Welcome to the Deep Dive. We are taking a look
today at a story that operates as equal parts
political thriller, historical comedy, and just
a masterclass in pure unadulterated hustle. Yeah,
I mean, it's one of those historical narratives
that feels almost too cinematic to be real, you
know, yet it shaped the very foundations of the
country's largest city. Right. And our mission
for you today is to extract a roadmap of how
power is actually built, how it's lost, and how
it is ultimately remembered in a major metropolis.
Exactly. We are basing this deep dive on a single,
incredibly dense source. It's a comprehensive
Wikipedia article detailing the life of John
Francis Hyland. The 97th mayor of New York City.
Yep, the 97th and the 7th since the consolidation
of the five boroughs. But we aren't just reading
you a dusty biography today. We're looking at
the mechanics of political machines. Oh, very
dramatic. Right. And a man who went toe -to -toe
with the intellectual elite of his day. Okay,
let's unpack this. Before he was the mayor, before
he was a judge, he was known simply as Red Mike.
Red Mike, which paints a picture of a scrappy
fighter, which is a pretty accurate baseline
for understanding him. For sure. He was a man
who started with absolutely nothing. took on
what he called the interests, and left a legacy
tangled in monumental infrastructure projects
and, well, really cruel political punchlines.
If you look at his origins in the Catskill Mountains
around 1868, it's the classic immigrant grit
story. But I really want to understand the scale
of it. How does a kid from Hunter, New York,
with barely any resources, even begin a trajectory
towards City Hall? You really have to look at
the sheer economic anxiety that defined his youth.
His father was an Irish immigrant from County
Cabin who came over at age seven. Right. And
the father actually ended up fighting in the
Civil War as a corporal in the 120th New York
Infantry. Which was known as the Ulster Regiment,
right? Exactly. The Ulster Regiment. And his
mother, conversely, had these deep American roots.
Her grandfather fought in the American Revolution
alongside Lafayette. Wow. So there's this intense
blend of immigrant hustle and patriotic legacy
right from the start. Definitely. But despite
that heritage. The family was dirt poor. I mean,
they were strapped to a 60 -acre farm with a
$1 ,500 mortgage. Which in the 1870s and 80s
was a massive financial weight to carry. A crushing
weight. They struggled just to pay the semiannual
interest on it. As the oldest boy of five children,
Hyland's life was consumed by farm labor using
primitive hand tools. Just back -breaking stuff.
Yeah, and education was treated as a distant
luxury. The local school district was so impoverished
that only one family could afford the required
grammar or history book. Wait, one family in
the whole district? One family. Hyland had to
borrow this single book just to learn. He was
only getting about four to five hours of schooling
a day for just five months out of the year. Because
the farm demanded the rest of his time. Right.
And he was already doing side hustles as a teenager,
wasn't he? The source mentions him working on
a local railroad before he ever left the mountains.
He was. Every spring, he'd go work for the Catskill
Railroad. He was literally digging earth and
tamping it beneath the tracks to stabilize them
after the winter freezes. It's just raw manual
labor. Exactly. And sending every penny back
to help his parents pay that mortgage interest.
But by the winter of 1887, when he's 19 years
old, he realizes the math just isn't working
out. The farm just wasn't making enough. No.
So he figures he can make more money for the
family if he heads downstate. So he leaves the
Catskills and heads to Brooklyn. But I read he
only had something like $3 to his name. How does
a teenager with no money and a grade school education
even get a foot in the door in 1880s New York?
Well, he left the mountains with exactly $3 .50
in his pocket. Incredible. He spends $2 on a
train ticket, walks across the Brooklyn Bridge,
and immediately starts looking for leverage.
Just hits the ground running. The very first
day he arrives, he sees construction happening
on an elevated railroad. Having never even seen
an elevated structure before, he literally climbs
up onto the tracks, tracks down the foreman,
and leverages his brief manual labor experience
on the Catskill Railroad to ask for a job. Just
walking up and demanding a job, that takes some
serious nerve. It does. And the foreman tells
him to show up the next day to lay rails. But
he doesn't stop at laying rails. Our source notes
he actively campaigned for a promotion almost
immediately. Oh, he was relentless. He went to
the office of the manager of the Brooklyn Union
Elevated Railroad every single day. Every single
day. Every day. He badgered the management until
they finally gave him an interview and promoted
him to a fireman, which involved incredibly heavy
labor for $1 .50 a day. Still pretty low wages.
Yeah, but here is the crazy part. The timing
of this is legendary. His first day reporting
to the East New York station as a fireman was
March 11, 1888. Oh, wow. That is the exact day
of the Great Blizzard. The Blizzard of 88. That
was one of the most severe snowstorms in American
history. Starting a grueling outdoor physical
labor job on that specific day is wild. And he
pushed through it. After two years of being a
stoker and an engine hustler, he passed a test
and became a locomotive engineer, making $3 .50
a day. Which was a big step up. It was, but it
required brutal hours. We're talking 13 hour
runs on weekdays, 12 hours on Saturdays and 11
hours on Sundays. What's fascinating here is
how he utilized that time. He wasn't just surviving
that 13 hour a day grind. He was incredibly systematic
about his financial goals. Very systematic. While
working as a motorman, he regularly made the
$75 semi -annual interest payments for his family's
farm back upstate. Yeah. And he actually managed
to pay off the entire principal before he ever
left the railroad job. It's a huge accomplishment.
He even went back to Hunter, married his childhood
sweetheart, Marion O 'Hara, and moved her to
Bushwick in Brooklyn. He later wrote that once
he was making $100 a month, he had zero inclination
to seek any other position. He thought he had
made it. He had achieved his version of the American
dream. But then a tragedy completely altered
his trajectory. Right. His younger brother, who
was studying law and upon whom the family had
pinned all their hopes for upward mobility, passed
away. That's devastating. It was. And that loss
became the catalyst for Hyland to pursue a career
in law himself, basically to pick up the mantle
for his family. But remember, he barely had a
grade school education. To pivot to law, he had
to do massive amounts of catch up. He had to
go to the Long Island Business College just to
prepare for the regents exams. Right. For those
of you listening who might not be familiar with
the New York education system of that era, the
regents exams were the standardized state tests
required to prove high school level competency.
You couldn't just walk into a law school without
passing them. And he needed a lot of help to
get there. He had a teacher who actually gave
up his lunch hours to help highlight. and study
for those exams. Which is such a great detail.
It is. And as a quick aside, it became a great
example of political loyalty later on. When Hyland
eventually became mayor, he rewarded that exact
teacher with a comfortable city job in the Department
of Water Supply. Gotta reward your base. So once
he passes the regents exams, he enrolls in New
York Law School. And there is an incredible historical
detail hidden in his time there. One of his professors
for constitutional law was none other than Woodrow
Wilson. It's almost hard to believe. The future
mayor of New York being taught by the future
president of the United States. It really highlights
how concentrated the circles of influence were
becoming, even for a guy who started out tamping
dirt under railroad ties. But here's where it
gets really interesting. Hyland graduates in
October 1897 and clerks for a Long Island city
attorney. He's ready to take the bar exam, but
the earliest one available is all the way up
in Syracuse. Yeah, nowhere near Brooklyn. Right
before he's supposed to go, he gets into a near
accident with a railroad supervisor. Hyland claims
it was the supervisor's fault, but he gets fired
from the railroad anyway. Typical. So he's out
of a job, he needs to get to Syracuse, and he's
tight on cash. What does he do? He brilliantly
uses his membership pass from the Brotherhood
of Locomotive Engineers to travel the rails for
free up to Syracuse. He takes the exam and he
passes. Passing the bar is only step one, though.
He quickly realized that starting a law practice
required upfront capital, something he no longer
had without his railroad salary. So what's his
move? Well, in a massive gamble, he mortgages
the family farm back in the Catskills again.
Oh man, after spending all those years paying
it off. Exactly. This time he mortgages it for
$500 to open an office on the corner of Gates
Avenue and Broadway in Bushwick. And he forms
a partnership with an attorney named Harry C.
Underhill. Underhill did the office work and
wrote legal treatises while Hyland became the
trial lawyer. Iredi only made $24 his first month,
taking on small civil cases and family law. Slow
start. Yeah, but he was highly strategic about
the cases he took. He wasn't trying to mingle
with corporate titans. He knew his power base
was the working class of Brooklyn. He took on
cases that mattered to everyday commuters. His
firm famously won a ruling that forced the Brooklyn
Heights Railroad Company to offer free transfers
at all junctions. That's huge. It might sound
like a minor administrative victory today, but
for a working class family in Brooklyn at the
turn of the century, a second transit fare could
literally break the weekly budget. Absolutely.
Winning that case got him incredible local publicity
and really solidified his reputation as a champion
of the common writer. Alongside his legal work,
he was relentlessly networking. He kept his union
membership active, joined the Foresters of America,
the Broadway Board of Trade, the Local Taxpayer
Association, and began working his way up the
local Democratic club. Just shaking every hand
he could. And some of that networking was purely
accidental. Our source highlights how Hyland
met John H. McCooey, who would eventually become
the immensely powerful Brooklyn Democratic Party
boss. Right. They didn't meet at a fancy political
gala. No, they met at the local post office.
McCooey was a postal clerk at the time, and Hyland
was just there sending money orders to his parents
to pay the interest on that new farm mortgage.
It's such a small world. McCooey showed him some
kindness regarding the paperwork. Hyland remembered
it, and they became lifelong friends. That is
a vital lesson for anyone navigating their own
career. Sometimes the most pivotal connections
happen during the most mundane errands. You never
know who the clerk across the counter is going
to become in 20 years. It's so true. All of this
local groundwork pays off when Highland emerges
from obscurity during the wild citywide elections
of 1903. This is where we get into the heavy
machinery of Tammany Hall politics. Oh, yeah.
The 1903 election was a chaotic internal power
struggle. For those who might need a refresher,
Tammany Hall was the formidable democratic political
machine that basically controlled New York politics
through a deeply entrenched system of patronage.
Meaning they handed out city jobs and contracts
to loyal supporters to maintain power. Exactly.
In Manhattan, Charles Francis Murphy had just
taken over as the head of the Tammany machine.
Murphy was a guy who got rich leasing city docks
to shipping companies, and his grand ambition
was to extend Tammany's influence out of Manhattan
and into all the outer boroughs. particularly
Brooklyn. To do this, Murphy decided to run George
B. McClellan Jr. for mayor, trying to dislodge
the current fusionist mayor. Right. And just
to clarify, a fusionist mayor was basically a
coalition candidate. Republicans and independent
Democrats teaming up specifically to keep the
Tammany Hall political machine out of power.
But the Brooklyn political leaders, headed by
a boss named Hugh McLaughlin, absolutely hated
Murphy's move. They felt McClellan would ruin
the down ticket raises in Brooklyn and cost them
local offices like the district attorney. You
saw right through it. Yeah. Many suspected Murphy
was doing this on purpose to cut off Brooklyn's
independent patronage base. It all came to a
head at the Democratic Convention on October
1st, 1903 at Carnegie Hall. It sounded like an
absolute madhouse. It was. Brooklyn Assistant
District Attorney Martin W. Littleton stood up,
looked directly at Murphy, and delivered a blistering
speech screaming about Tammany treachery. There
was wild applause, shouts of traitor, and massive
behind -the -scenes scheming to run an anti -Tammany
ticket. But Murphy just sat there, smiling through
the abuse, knowing he had the delegate math.
Tammany forced their slate through anyway. The
Brooklyn opposition collapsed, and in the resulting
turmoil, the old Brooklyn boss McLaughlin was
ousted by his own subordinate. This is the crucial
turning point for Highland. Instead of getting
swept away in the collapse of the old Brooklyn
guard, he aligned himself perfectly with the
new power structure. He knew which way the wind
was blowing. Because he had built such a solid
reputation among the working class and had those
connections with guys like McCooey, the new party
bosses saw him as a useful asset. In 1906, they
got him appointed as a city magistrate. Which
bridges a massive gap in his story. He didn't
just jump from a convention floor to the mayor's
office. He spent the next decade working as a
magistrate and later a county court judge, constantly
ruling in ways that favored his working class
base. He really used that time on the bench to
endear himself to powerful allies, particularly
the newspaper publisher William Randolph Hearst.
Hearst loved Hyland's anti -monopoly rhetoric.
He did. By 1917, Tammany Hall and Hearst needed
a reliable, populist candidate for mayor to take
back the city from reformers. Island was their
guy. He defeated the incumbent and won the mayoralty,
notably becoming the first Democratic candidate
to capture a significant portion of the African
-American vote. Once in office, he had a very
singular obsession for this way. Having been
a motorman himself, he understood that transit
costs disproportionately impacted the working
class. He was absolutely determined to keep it
strictly at five cents. To bypass the corporate
monopolies that ran the trains at the time, the
IRT and the BMT Highland set in motion the building
of the Independent Subway System, or the IND.
Right. It was designed to be entirely city -owned
and operated, competing directly with the private
lines to force them to keep fares low. That system
eventually became a massive chunk of the modern
New York City subway we know today. His fight
against the corporate monopolies wasn't quiet
either. In 1922, while sitting as mayor, he delivered
a highly publicized fiery speech attacking what
he called the invisible government. Yeah, that
speech is infamous. He described it as a giant
octopus sprawling its slimy legs over the nation.
He specifically called out the Rockefeller Standard
Oil interests and a small group of international
bankers claiming they control the majority of
newspapers, dictated who got nominated for public
office and virtually ran the U .S. government
for their own selfish purposes. And it's really
important to note for you listening that our
goal here isn't to endorse these 1920s conspiracy
theories. Absolutely not. We are. absolutely
not taking sides on his populist rhetoric or
saying he was right about this giant octopus.
Right. We are just looking at the historical
reality of how politicians of this era utilize
this kind of language to rally their base against
perceived elite control. Exactly. We are impartially
looking at the mechanics of his messaging. And
if we connect this to the bigger picture, the
mechanics of that messaging were rooted in very
deep -seated post -Gilded Age anxieties. The
wealth gap was staggering. The country had just
watched massive industrial concentration create
unprecedented wealth for a few, while heavily
impoverishing the working poor. Hyland, a man
who literally shoveled coal in a blizzard to
pay off a farm mortgage, was channeling the very
real anger of his constituents. But that constant
battling against the elites had a dark side for
his legacy. Despite his massive political power,
he was never respected by the intellectual or
political upper crust. They didn't consider him
highly intelligent or articulate. He was viewed
as a bit of a populist brute. His political opponents
actively worked to craft a narrative that he
was a buffoon. Because he wasn't a polished orator,
he was an easy target for the media and the political
operatives of the time, who delighted in mocking
him. Which brings us to one of the most painfully
funny anecdotes in the source material. According
to the legendary urban planner Robert Moses,
Hyland went through almost an entire mayoral
campaign using just one single stump speech,
his call, to keep the five -cent subway fare.
Just hammering that one point. Right. And he
eventually asked Moses to help him write a new
speech. Moses obliges and writes him a fresh
one. The first time Hyland tries to deliver it,
he reaches the dramatic climax. He's supposed
to invoke the Revolutionary War, a subject close
to his heart, given his grandfather's service.
Right. The line on the page is, I call for the
spirit of 1776. But Hyland completely misses
the historical context. He looks at the paper
and reads out the numbers individually, yelling
to the crowd, I call for the spirit. Spirit of
1776. Ouch. It's a devastating gaffe. And it's
exactly the kind of story that the elites circulated
to undermine his credibility. But it wasn't just
bad speeches that led to his downfall. By the
end of his second term, an investigative committee
appointed by Governor Al Smith severely criticized
his handling of the subway system. Wait, hold
on. If he was this champion of the working class
commuter, why was the governor's committee criticizing
his transit management? Was he actually mismanaging
it or was this just political sabotage from Al
Smith's camp? Well, it's a mix of both. His stubbornness
on the five cent fare meant the private transit
companies were starving for capital because they
couldn't raise fares to meet inflation. They
couldn't afford to maintain the lines or build
new ones fast enough to keep up with population
growth. So the system was falling apart. The
result was massive, dangerous overcrowding. Governor
Al Smith. who was also a Tammany Democrat but
aligned with a different faction, used this gridlock
as leverage to argue Hyland was ineffective.
So Tammany Hall, the very machine that helped
install him, turns on him. In 1925, they ran
the slick, highly charismatic state senator Jimmy
Walker against Hyland for the Democratic nomination.
And Hyland loses. But Red Mike still had one
last strategic hustle left in him. He realizes
he's out, but he strategically resigns from office
on December 30, 1925, exactly one day before
his term is officially supposed to end. Such
a classic move. Why? To assure his eligibility
for a $4 ,205 annual city pension. It was a purely
pragmatic, survivalist move from a guy who never
forgot what it felt like to have $3 .50 to his
name. Even in defeat, he secured his financial
future through a loophole. But Jimmy Walker couldn't
resist one final ultimate burn. After becoming
mayor, Walker actually appoints his defeated
rival, Hyland, to be a judge on the Queen's Children's
Court. When a journalist asked Walker why on
earth he would appoint his political rival to
a judgeship, Walker quipped, the children now
can be tried by their peer. It's a brilliant
cutting insult that highlights the absolute ruthlessness
of New York City politics. So what does this
all mean? We have a man who was endlessly mocked
by the political and media elites. They called
him a child. They laughed at his speeches. They
ousted him from power. And yet the same man initiated
massive infrastructure projects like the independent
subway system. He fiercely championed the working
poor against monopolies. He even had a mass.
14 -mile boulevard and Staten Island Highland
Boulevard named after him, despite his opponents
protesting it all the way. It really illustrates
the deep contradictions of a political legacy.
He wasn't polished, but he was effective at navigating
the brutal mechanics of the city. He understood
the needs of the people who rode the trains because
he used to drive them. It really is an incredible
journey. From a kid reading a borrowed book on
a mortgaged farm, shivering in the great blizzard
of 1888 laying tracks, to sitting in the mayor's
office at City Hall. He navigated the sharp elbows
of Tammany Hall, fought the corporate trusts,
and left a permanent physical mark on New York's
transit map. This raises an important question,
something for you to really mull over as we wrap
up today. Hyland spent his entire life fighting
the interests and the intellectual elites, fighting
fiercely for the working class. Yet, history
often remembers him through the jokes crafted
by those very elites like Jimmy Walker and Robert
Moses. Right. It makes you wonder, when we look
back at history, are we seeing the truth of what
a leader actually built, or are we just remembering
the punchlines written by the people who defeated
them? That is a phenomenal thought to end on
and a perfect lens through which to view the
stories we are told about historical figures.
Thank you so much for joining us on this deep
dive into the life of John Francis Hyland. We
hope you take that question with you and that
you keep exploring and questioning the history
around you. We'll see you next time.