We 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 Hyland. 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 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 Catskills.
A farm with a crushing mortgage. Right. How does
he arrive in the city with exactly three dollars
and 50 cents 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 monopolies 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. Hyland is
far more than just a quirky footnote. His life
offers this masterclass 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 machines.
Oh, absolutely. And most importantly, his entire
career illustrates that eternal friction between
working class... You know, the people who actually
lay the train tracks. Literally, in this case.
Literally. Yeah. 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 from
a rural background, but just how poor are we
talking here? We are talking about borderline
destitution. Wow. Yeah. Highland was born in
1868. in Hunter, New York, deep up in the Catskills.
His father was an Irish immigrant from County
Cavan 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 60 -acre farm that carried a crushing $1 ,500
mortgage. Which in the 1870s and 80s... That
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.
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 Catskill Railroad.
Doing brutal work. He was literally digging earth
and tamping it under the tracks to stabilize
them after the winter thaws. But by the winter
of 1887, when he's 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 downstate, and
just walks across the Brooklyn Bridge. Which
is an incredible visual. He arrives in Brooklyn
with $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 Catskills. He has never even
seen an elevated train before. 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 $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, anyone
who knows New York weather history knows exactly
what that date means. 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 principal 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
it. 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 his 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, Hyland 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 regents 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 Newark 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 was just shoveling coal in
a blizzard, sitting in a classroom, being lectured
by one of the premier academic minds of the era.
Here'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 upstate 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 Hyland 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 engineer's
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 mortgages
the family farm again. The same farm. The exact
same farm. He borrows $500 against it to open
a law firm on the corner of Gates Avenue and
Broadway in Bushwick. He partners with an attorney
named Harry C. Underhill. Underhill handles the
tedious paperwork, while Hyland acts as the fiery
trial lawyer. They made a good team. They did.
And they start taking on cases that matter to
everyday 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
companies. Exactly. Meanwhile, he's building
a political network, but he's not doing it at
fancy galas or backroom cigar clubs. Yeah. He
meets the future Democratic Party boss of Brooklyn,
John H. McCooey. entirely by accident. Just a
random encounter. McCooey was working as a postal
clerk at the time. Hyland was just a regular
guy coming in to buy postal money orders to pay
his parents' farm mortgage. Unbelievable. McCooey
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 Hyland actually
climbs the ladder to become mayor, you have to
understand the cutthroat machine politics of
1903 New York City. It 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 Tammany Hall
machine. Right. Murphy wanted to expand Tammany's
influence beyond Manhattan and into all the other
boroughs. To force the issue, Murphy decides
to push George B. McClellan Jr., the son of the
famous Civil War general, onto the Democratic
ticket for mayor. I imagine the Brooklyn political
bosses did not appreciate Manhattan trying to
run their borough. They fought it tooth and nail.
The Brooklyn bosses, Hugh McLaughlin and Patrick
H. McCarron, knew exactly what was at stake.
Patronage. Exactly. If Tammany 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 the
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 -Tammany ticket. Global chaos.
But Tammany Hall had the numbers. They absorbed
the abuse, smiled through it, and forced their
slate through anyway. The Brooklyn bosses had
to capitulate. In the chaotic aftermath, Patrick
H. McCarron takes control of the Brooklyn organization
and John Francis Hyland. 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 has shifted.
Hyland runs for mayor against the incumbent.
John Perroy 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. Hyland was the exact
opposite. He was the blunt instrument. Exactly.
Hyland gets backed by Tammany Hall. And crucially,
he secures the backing of the incredibly powerful
newspaper publisher William Randolph Hearst.
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 Hyland 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. Hyland was inadvertently building the
blueprint for modern urban political coalitions.
Oh, so? Well, the old political machines traditionally
relied almost exclusively on European immigrant
blocs. Yeah. The Irish, the Italians, the Germans.
They often ignored the growing black population.
Right. But Hyland'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. So 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 One, 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. Hyland deeply despised the private transit
trusts, specifically the Brooklyn Rapid Transit
Company and the Interboro Rapid Transit Company.
He hated them. Those private companies were financially
struggling and aggressively demanding the right.
to raise the subway fare from 5 cents to 7 or
8 cents. And Hyland absolutely refused to let
them raise that fare. To him, the 5 -cent fare
was a sacred pact with the working class. Absolutely
sacred. When the private companies threatened
to cut service, Hyland 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
wholly 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. Hyland 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 Hyland gets
up to the podium to deliver it, he completely
misreads the context of the writing. He reads
the year as individual digits. Oh 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 wince from his staff.
The city's elites never let him forget gaffes
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 more
finesse for the roaring 20s. So they run the
incredibly slick, charming state senator, James
J. Jimmy Walker, against Hyland in the Democratic
primary. And Walker was the quintessential jazz
age politician. Yeah. Witty, fashionable, and
completely comfortable in high society. Walker
defeats Hyland. 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.
When a journalist asked Walker why on earth he
would appoint his bitter rival to a children's
court, Walker quipped, the children now can be
tried by their peer. He is a devastating insult,
truly. But it's worth noting that despite the
jokes and the mockery, Hyland represented something
incredibly real. The elites laughed at his grammar,
but he swept Brooklyn Democrats into power. He
navigated the city through the chaotic post -WWI
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 in the Catskills. 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 out of
City Hall? So what does this all mean? How did
he view the systems of power once he was permanently
on the outside looking in? Hyland 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 interests 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 refused 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 are 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. Objectively, Hyland'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 Hyland'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 Catskills studying from a borrowed
history book. Shoveling 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 Tammany Hall machine politics
of the early 1900s. He becomes the mayor of New
York City, build a historic multiracial 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 inflect in his public speaking.
But to the people laying the tracks, working
the factories and paying the fares, he was one
of them. He understood their struggles because
he had physically endured them. Yeah. 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 for you to ponder as we wrap up. Consider
Highland's lifelong absolute obsession with keeping
the subway fare at exactly five cents. Today,
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 Hyland. you enjoyed
the ride and as always we invite you to keep
questioning the world around you