The Railroad Stoker Who Ran New York

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1:01We are so glad you're joining us for this deep dive. Yeah, we're really thrilled to have you here. Because today, we're opening up a comprehensive biographical article to explore a life that honestly, well, it almost defies belief. It really does. We are looking at the fascinating, highly unlikely, and honestly heavily mocked life of John Francis Red Mike Highland. The 97th mayor of New York City. Exactly. The guy who ran the town from 1918 to 1925. And our mission today isn't to just, you know, recite some dry timeline of mayoral accomplishments. Right. Nobody wants that. No. We want to show you the jarring contrast of this man's life. I mean, think about this for a second. How does a kid from a dirt poor 60 acre farm in the cat skills? A farm with a crushing mortgage. Right. How does he arrive in the city with exactly $3.50 to his name and then end up running the largest metropolis in America? It's a massive leap. It's insane. How does he accidentally pioneer a modern political coalition? Wage this absolute war on private transit

2:04monopolies and yet somehow get roasted by his own successor with, I mean, genuinely one of the most savage political insults in recorded history. It is a phenomenal trajectory. Yeah. And for anyone looking at this history, I think the real takeaway is that Highland is far more than just a quirky footnote. His life offers this master class in sheer unrelenting hustle and survival. But beyond that, it's a brilliant window into the raw bare knuckle mechanics of early 20th century political machine. Oh, absolutely. And most importantly, his entire career illustrates that eternal friction between working class populism. You know, the people who actually lay the train tracks literally, in this case, literally, yeah, rule and the polished, highly educated elite who generally expect to run the government. Okay, let's unpack this. We have to start with his incredibly rural beginnings because if you don't understand the farm, you don't understand the mayor. You really don't. I know he came rural background, but just how poor are we talking here? We are talking about borderline destitution.

3:05Wow. Yeah. Highland was born in 1868 in Hunter, New York, deep up in the cat skills. His father was an Irish immigrant from County, Kevin, who came over as a child and later fought in the Civil War as a corporal in the Ulster Regiment. Exactly. And his mother had Welsh and French roots. They were trying to survive on a 68 car farm that carried a crushing $1,500 mortgage, which in the 1870s and 80s. I was a mountain of debt. And they worked the land entirely with hand tools. The local school district was so severely impoverished and only ran five months out of the year. This is the part that gets me. Yeah, the school kids had to share a single history book. One book. Because only one family in the entire area could actually afford to buy it. Sharing a single textbook is a detail that just sticks with you. And as the oldest boy, the farm work naturally fell on his shoulders. Right. Before he was even out of his teens, he was making extra money to pay the interest on that family mortgage by working for the cat's girl railroad. Doing brutal work. He was literally digging earth and tamping it under the tracks

4:08to stabilize them after the winter thaws. But by the winter of 1887, when his 19, he realizes he needs to make real money to save his parents farm. So what does he do? He takes his entire life savings, $3.50, buys a $2 train ticket down state and just walks across the Brooklyn Bridge. Which is an incredible visual. He rides in Brooklyn with a $1.50 in his pocket. He looks up and sees construction on an elevated railroad. Just going on right there. Right. And keep in mind, this is a kid from the cat skills. He has never even seen an elevated train before. Ever. But he climbs right up the structure, tracks down the foreman, and essentially pesters the manager's office every single day until they give him an interview. To your hustle. He gets a job laying rails and eventually gets promoted to a fireman doing heavy physical labor for a $1.50 a day. And the working conditions were unimaginable by today's standards. He actually reported for duty at the East New York station on March 11, 1888. Yeah,

5:09anyone who knows New York weather history knows exactly what that date moves. The great blizzard of 1888. Exactly. He was working as a stoker, shoveling coal into a roaring furnace while enduring 13 hour runs on weekdays, 12 hours on Saturdays and 11 hours on Sundays through one of the worst storms in recorded history. Just brutal. But the grind pays off. He becomes an engineer making $3.50 a day. And he uses that money to completely pay off the principle of his parents farm mortgage. What's fascinating here is how this grueling physical railroad work forged his entire political identity. He wasn't a politician who read about the working class in a university library or someone who just deployed working class rhetoric to get votes. He was the working class. He lived. He lived it. That lack of polish, that blunt blue collar edge, it was completely authentic. And as we'll see, that background perfectly explains his later absolute obsession with keeping public transit cheap when he eventually takes control of the city. Yeah, that transition from the engine cab to the courtroom is a massive pivot. So he's married,

6:14his childhood sweetheart, Marion O'Hara, they're living in Bushwick, Brooklyn, and he's making $100 a month. Good money at the time. Right. He probably would have driven trains until he retired. But then tragedy strikes. His younger brother, who was studying law and carrying all the family's professional hopes, passes away, devastating, pushed by that grief. And with a lot of encouragement from his wife, Highland decides he is going to take up his brother's mantle and become a lawyer. But the guy doesn't even have a high school diploma. Right. He has to enroll in business school just to pass a region's exam so he can even apply to law school. But he manages to get into New York law school. Yeah. And the historical crossover here is just brilliant. I love this part. While he's at New York law school, taking a class on constitutional law, his professor is none other than future United States President Woodrow Wilson. That is wild to think about. You have a guy who is just shoveling coal and a blizzard sitting in a classroom being lectured by one of the premier academic minds of the era.

7:16Here's where it gets really interesting though. The story of his bar exam perfectly captures his resourcefulness. He graduates clerks for an attorney and needs to take the bar exam. But there's a catch. A huge catch. The earliest available test is all the way up state in Syracuse. And right before the exam, he gets into a near crash on the railroad with a supervisor. Oh, no. Yeah. And even though Highland blames the supervisor, he gets fired. So now he has no job and zero cash to buy a train ticket to Syracuse. So what does he do? Because he religiously kept paying his union dues. He flashes his locomotive engineers union pass rides the rails to Syracuse entirely for free and passes the bar. It's pure pragmatism. But now he's officially a lawyer and a law degree doesn't magically pay the rent. Nope. He needs startup capital to open a practice. So he mortgage is the family farm again. The same farm. The exact same farm. He borrow his $500 against it to open a law firm on the corner of Gates Avenue in Broadway in Bushwick. He partners with an attorney named Harry

8:21C. Underhill. Underhill handles the tedious paperwork while Highland acts as the fiery trial lawyer. They met a good team. They did. And they start taking on cases that matter to every day working class commuters. They actually win a massive ruling forcing the Brooklyn Heights railroad company to offer free transfers at all junctions. So he's already fighting the transit company. Exactly. Meanwhile, he's building a political network. But he's not doing it at fancy gallows or backroom cigar clubs. Yeah. He meets the future Democratic Party boss of Brooklyn, John H. McEwy, entirely by accident. Just a random encounter. McEwy was working as a postal clerk at the time. Highland was just a regular guy coming into by postal money orders to pay his parents farm mortgage. Unbelievable. McEwy was kind to him. They struck up a friendship. And that completely mundane interaction laid the foundation for his entire political rise to understand how a guy like Highland actually climbs the ladder to become mayor. You have to understand the cutthroat machine politics of 1903 New York City.

9:24It was like Game of Thrones. It really was. It was essentially a battle for total control of the city's resources. Over in Manhattan, you had Charles Francis Murphy, the powerful new head of the infamous Tamini Hall machine. Right. Murphy wanted to expand Tamini's influence beyond Manhattan and into all the other burrows to force the issue. Murphy decides to push George B. McClellan Jr. the son of the famous civil war general on to the Democratic ticket for mayor. I imagine the Brooklyn political bosses did not appreciate Manhattan trying to run their burrows. They fought at tooth and nail. The Brooklyn bosses, Hugh McLaughlin and Patrick H. McCarran knew exactly what was at stake patronage exactly if Tamini Hall got their mayor Murphy would use him to steal all of Brooklyn's patronage and patronage wasn't just abstract political influence. It meant thousands of literal city jobs street sweepers clerks inspectors and incredibly lucrative city contracts. Right. Those jobs were the currency they used to buy loyalty and guarantee votes. If they lost

10:25the patronage, they lost their power. It all came to a head at a massive convention at Carnegie Hall in October 1903. Blistering speeches, delegates howling each other down, threats of a completely separate anti-Tamini ticket. But Tamini Hall had the numbers. They absorbed the abuse, smiled through it and forced their slate through anyway. The Brooklyn bosses had to capitulate. Yeah. In the chaotic aftermath, Patrick H. McCarran takes control of the Brooklyn organization and John Francis Highland. He just keeps his head down and quietly makes his first moves for party advancement within that new reality, getting appointed to a magistrate position. He spends the next decade building his profile as a reliable loyal party man and a populist judge. Fast forward to 1917 and the political landscape is shifted. Highland runs for mayor against the incumbent, John Paroy Mitchell. The boy mayor. Right. Mitchell was known as the boy mayor. He was young, Ivy League educated, polished and a total darling of the wealthy reformers. Highland was the exact opposite. He was the blunt instrument. Exactly. Highland gets backed by Tamini Hall. And

11:31crucially, he secures the backing of the incredibly powerful newspaper publisher William Randolph Hurst. And he wins. The kid who shared a single history book becomes the mayor of the largest city in America. It's amazing. But there's a massive demographic milestone in that 1917 election that often gets overlooked. John Francis Highland was the first Democratic candidate to obtain a significant portion of the African-American voter base in New York City. If we connect this to the bigger picture, Highland was inadvertently building the blueprint for modern urban political coalitions. Oh, so? Well, the old political machines traditionally relied almost exclusively on European immigrant blocks. Yeah. The Irish, the Italians, the Germans, they often ignored the growing black population. Right. But Highland's blunt anti-elite messaging appealed to marginalized voters who felt entirely locked out by the polished aristocratic reformers like Mitchell. That shift signaled the very beginning of the broader multiracial working class coalitions that would eventually define 20th century democratic politics.

12:33So he gets into office and serves for eight years. What did he actually do with that power? He took office right at the end of World War I, which meant he was immediately dealing with severe post-war inflation, massive housing shortages, and labor strikes. A tough time to be mayor. But his defining battle, the thing that consumed his mayoralty, was the transit system. Highland deeply despised the private transit trusts, specifically the Brooklyn Rapid Transit Company and the Interborough Rapid Transit Company. He hated them. Those private companies were financially struggling and aggressively demanding the right to raise the subway fare from five cents to seven or eight cents. And Highland absolutely refused to let them raise that fare. To him, the five-cent fare was a sacred pact with the working class. Absolutely sacred. When the private companies threatened to cut service, Highland retaliated by aggressively pushing for a brand new massive public works project. The independent subway system or the ISS. A huge deal. He wanted a transit network,

13:34wholly owned and operated by the city, entirely free from the grip of private monopolies, ensuring the fare would stay at exactly five cents. But his aggressive tactics and blunt demeanor made him a massive target. Aside from William Randolph Hearst's papers, the entire city press corps, the wealthy elites, and the civic reformers hated him. Oh, they despised him. They considered him profoundly uneducated and mocked him relentlessly. And the historical anecdotes about his public blunders are just brutal. Highland had a reputation for just giving the exact same stump speech over and over aggressively yelling about the transit trusts and the five-cent fare, regardless of the occasion. Right. During one campaign, he asked a young Robert Moses to help him draft a fresh, inspiring speech. Moses obliges and writes a rousing patriotic climax. The speech was supposed to end with a dramatic soaring call to the spirit of 1776. But when Highland gets up to the podium to deliver it, he completely misreads the context of the writing. He reads the year as individual digits.

14:37Oh boy. He stands in front of a massive crowd and passionately yells, I call for the spirit of 1776. We can almost feel the collective wints from his staff. This city's elites never let him forget gas like that. And eventually, even his own political allies decided he was a liability. By 1925, Tammany Hall, led by Al Smith, decided they were done with Red Mike. They wanted someone with Morphin S for the roaring 20s. So they run the incredibly slick, charming state senator James James Jamie Walker against Highland in the Democratic primary. And Walker was the quintessential jazz age politician. Weedy, fashionable and completely comfortable in high society. Walker defeats Highland. But the ultimate burn comes shortly after. Walker, displaying a truly ruthless sense of political humor, appoints the defeated Highland to a judgeship on the Queen's Children's Court. Oh, what a journalist asked Walker why on earth, he would appoint his bitter rival to a children's court. Walker equipped. The children now can be tried by their peer is a devastating insult. Truly, but it's worth noting that despite the jokes in the mockery, Highland represented

15:41something incredibly real. The elites laughed at his grammar, but he swept Brooklyn Democrats into power. He navigated the city through the chaotic post W. W. I era and he broke the private transit monopolies. Yeah, he got things done. He genuinely represented the raw, unpolished masses against the refined sensibilities of the upper class. And you have to respect his ultimate pragmatism right at the very end of his tenure. He officially resigned from the mayoralty on December 30th, 1925. That was exactly one day before his second term was supposed to end. Why? Just to guarantee that he was legally eligible for a $4,205 annual pension from the city. A survivor to the end. Even after eight years of wielding immense power, he never forgot the financial insecurity of that farm and the cat skills he was securing his lifeline. So he secures his pension by resigning a day early, but a guy with this much populist fire doesn't just retire to a rocking chair. What does he do with his megaphone once he's at a city hall? So what does this all mean? How did he view the systems of power once he was permanently

16:46on the outside looking in? Highland spent his later years writing and speaking about the dangers of industrial concentration. He had given a very famous speech back in 1922 while he was still mayor that perfectly encapsulates his entire worldview. He warned the public that the real menace to the republic was an invisible government and invisible government. He described it as a giant octopus with slimy legs controlled by the Rockefeller standard oil interest and a small group of international bankers. He claimed this little coterie actually ran the government, controlled both political parties and used the mainstream newspapers to club public officials into submission if they refuse to do the bidding of corrupt big business. This raises an important question about how we analyze political rhetoric and I want to be very clear for everyone listening. We're exploring this deep dive not to endorse this specific viewpoint, but simply to convey the historical source material impartially. Absolutely. It's a historical artifact. Right. But it's fascinating to look at his 1922 speech

17:48objectively. Highland's rhetoric specifically targeted what he genuinely perceived as corporate monopolies and wealthy elites completely controlling the press, the courts, and the government infrastructure. It's a powerful image. It is. When you look at that, this very specific flavor of anti-elite populist rhetoric, this deep-seated fear of an invisible government pulling the strings from the shadows. It remains a highly persistent theme across the entire political spectrum today. You see it everywhere. You hear clear echoes of Highland's giant octopus in modern critiques of corporate lobbying and billionaire influence from the left. And you hear the exact same structural distrust in critiques of an entrenched deep state from the right. It is a fundamental recurring American political anxiety. It is the ultimate outsider's view of power spoken by a man who had actually sat at the absolute center of it. It's time to summarize this incredible journey. You have a dirt poor farm boy from the cat skills studying from a borrowed history book.

18:50Shuffling coal in a blizzard. He becomes a train engineer, shoveling coal through the great blizzard of 1888. He teaches himself enough to get into law school, sits in a classroom taught by Woodrow Wilson, and hustles his way through the brutal Tamini Hall machine politics of early 1900s. He becomes the mayor of New York City, build a historic multi-racial voter coalition, spends eight years fiercely battling private monopolies to protect a five cent subway fare, and then turns his sights on dismantling the invisible government. His life forces us to look at how we view political authenticity and class divides. It really does. The refined elites mocked his intellect in his public speaking. But to the people laying the tracks, working the factories, and paying the fairs, he was one of them. He understood their struggles because he had physically endured them. His lack of polish wasn't a liability to his voters. It was the ultimate proof that he hadn't been bought by the system. And that brings us to a final thought free to ponder as we wrap up. Consider Highlands lifelong absolute obsession with keeping the subway fare at exactly five cents.

19:53Today, we often view municipal infrastructure, transit budgets, zoning laws, toll roads, as dry, technocratic issues best left to economists and city planners. Right. Just numbers on a page. But for a guy who literally laid the steel tracks with his own hands and drove the trains through freezing storms, the price of a ticket wasn't a spreadsheet calculation. It was the ultimate visceral battleground for class equality. That's a great point. It makes you wonder, what is the modern equivalent of the five cent fare? What mundane everyday cost in our own lives, maybe the price of broadband internet or the hidden fees on a banking app is actually the invisible fault line of today's class struggles. It's a compelling question. And one that proves the arguments of the 1920s are still playing out in our daily lives. Thank you so much for joining us for this deep dive into the life of John Francis Highland. We hope you enjoyed the ride. And as always, we invite you to keep questioning the world around you. Warning, the following Zippercruder radio spot you are about to hear is going to be filled

20:56with F words. When you're hiring, we at Zippercruder know you can feel frustrated. For Lauren, even, like your efforts are futile and you can spend a fortune trying to find fabulous people only to get flooded with candidates who are just fine. Fortunately, Zippercruder figured out how to fix all that. And right now, you can try Zippercruder for free at zippercruder.com slash zippercruder, you can forget your frustrations because we find the right people for your roles fast, which is our absolute favorite effort. In fact, four out of five employers who post on Zippercruder get a quality candidate within the first day. Fantastic. So whether you need to hire four, 40 or 400 people, get ready to meet first rate talent. Just go to zippercruder.com slash zip to try Zippercruder for free. Don't forget that zippercruder.com slash zip. Finally, that zippercruder.com slash zip. Finding great candidates to hire can be like, well, trying to find a needle in a haystack. Sure, you can post your job to some job board,

22:00but then all you can do is hope the right person comes along, which is why you should try Zippercruder for free at zippercruder.com slash zip. Zippercruder doesn't depend on candidates finding you, it finds them for you. It's powerful technology identifies people with the right experience and actively invites them to apply to your job. You get qualified candidates fast. So while other companies might deliver a lot of hey, Zippercruder finds you what you're looking for. The needle in the haystack. See why four out of five employers who post a job on Zippercruder get a quality candidate within the first day. Zippercruder, the smartest way to hire, and right now you can try Zippercruder for free. That's right. Free at zippercruder.com slash zip. That zippercruder.com slash zip zippercruder.com slash zip.