tweed ally and approved of the fraudulent contracts.

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He was indicted in 1871.

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He was ultimately acquitted, though.

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But historians view his tenure as either complicit or deliberately negligent beyond all repair.

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Now you got to fast forward all the way to the jazz age to find another corrupt mayor, James Jimmy Walker.

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He was mayor from 1926 to 1932.

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That guy accepted bribes in exchange for city contracts.

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We had the Seaberry investigation that revealed hidden bank accounts and direct payoffs.

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He ultimately resigned in 1932, left for Europe to evade prosecution.

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Then we come to the current mayor, Eric Adams.

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He was indicted in September of last year on federal charges of bribery, wire fraud, soliciting illegal foreign contributions tied to luxury travel benefits.

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He pleaded not guilty.

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The case still remains active.

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We're not sure if Mayor Adams is actually guilty.

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We think he just got on the wrong side of the most corrupt administration in U.S.

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presidential history, Joe Biden's administration.

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So we'll see how that how that case comes out.

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But the pattern going all the way back for the last 150 years plus is clear.

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Tammany Hall institutionalized patronage, vote buying, and graft for over a century in the democratic politics of New York City.

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It drained billions from the public coffers.

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Now, Zoran Mandani, he leads in the polls over Andrew Cuomo and Curtis Suilla in a deeply blue and democratic city.

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Mandami's agenda includes rent freezes, free child care, a$30 minimum wage by 2030, and new taxes on all billionaires and high earners.

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Now he positions himself as a pragmatic socialist.

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He cites Milwaukee's Daniel Hone as a model going all the way back to the early 20th century for Milwaukee's mayor.

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However, socialism, even in a moderated form, functions as a gateway to expanded state control and economic intervention.

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Mandami's foreign policy positions are beyond concerning.

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He has pledged to arrest Israeli Prime Minister Bibi Netanyahu if the ICC warrant is issued.

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That's the International Criminal Court.

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Now, this ignores the fact that the United States was never a signatory to this statute, and UN visitors and all of their delegates come back and forth to the United Nations and they all enjoy diplomatic immunity.

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So I'm not sure what Mr.

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Mandani is thinking there.

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I think he just got some bad advice.

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But he doesn't fall far from the tree, as they say.

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His father is a radical Columbia professor, Mahmoud Mandani.

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He's compared Israel to the apartheid in South Africa, and he defends aspects of Palestinian resistance.

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Zoran condemns anti-Semitism, but refuses to restrict speech, creating ambiguity around enforcement on public safety.

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He has taken a step back from his earlier defund the New York City police rhetoric.

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He's now advocating collaboration with the NYPD and pairing officers with social workers.

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Not sure how that's going to work.

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This shift may not prevent further officer departures amid the low morale in the NYPD.

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And they're certainly still having recruitment challenges.

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Now, Mr.

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Mandani has garnered some endorsements, endorsements from Mr.

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Hakeem Jeffries and progressive leaders from the squad, suggesting a broader and a broadening coalition.

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But his core agenda remains to the far left, the radical left.

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I would rate Mr.

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Mondani's radicalism on a nine out of ten scale.

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He's comparable to Fernando Wood's disruptive 1850s and 1860s tenure.

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Now, Wood, you'll remember, he was a wealthy Tommany, Tammany Hall demagogue.

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He won three terms by championing the Irish immigrants while engaging in corruption and defying state authority.

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In 1857, you won't believe this, he refused to recognize the state-created Metropolitan Police.

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That led to a riot at City Hall with over 50 officers injured.

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Mondani or uh not Mondani, but Fernando Wood actually created his own police force.

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Imagine that.

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New York City Mayor creates his own police force, his own thugs, as they say.

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Now, Fernando Wood would expand public transit and he preserved Central Park's size, and he blended progressive policies with machine politics.

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So what would Mr.

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Mandani do his first 100 days?

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Well, he's going to prioritize rent controls, fare free buses, and enhanced immigration protections, potentially in defiance of federal policy under a second Trump administration.

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That's going to be a problem.

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But Mr.

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Mandani, he emphasizes cultural inclusivity.

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He wants to accelerate Diwali.

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He wants to defend Muslim communities.

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And he aims to unify but risks alienating other groups.

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Now, as we've seen many times, that New York City often serves as a national bellwether.

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Mandani's potential win could signify a return to 19th century, 19th century style municipal socialism, expansive welfare paired with centralized power.

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We must ask, though.

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This model strengthens cities and repeats the failures of patronage and overreach.

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You know, beyond New York City, there's three additional races that we are paying attention to.

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Just across the river in New Jersey, Democrat Mike Mickey Sherrill is facing Republican Jack Cidarelli in a contest shaped up by property taxes and economic growth.

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The polls show a very tight race.

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Gender dividing those voters, and especially the suburban voters to the urban voters, as two ways to slice that polling.

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A chitterelli upset would mark the first Republican guomnatorial win since Chris Christie won the state back in 2010.

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In Virginia, Democrat Abigail Spanberger leads Republican Winsome Earl Sears in the governor's race, and Spanberger's CIA background and moderate positioning give her an edge, but that state has started to turn purple.

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Now, this would be the first all-female major party matchup for governor in Virginia's history.

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We still think that the Virginia Attorney General race pits him that pits incumbent Republican James Myris against Democrat Jay Jones.

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Jay Jones is the guy who's lying all about his text messages.

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Jones led in the early polls, but with those recently serviced text messages in which he joked, he joked about violence against Republican lawmaker and his family, that has triggered a severe backlash, and now a criminal investigation.

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So polls show a dead heat, making this race critical for control of the state law enforcement and legal policies.

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So these four contests New York City mayor, the New Jersey governor's race, the Virginia's governor's race, and the Virginia AG race will shape how criminal justice, economic policies, and cultural direction gives us for the next five to ten years.

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So with all that, we are going to pay close attention to all four of these races.

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We hope that Madani loses, that Chillarelli wins, that Winsome Sears wins, and that Myris wins in the Virginia AG spot.

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We want a clean sweep for all of the lesser forms of radicalism that we're seeing across four of these East Coast elections.

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That's today's mojo minute.

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We're going to stay vigilant, we're going to stay informed, and we will break down the results next week.

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As always, let's keep fighting the good fight.

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Thank you for joining us.

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We hope you enjoyed this theory to action podcast.

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Be sure to check out our show page at teammojocademy.com, where we have everything we discussed in this podcast as well as other great resources.

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Until next time, keep getting your emojoy.