WEBVTT

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We are so glad you're joining us for this deep

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dive. Yeah, we're really thrilled to have you

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here. Because today we're opening up a comprehensive

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biographical article to explore a life that honestly...

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Well, it almost defies belief. It really does.

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We are looking at the fascinating, highly unlikely,

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and honestly heavily mocked life of John Francis

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Red Mike Hyland. The 97th mayor of New York City.

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Exactly. The guy who ran the town from 1918 to

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1925. And our mission today isn't to just recite

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some dry... timeline of mayoral accomplishments.

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Right. Nobody wants that. No. We want to show

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you the jarring contrast of this man's life.

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I mean, think about this for a second. How does

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a kid from a dirt poor 60 acre farm in the Catskills.

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A farm with a crushing mortgage. Right. How does

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he arrive in the city with exactly three dollars

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and 50 cents to his name and then end up running

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the largest metropolis in America? It's a massive

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leap. It's insane. How does he accidentally pioneer

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a modern political coalition wage this absolute

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war on private transit monopolies and yet somehow

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get roasted by his own successor with I mean

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genuinely one of the most savage political insults

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in recorded history. It is a phenomenal trajectory.

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Yeah. And for anyone looking at this history

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I think the real takeaway is that. Hyland is

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far more than just a quirky footnote. His life

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offers this masterclass in sheer, unrelenting

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hustle and survival. But beyond that, it's a

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brilliant window into the raw, bare -knuckle

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mechanics of early 20th century political machines.

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Oh, absolutely. And most importantly, his entire

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career illustrates that eternal friction between

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working class... You know, the people who actually

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lay the train tracks. Literally, in this case.

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Literally. Yeah. And the polished, highly educated

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elite who generally expect to run the government.

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Okay, let's unpack this. We have to start with

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his incredibly rural beginnings because if you

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don't understand the farm, you don't understand

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the mayor. You really don't. I know he came from

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a rural background, but just how poor are we

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talking here? We are talking about borderline

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destitution. Wow. Yeah. Highland was born in

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1868. in Hunter, New York, deep up in the Catskills.

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His father was an Irish immigrant from County

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Cavan who came over as a child and later fought

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in the Civil War. As a corporal in the Ulster

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Regiment. Exactly. And his mother had Welsh and

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French roots. They were trying to survive on

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a 60 -acre farm that carried a crushing $1 ,500

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mortgage. Which in the 1870s and 80s... That

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was a mountain of debt. And they worked the land

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entirely with hand tools. The local school district

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was so severely impoverished and only ran five

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months out of the year. This is the part that

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gets me. Yeah, the school kids had to share a

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single history book. One book. Because only one

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family in the entire area could actually afford

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to buy it. Sharing a single textbook is a detail

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that just sticks with you. And as the oldest

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boy, the farm work naturally fell on his shoulders.

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Before he was even out of his teens, he was making

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extra money to pay the interest on that family

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mortgage by working for the Catskill Railroad.

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Doing brutal work. He was literally digging earth

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and tamping it under the tracks to stabilize

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them after the winter thaws. But by the winter

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of 1887, when he's 19, he realizes he needs to

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make real money to save his parents' farm. So

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what does he do? He takes his entire life savings,

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$3 .50, buys a $2 train ticket downstate, and

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just walks across the Brooklyn Bridge. Which

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is an incredible visual. He arrives in Brooklyn

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with $1 .50 in his pocket. He looks up and sees

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construction on an elevated railroad. Just going

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on right there. Right. And keep in mind, this

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is a kid from the Catskills. He has never even

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seen an elevated train before. But he climbs

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right up the structure, tracks down the foreman,

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and essentially pesters the manager's office

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every single day until they give him an interview.

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To your hustle. He gets a job laying rails and

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eventually gets promoted to a fireman doing heavy

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physical labor for $1 .50 a day. And the working

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conditions were unimaginable by today's standards.

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He actually reported for duty at the East New

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York Station on March 11, 1888. Yeah, anyone

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who knows New York weather history knows exactly

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what that date means. The Great Blizzard of 1888.

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Exactly. He was working as a stoker, shoveling

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coal into a roaring furnace while enduring 13

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-hour runs on weekdays, 12 hours on Saturdays,

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and 11 hours on Sundays through one of the worst

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storms in recorded history. Just brutal. But

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the grind pays off. He becomes an engineer making

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$3 .50 a day, and he uses that money to completely

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pay off the principal of his parents' farm mortgage.

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What's fascinating here is how this grueling

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physical railroad work forged... his entire political

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identity. He wasn't a politician who read about

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the working class in a university library or

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someone who just deployed working class rhetoric

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to get votes. He was the working class. He lived

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it. He lived it. That lack of polish, that blunt

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blue collar edge, it was completely authentic.

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And as we'll see, that background perfectly explains

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his later absolute obsession with keeping public

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transit cheap when he eventually takes control

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of the city. Yeah, that transition from the engine

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cab to the courtroom is a massive pivot. So he's

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married his childhood sweetheart, Marion O 'Hara.

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They're living in Bushwick, Brooklyn, and he's

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making $100 a month. Good money at the time.

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Right. He probably would have driven trains until

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he retired. But then tragedy strikes. His younger

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brother, who was studying law and carrying all

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the family's professional hopes, passes away.

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Devastating. Pushed by that grief, and with a

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lot of encouragement from his wife, Hyland decides

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he is going to take up his brother's mantle and

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become a lawyer. But the guy doesn't even have

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a high school diploma. Right. He has to enroll

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in business school just to pass a regents exam

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so he can even apply to law school. But he manages

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to get into New York law school. Yeah. And the

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historical crossover here is just brilliant.

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I love this part. While he's at Newark Law School

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taking a class on constitutional law, his professor

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is none other than future United States President

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Woodrow Wilson. That is wild to think about.

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You have a guy who was just shoveling coal in

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a blizzard, sitting in a classroom, being lectured

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by one of the premier academic minds of the era.

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Here's where it gets really interesting, though.

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The story of his bar exam perfectly captures

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his resourcefulness. He graduates, clerks for

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an attorney, and needs to take the bar exam.

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But there's a catch. A huge catch. The earliest

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available test is all the way upstate in Syracuse.

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And right before the exam, he gets into a near

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crash on the railroad with a supervisor. Oh,

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no. Yeah, and even though Hyland blames the supervisor,

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he gets fired. So now he has no job and zero

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cash to buy a train ticket to Syracuse. So what

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does he do? Because he religiously kept paying

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his union dues, he flashes his locomotive engineer's

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union pass, rides the rails to Syracuse entirely

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for free, and passes the bar. It's pure pragmatism.

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But now he's officially a lawyer, and a law degree

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doesn't magically pay the rent. Nope. He needs

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startup capital to open a practice, so he mortgages

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the family farm again. The same farm. The exact

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same farm. He borrows $500 against it to open

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a law firm on the corner of Gates Avenue and

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Broadway in Bushwick. He partners with an attorney

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named Harry C. Underhill. Underhill handles the

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tedious paperwork, while Hyland acts as the fiery

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trial lawyer. They made a good team. They did.

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And they start taking on cases that matter to

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everyday working class commuters. They actually

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win a massive ruling forcing the Brooklyn Heights

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Railroad Company to offer free transfers at all

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junctions. So he's already fighting the transit

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companies. Exactly. Meanwhile, he's building

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a political network, but he's not doing it at

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fancy galas or backroom cigar clubs. Yeah. He

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meets the future Democratic Party boss of Brooklyn,

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John H. McCooey. entirely by accident. Just a

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random encounter. McCooey was working as a postal

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clerk at the time. Hyland was just a regular

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guy coming in to buy postal money orders to pay

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his parents' farm mortgage. Unbelievable. McCooey

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was kind to him, they struck up a friendship,

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and that completely mundane interaction laid

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the foundation for his entire political rise.

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To understand how a guy like Hyland actually

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climbs the ladder to become mayor, you have to

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understand the cutthroat machine politics of

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1903 New York City. It was like Game of Thrones.

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It really was. It was essentially a battle for

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total control of the city's resources. Over in

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Manhattan, you had Charles Francis Murphy, the

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powerful new head of the infamous Tammany Hall

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machine. Right. Murphy wanted to expand Tammany's

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influence beyond Manhattan and into all the other

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boroughs. To force the issue, Murphy decides

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to push George B. McClellan Jr., the son of the

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famous Civil War general, onto the Democratic

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ticket for mayor. I imagine the Brooklyn political

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bosses did not appreciate Manhattan trying to

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run their borough. They fought it tooth and nail.

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The Brooklyn bosses, Hugh McLaughlin and Patrick

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H. McCarron, knew exactly what was at stake.

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Patronage. Exactly. If Tammany Hall got their

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mayor, Murphy would use him to steal all of Brooklyn's

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patronage. And patronage wasn't just abstract

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political influence. It meant thousands of literal

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city jobs, street sweepers, clerks, inspectors.

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And incredibly lucrative city contracts. Right.

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Those jobs were the currency they used to buy

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loyalty and guarantee votes. If they lost the

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patronage, they lost their power. It all came

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to a head at a massive convention at Carnegie

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Hall in October 1903. Blistering speeches, delegates

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howling each other down, threats of a completely

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separate anti -Tammany ticket. Global chaos.

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But Tammany Hall had the numbers. They absorbed

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the abuse, smiled through it, and forced their

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slate through anyway. The Brooklyn bosses had

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to capitulate. In the chaotic aftermath, Patrick

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H. McCarron takes control of the Brooklyn organization

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and John Francis Hyland. He just keeps his head

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down and quietly makes his first moves for party

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advancement within that new reality, getting

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appointed to a magistrate position. He spends

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the next decade building his profile as a reliable,

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loyal party man and a populist judge. Fast forward

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to 1917 and the political landscape has shifted.

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Hyland runs for mayor against the incumbent.

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John Perroy Mitchell. The boy mayor. Right. Mitchell

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was known as the boy mayor. He was young, Ivy

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League educated, polished, and a total darling

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of the wealthy reformers. Hyland was the exact

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opposite. He was the blunt instrument. Exactly.

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Hyland gets backed by Tammany Hall. And crucially,

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he secures the backing of the incredibly powerful

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newspaper publisher William Randolph Hearst.

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And he wins. The kid who shared a single history

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book becomes the mayor of the largest city in

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America. It's amazing. But there's a massive

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demographic milestone in that 1917 election that

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often gets overlooked. John Francis Hyland was

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the first Democratic candidate to obtain a significant

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portion of the African -American voter base in

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New York City. If we connect this to the bigger

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picture. Hyland was inadvertently building the

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blueprint for modern urban political coalitions.

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Oh, so? Well, the old political machines traditionally

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relied almost exclusively on European immigrant

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blocs. Yeah. The Irish, the Italians, the Germans.

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They often ignored the growing black population.

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Right. But Hyland's blunt anti -elite messaging

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appealed to marginalized voters who felt entirely

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locked out by the polished aristocratic reformers

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like Mitchell. That shift signaled the very beginning

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of the broader multiracial working class coalitions

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that would eventually define 20th century democratic

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politics. So he gets into office and serves for

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eight years. What did he actually do with that

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power? He took office right at the end of World

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War One, which meant he was immediately dealing

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with severe post -war inflation, massive housing

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shortages and labor strikes. A tough time to

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be mayor. But his defining battle, the thing

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that consumed his mayoralty, was the transit

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system. Hyland deeply despised the private transit

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trusts, specifically the Brooklyn Rapid Transit

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Company and the Interboro Rapid Transit Company.

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He hated them. Those private companies were financially

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struggling and aggressively demanding the right.

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to raise the subway fare from 5 cents to 7 or

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8 cents. And Hyland absolutely refused to let

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them raise that fare. To him, the 5 -cent fare

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was a sacred pact with the working class. Absolutely

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sacred. When the private companies threatened

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to cut service, Hyland retaliated by aggressively

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pushing for a brand new, massive public works

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project, the Independent Subway System, or the

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ISS. A huge deal. He wanted a transit network

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wholly owned and operated by the city, entirely

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free from the grip of private monopolies, ensuring

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the fare would stay at exactly five cents. But

00:12:42.250 --> 00:12:44.690
his aggressive tactics and blunt demeanor made

00:12:44.690 --> 00:12:48.090
him a massive target. Aside from William Randolph

00:12:48.090 --> 00:12:51.110
Hearst's papers, the entire city press corps,

00:12:51.370 --> 00:12:54.070
the wealthy elites, and the civic reformers hated

00:12:54.070 --> 00:12:56.809
him. Oh, they despised him. They considered him

00:12:56.809 --> 00:13:00.009
profoundly uneducated and mocked him relentlessly.

00:13:00.750 --> 00:13:03.029
And the historical anecdotes about his public

00:13:03.029 --> 00:13:06.269
blunders are just brutal. Hyland had a reputation

00:13:06.269 --> 00:13:08.730
for just giving the exact same stump speech over

00:13:08.730 --> 00:13:11.509
and over, aggressively yelling about the transit

00:13:11.509 --> 00:13:13.950
trusts and the five cent fare, regardless of

00:13:13.950 --> 00:13:15.870
the occasion. Right. During one campaign, he

00:13:15.870 --> 00:13:18.549
asked a young Robert Moses to help him draft

00:13:18.549 --> 00:13:22.070
a fresh, inspiring speech. Moses obliges and

00:13:22.070 --> 00:13:25.250
writes a rousing patriotic climax. The speech

00:13:25.250 --> 00:13:27.289
was supposed to end with a dramatic, soaring

00:13:27.289 --> 00:13:31.279
call to the spirit of 1776. But when Hyland gets

00:13:31.279 --> 00:13:33.259
up to the podium to deliver it, he completely

00:13:33.259 --> 00:13:35.759
misreads the context of the writing. He reads

00:13:35.759 --> 00:13:38.480
the year as individual digits. Oh boy. He stands

00:13:38.480 --> 00:13:40.100
in front of a massive crowd and passionately

00:13:40.100 --> 00:13:43.120
yells, I call for the spirit of 1776. We can

00:13:43.120 --> 00:13:45.059
almost feel the collective wince from his staff.

00:13:45.259 --> 00:13:47.720
The city's elites never let him forget gaffes

00:13:47.720 --> 00:13:50.500
like that. And eventually, even his own political

00:13:50.500 --> 00:13:55.000
allies decided he was a liability. By 1925, Tammany

00:13:55.000 --> 00:13:58.139
Hall led by Al Smith, decided they were done

00:13:58.139 --> 00:14:00.179
with Red Mike. They wanted someone with more

00:14:00.179 --> 00:14:02.500
finesse for the roaring 20s. So they run the

00:14:02.500 --> 00:14:05.440
incredibly slick, charming state senator, James

00:14:05.440 --> 00:14:07.720
J. Jimmy Walker, against Hyland in the Democratic

00:14:07.720 --> 00:14:10.539
primary. And Walker was the quintessential jazz

00:14:10.539 --> 00:14:13.740
age politician. Yeah. Witty, fashionable, and

00:14:13.740 --> 00:14:15.840
completely comfortable in high society. Walker

00:14:15.840 --> 00:14:18.759
defeats Hyland. But the ultimate burn comes shortly

00:14:18.759 --> 00:14:21.840
after. Walker, displaying a truly ruthless sense

00:14:21.840 --> 00:14:24.360
of political humor, appoints the defeated Highland

00:14:24.360 --> 00:14:26.620
to a judgeship on the Queen's Children's Court.

00:14:27.019 --> 00:14:29.919
When a journalist asked Walker why on earth he

00:14:29.919 --> 00:14:31.840
would appoint his bitter rival to a children's

00:14:31.840 --> 00:14:34.159
court, Walker quipped, the children now can be

00:14:34.159 --> 00:14:36.379
tried by their peer. He is a devastating insult,

00:14:36.559 --> 00:14:39.080
truly. But it's worth noting that despite the

00:14:39.080 --> 00:14:41.220
jokes and the mockery, Hyland represented something

00:14:41.220 --> 00:14:44.019
incredibly real. The elites laughed at his grammar,

00:14:44.039 --> 00:14:46.460
but he swept Brooklyn Democrats into power. He

00:14:46.460 --> 00:14:49.100
navigated the city through the chaotic post -WWI

00:14:49.100 --> 00:14:51.740
era, and he broke the private transit monopolies.

00:14:52.090 --> 00:14:54.629
Yeah, he got things done. He genuinely represented

00:14:54.629 --> 00:14:58.250
the raw, unpolished masses against the refined

00:14:58.250 --> 00:15:00.870
sensibilities of the upper class. And you have

00:15:00.870 --> 00:15:03.289
to respect his ultimate pragmatism right at the

00:15:03.289 --> 00:15:05.669
very end of his tenure. He officially resigned

00:15:05.669 --> 00:15:09.429
from the mayoralty on December 30th, 1925. That

00:15:09.429 --> 00:15:12.090
was exactly one day before his second term was

00:15:12.090 --> 00:15:15.120
supposed to end. Why? just to guarantee that

00:15:15.120 --> 00:15:19.059
he was legally eligible for a $4 ,205 annual

00:15:19.059 --> 00:15:21.860
pension from the city. A survivor to the end.

00:15:22.000 --> 00:15:24.799
Even after eight years of wielding immense power,

00:15:25.059 --> 00:15:27.620
he never forgot the financial insecurity of that

00:15:27.620 --> 00:15:30.059
farm in the Catskills. He was securing his lifeline.

00:15:30.259 --> 00:15:32.639
So he secures his pension by resigning a day

00:15:32.639 --> 00:15:35.179
early. But a guy with this much populist fire

00:15:35.179 --> 00:15:38.419
doesn't just retire to a rocking chair. What

00:15:38.419 --> 00:15:40.740
does he do with his megaphone once he's out of

00:15:40.740 --> 00:15:43.769
City Hall? So what does this all mean? How did

00:15:43.769 --> 00:15:46.250
he view the systems of power once he was permanently

00:15:46.250 --> 00:15:49.389
on the outside looking in? Hyland spent his later

00:15:49.389 --> 00:15:51.769
years writing and speaking about the dangers

00:15:51.769 --> 00:15:54.710
of industrial concentration. He had given a very

00:15:54.710 --> 00:15:57.970
famous speech back in 1922 while he was still

00:15:57.970 --> 00:16:01.350
mayor that perfectly encapsulates his entire

00:16:01.350 --> 00:16:04.490
worldview. He warned the public that the real

00:16:04.490 --> 00:16:07.230
menace to the republic was an invisible government.

00:16:07.509 --> 00:16:09.769
And invisible government. He described it as

00:16:09.769 --> 00:16:12.690
a giant octopus with slimy legs, controlled by

00:16:12.690 --> 00:16:15.049
the Rockefeller Standard Oil interests and a

00:16:15.049 --> 00:16:17.929
small group of international bankers. He claimed

00:16:17.929 --> 00:16:20.070
this little coterie actually ran the government,

00:16:20.330 --> 00:16:23.070
controlled both political parties, and used the

00:16:23.070 --> 00:16:25.409
mainstream newspapers to club public officials

00:16:25.409 --> 00:16:27.750
into submission if they refused to do the bidding

00:16:27.750 --> 00:16:30.909
of corrupt big business. This raises an important

00:16:30.909 --> 00:16:33.190
question about how we analyze. political rhetoric.

00:16:33.370 --> 00:16:35.049
And I want to be very clear for everyone listening.

00:16:35.169 --> 00:16:37.789
We are exploring this deep dive not to endorse

00:16:37.789 --> 00:16:40.190
this specific viewpoint, but simply to convey

00:16:40.190 --> 00:16:43.750
the historical source material impartially. Absolutely.

00:16:43.850 --> 00:16:46.289
It's a historical artifact. Right. But it's fascinating

00:16:46.289 --> 00:16:50.039
to look at his 1922 speech. Objectively, Hyland's

00:16:50.039 --> 00:16:52.399
rhetoric specifically targeted what he genuinely

00:16:52.399 --> 00:16:54.919
perceived as corporate monopolies and wealthy

00:16:54.919 --> 00:16:57.500
elites completely controlling the press, the

00:16:57.500 --> 00:16:59.399
courts, and the government infrastructure. It's

00:16:59.399 --> 00:17:02.019
a powerful image. It is. When you look at that,

00:17:02.059 --> 00:17:06.480
this very specific flavor of anti -elite populist

00:17:06.480 --> 00:17:09.180
rhetoric, this deep -seated fear of an invisible

00:17:09.180 --> 00:17:11.779
government pulling the strings from the shadows.

00:17:12.269 --> 00:17:15.190
It remains a highly persistent theme across the

00:17:15.190 --> 00:17:17.630
entire political spectrum today. You see it everywhere.

00:17:17.910 --> 00:17:21.470
You hear clear echoes of Hyland's giant octopus

00:17:21.470 --> 00:17:24.410
in modern critiques of corporate lobbying and

00:17:24.410 --> 00:17:26.569
billionaire influence from the left. And you

00:17:26.569 --> 00:17:30.589
hear the exact same structural distrust in critiques

00:17:30.589 --> 00:17:32.910
of an entrenched deep state from the right. It

00:17:32.910 --> 00:17:35.009
is a fundamental recurring American political

00:17:35.009 --> 00:17:38.089
anxiety. It is the ultimate outsider's view of

00:17:38.089 --> 00:17:40.890
power. Spoken by a man who had actually sat at

00:17:40.890 --> 00:17:43.769
the absolute center of it. It's time to summarize

00:17:43.769 --> 00:17:46.630
this incredible journey. You have a dirt poor

00:17:46.630 --> 00:17:49.390
farm boy from the Catskills studying from a borrowed

00:17:49.390 --> 00:17:51.809
history book. Shoveling coal in a blizzard. He

00:17:51.809 --> 00:17:53.990
becomes a train engineer shoveling coal through

00:17:53.990 --> 00:17:56.680
the great blizzard of 1888. He teaches himself

00:17:56.680 --> 00:17:58.940
enough to get into law school, sits in a classroom

00:17:58.940 --> 00:18:01.200
taught by Woodrow Wilson and hustles his way

00:18:01.200 --> 00:18:03.579
through the brutal Tammany Hall machine politics

00:18:03.579 --> 00:18:06.420
of the early 1900s. He becomes the mayor of New

00:18:06.420 --> 00:18:09.539
York City, build a historic multiracial voter

00:18:09.539 --> 00:18:12.900
coalition, spends eight years fiercely battling

00:18:12.900 --> 00:18:15.440
private monopolies to protect a five cent subway

00:18:15.440 --> 00:18:18.619
fare, and then turns his sights on dismantling

00:18:18.619 --> 00:18:21.829
the invisible government. His life forces us

00:18:21.829 --> 00:18:24.130
to look at how we view political authenticity

00:18:24.130 --> 00:18:27.369
and class divides. It really does. The refined

00:18:27.369 --> 00:18:30.109
elites mocked his inflect in his public speaking.

00:18:30.269 --> 00:18:32.549
But to the people laying the tracks, working

00:18:32.549 --> 00:18:35.029
the factories and paying the fares, he was one

00:18:35.029 --> 00:18:37.069
of them. He understood their struggles because

00:18:37.069 --> 00:18:39.170
he had physically endured them. Yeah. His lack

00:18:39.170 --> 00:18:41.650
of polish wasn't a liability to his voters. It

00:18:41.650 --> 00:18:43.630
was the ultimate proof that he hadn't been bought

00:18:43.630 --> 00:18:45.730
by the system. And that brings us to a final

00:18:45.730 --> 00:18:48.089
thought for you to ponder as we wrap up. Consider

00:18:48.089 --> 00:18:51.029
Highland's lifelong absolute obsession with keeping

00:18:51.029 --> 00:18:53.869
the subway fare at exactly five cents. Today,

00:18:53.950 --> 00:18:56.390
we often view municipal infrastructure, transit

00:18:56.390 --> 00:19:00.589
budgets, zoning laws, toll roads as dry technocratic

00:19:00.589 --> 00:19:03.650
issues best left to economists and city planners.

00:19:03.849 --> 00:19:06.029
Right. Just numbers on a page. But for a guy

00:19:06.029 --> 00:19:08.289
who literally laid the steel tracks with his

00:19:08.289 --> 00:19:10.390
own hands and drove the trains through freezing

00:19:10.390 --> 00:19:13.289
storms, the price of a ticket wasn't a spreadsheet

00:19:13.289 --> 00:19:16.970
calculation. It was the ultimate visceral battleground.

00:19:17.130 --> 00:19:19.930
for class equality. That's a great point. It

00:19:19.930 --> 00:19:21.710
makes you wonder, what is the modern equivalent

00:19:21.710 --> 00:19:25.309
of the five -cent fare? What mundane everyday

00:19:25.309 --> 00:19:28.869
cost in our own lives, maybe the price of broadband

00:19:28.869 --> 00:19:31.930
internet or the hidden fees on a banking app,

00:19:32.069 --> 00:19:35.309
is actually the invisible fault line of today's

00:19:35.309 --> 00:19:37.430
class struggles? It's a compelling question,

00:19:37.630 --> 00:19:40.390
and one that proves the arguments of the 1920s

00:19:40.390 --> 00:19:42.430
are still playing out in our daily lives. Thank

00:19:42.430 --> 00:19:44.150
you so much for joining us for this deep dive

00:19:44.150 --> 00:19:46.650
into the life of John Francis Hyland. you enjoyed

00:19:46.650 --> 00:19:49.170
the ride and as always we invite you to keep

00:19:49.170 --> 00:19:50.829
questioning the world around you