Welcome to today's deep dive. If you're joining
us right now, you likely have that really intense
curiosity, that drive to truly understand the
mechanics of history. But... You know, you also
value your time. Right. Nobody wants to be buried
in raw data. Exactly. You want the thorough knowledge,
the deep insights, without feeling completely
overwhelmed. And today we're exploring an excerpted
Wikipedia article that covers the, frankly, extraordinary
life of Benjamin Papp Singleton. It really is
a phenomenal source. It details a story of just
sheer willpower and incredibly ambitious business
ventures. Plus, it shows a man who constantly
reinvented his approach to activism. He really
did. And our mission for this deep dive is to
explore how someone born into slavery, someone
who never had the opportunity to learn to read
or write, how he transformed himself into a visionary
leader of mass migration. It's a literal masterclass
in proving that true freedom is inextricably
linked to economic independence. OK, let's unpack
this. Where exactly does the story of Benjamin
Singleton begin? Well, it begins in 1809 in Davidson
County, Tennessee, which is right near Nashville.
Now, the historical record regarding his early
life is it's somewhat sparse. Which is pretty
common, right? Yeah, a very common reality for
individuals born into slavery. But we do have
a few foundational facts from the source that
set the stage for literally everything he accomplishes
later. Right. So he was the son of a white father
and an enslaved black mother. And from his youth,
there's this really poignant contradiction that
defines his daily life. Oh, the carpentry. Exactly.
He was trained as a skilled carpenter. So that
gives him a highly valuable, tangible trade.
I mean, he could build things with his own hands.
Which is huge. It is. But alongside that mastery,
he carried a lifelong, really heavy regret over
the fact that he was never taught to read or
write. Carrying that burden while possessing
such a brilliant strategic mind. It's just a
fascinating tension. Yeah. And the historical
accounts note he made several unsuccessful attempts
to escape slavery, which just shows this early,
persistent refusal to accept his condition. Who
was not going to give up. No. And finally, in
1846, he makes a successful break. He navigates
the Underground Railroad, traveling north and
crossing all the way into Windsor, Ontario. Right
across the border. Right. But after spending
about a year in Canada, he makes this interesting
geographic pivot. He moves back into the United
States to settle in Detroit, Michigan. And what's
fascinating here is how Singleton utilized that
hard won freedom during his time in Detroit.
Yeah. Tell us about that. He did not simply cross
the border, secure his personal safety and just,
you know, quietly fade into a comfortable life.
Right. He actually lived as a scavenger and worked
as a carpenter. He was literally picking through
the streets and utilizing his woodworking skills
just to scrape together meager resources. Just
to survive. But he wasn't hoarding that money.
He pooled those funds to operate a clan. Wow.
That is incredible. So he's using his trade to
survive, but his street smarts to navigate others
through that final, really dangerous stretch
to safety. Exactly. And he remains in Detroit
until the Civil War is well underway. Then, in
1862, the Union Army occupies Middle Tennessee,
and Singleton makes the decision to return to
Nashville. He heads back, believing his freedom
will be protected within those union lines. Right,
right. Taking up residence in Nashville, he returns
to his trade. He starts working as a cabinet
and coffin maker. Coffin making. Yeah. It was
a stark, grim reality of the era, given the war,
but it was a very steady economic anchor for
him. I can imagine. And during this period, this
extends from 1862 through 1875, Singleton undergoes
a really profound paradigm shift. I saw. Well,
the Civil War ends, the Reconstruction era begins,
but the grand political promises start to hollow
out. Yeah, they really do. Freedmen were facing
severe political marginalization and pervasive
racial violence. And Singleton observes this
landscape. He concludes that legal freedom is
essentially meaningless without financial autonomy.
That makes total sense. He realizes African -Americans
were never going to achieve parity in the post
-war South without controlling their own capital.
And that realization leads him to take matters
into his own hands rather than just, you know.
Waiting on political leaders who are actively
failing to deliver equality. Exactly. He stops
waiting. So in 1869, he forms an alliance with
Columbus M. Johnson. A black minister in Sumner
County. Right. And they start looking for highly
practical ways to establish economic independence.
By 1874, they take their first major swing. They
found the Edgefield Real Estate Association.
A huge step. And the goal is incredibly straightforward.
Just help African -Americans acquire land. Right
there in the Nashville area. Right. Keep it local.
But when they attempt to execute this plan, they
hit a massive systemic roadblock. Yeah, the white
landowners in the area simply refused to bargain
with them. Refused entirely. The historical record
shows these landowners formed a sort of localized
blockade. They demanded exorbitant, artificially
high prices for their property. And this was
done to intentionally price Singleton's group
right out of the market. Just completely shutting
them out. Yeah. It was a clear refusal to allow
Friedman to participate fairly in the local economy.
Singleton and Johnson had the organizational
structure. They had the community buy -in. Exactly.
But they were facing... a rigged market. And
Simleton understands that if the local real estate
system is structurally designed to keep them
out, they cannot stay and play a losing game.
You can't win if the rules are rigged against
you. Right. Convinced that Friedman absolutely
had to leave the South to achieve any sort of
real economic independence, he actually renames
his group the Edgefield Real Estate and Homestead
Association. Here's where it gets really interesting.
If they couldn't buy land in the South, they
were going to look to the American West. A massive
pivot. In 1875, Singleton begins exploring the
idea of planting independent black colonies out
west. He and Johnson travel to Kansas in 1876.
To Scoutland, yeah. Right, in Cherokee County,
which is situated in the southeastern corner
of the state. He likes the terrain, heads back
to Nashville, and starts aggressively recruiting.
And that scouting trip culminates in their first
major attempt at a colony in the summer of 1877.
The Baxter Springs attempt. Exactly. Singleton
leads a group of about 73 settlers to Cherokee
County near a town called Baxter Springs. They
begin negotiating with the Missouri River, Fort
Scott and Gulf Railroad for land to build their
settlement. There's a problem. A massive macroeconomic
problem. The year prior, rich lead deposits had
been discovered in that exact area. Oh, wow.
Triggering a huge mining boom. It is the ultimate
nightmare scenario for anyone trying to buy real
estate. You know, a localized resource rush turns
cheap, available land into a speculator's paradise
practically overnight. Overnight? Just like back
in Nashville. Land prices skyrocket completely
out of their reach. Their pooled funds simply
aren't enough to compete with mining speculators.
So without the ability to secure the land, the
Baxter Springs colony fails before it can truly
begin. It's devastating. It is. But Singleton's
response to failure is always a pivot. Always.
He stops looking at commercial railroad land
and shifts his focus to government land. specifically
looking to utilize the 1862 Homestead Act. And
the Homestead Act was a crucial piece of legislation.
It allowed individuals to claim 160 acres of
government land for just a small filing fee.
A huge opportunity. Right, provided they lived
on the land and improved it for five years. So
Singleton locates available, albeit marginal,
land on the former Kaw Indian Reservation near
the town of Dunlap, Kansas. Okay. This area sits
right on the borders of Morris and Lyon counties,
conveniently situated along the tracks of the
Katy Railroad. It provided the exact legal loophole
they needed to bypass those hostile local markets
and the speculative pricing. And the imagery
of this specific migration is just incredibly
vivid. In the spring of 1878, Singleton settlers
leave Middle Tennessee. They travel via steamboats
on the Cumberland River. Quite a journey. Leaving
the lush, familiar southern landscapes for the
stark reality of the Great Plains. And the records
detail that their first year was incredibly harsh.
Extremely harsh. Most of these settlers survived
by living in dugouts. They were literally carving
their initial homes right out of the earth just
to survive the winds and the winter elements.
Moving from the Cumberland River Valley to a
dugout in Kansas, I mean, that requires an astounding
level of resilience. It really does. They were
battling the elements, the isolation, and just
the sheer physical toll of breaking untouched
prairie soil. But they do it. They do. They stick
it out. They established the Dunlap Colony, officially
organizing it in 1879, and it turns into a massive
success. Yeah. Ultimately, over 2 ,400 settlers
emigrate from the Nashville and Sumner County
areas to this specific settlement. Seeing 2 ,400
people successfully relocate and build a self
-sustaining community, that's a monumental achievement.
It is. But 1879 is also the year the entire landscape
of Western migration shifts dramatically. It
marks the beginning of what becomes known as
the Great Exodus. Right. Because while Singleton
was meticulously planning and organizing his
specific Dunlap colony, a much larger, entirely
organic movement was taking shape across the
South. The Exodusters. Exactly. By 1879, roughly
50 ,000 freedmen who became known as Exodusters
began a massive, uncoordinated migration out
of the former Confederacy. 50 ,000. That is a
staggering scale. It really is. And they were
fleeing, crushing. poverty and a severe resurgence
of racial violence as whites regained political
control in the South. These exodusters were heading
in droves to states like Kansas, Missouri, Indiana
and Illinois, desperately seeking land, better
working conditions and just basic physical safety.
almost migrating simultaneously. In Topeka, Kansas,
they even formed a community that became known
as Tennessee Town due to the sheer volume of
migrants arriving from that specific state. Yeah,
the numbers were overwhelming. And most of these
exodusters had absolutely no direct connection
to Singleton's carefully planned colony movement.
They were simply fleeing. If we connect this
to the bigger picture, you see Singleton's true
character emerge during this crisis. How so?
Well, Singleton planned. The exodusters fled.
When this massive influx of desperately poor,
unresourced migrants arrived in Kansas, there
was significant pushback. Many white Kansans
began to aggressively object to their arrival.
That economic strain, I imagine. Economic strain,
social upheaval. And Singleton could have easily
distanced himself. He could have pointed to his
successful Dunlap colony and separated his organized
settlers from the chaotic mass migration. Kept
his head down. Exactly. But instead, he stepped
forward. He became their nationally recognized
spokesman. He was fiercely defending their right
to migrate and try to forge better lives in the
American West. He steps directly into the spotlight
to become the face of the movement. He does.
And this visibility leads to a highly dramatic
moment in 1880 when Singleton is requested to
appear before the United States Senate in Washington,
D .C. The Senate hearings? Yeah. He's called
to testify on the underlying causes of this great
exodus to Kansas. And the transcripts from those
Senate hearings reveal a very tense, highly partisan
affair. What happened? Southern senators actively
attempted to discredit the Exodus movement. They
were questioning the motives of the migrants
and trying to downplay the severity of the conditions
in the South. Denying the reality. Yeah. But
Singleton stood his ground against the panel.
He successfully rebuffed their efforts by pointing
directly to his own success in setting up independent,
functioning black colonies. He had the proof.
He did. And he clearly, systematically laid out
the terrible conditions, the violence and the
economic suppression that were actively forcing
freedmen to leave their homes. In his testimony
notes, there's a quote that is absolutely heartbreaking,
yet it captures his entire driving force. Oh,
I know the one. He stated, I have been a slave,
fled to Canada when my children were small, and
19 years after when I returned, they were grown.
It is a devastating summary of exactly what the
institution of slavery stole from him. 19 irreplaceable
years of his children's lives. Yeah. And he used
that profound loss as fuel to ensure others wouldn't
have their futures dictated by the same oppressive
system. That was powerful. It is. On a practical
level, however, this massive wave of migration
did have severe consequences for his work in
Kansas. Right. The strain on Dunlap. Exactly.
The sheer volume. of desperately poor arrivals
put a massive financial strain on the Dunlap
colony. It far exceeded what the original, self
-sustaining settlers could handle. It was just
too much. By 1880, the situation required outside
intervention. A Presbyterian church charity had
to take control of the settlement to provide
aid, and they eventually planned to build a freedman's
academy there. Okay. Recognizing that the colony's
original independent structure had changed, Singleton
stepped away from his direct dealings with Dunlap.
So the Dunlap colony is handed... over to a charity,
and the initial wave of the great exodus begins
to slow down. Right. You would think a man who
is now 72 years old, who escaped slavery, ran
a clandestine boarding house, built coffins and
moved thousands of people across the country
would finally rest. You really would think that.
During 1881, most people are affectionately calling
him Old Pap. But his focus merely shifts from
geography to pure economics. He just keeps going.
He starts a brand new organization right there
in Topeka called the Colored United Links. or
the cul his drive to find a solution is just
relentless the core concept behind the cul was
economic pooling like what he did in detroit
very similar but on a larger scale he wanted
to combine the financial resources of black people
across the region to build black owned businesses
factories and trade schools creating a whole
ecosystem exactly the idea was to create an internal
self -sustaining economy a cooperative economic
blueprint where the community controlled its
own supply chains and capital that's And the
group actually held several conventions. They
gained enough local traction that Republican
Party officials in Kansas started eyeing their
political strength. They were making waves. Singleton
even held meetings with James B. Weaver. The
presidential candidate for the Greenback Party.
The Greenback Party. Yeah. At the time, they
were an anti -monopoly political faction. They
advocated for an unbacked fiat currency, which
strongly appealed to working class folks and
farmers who are being completely crushed by the
mainstream financial system and the gold standard.
Right. They actually discussed a potential fusion
between their groups to amplify their political
and economic leverage. The ambition there to
link a localized cooperative. economic movement
with a national anti -monopoly political party
is incredibly forward -thinking. Decades ahead
of its time. Unfortunately, the momentum did
not hold. After 1881, CUL membership faltered.
And the organization eventually dissolved. And
this particular failure seems to trigger a massive
shift in his perspective. He becomes convinced
that African -Americans will never be allowed
to truly succeed or integrate within the existing
power structures of the United States. Right.
He hits his limit. He pivots away from domestic
strategies entirely and shifts his focus to global
ambitions. The strategies become increasingly
radical as his frustration with the American
system grows. Tell us about Cyprus. Yeah. In
1880. he teams up with a businessman from St.
Louis and a black minister to propose a migration
of American blacks to the Mediterranean island
of Cyprus. Wow. Cyprus. It was a very bold geographical
leap, though the idea never really gained practical
traction. But he doesn't stop there. No. Two
years later, in 1885, he moves to Kansas City
and turns his focus toward Pan -Africanism. The
Back to Africa movement. Exactly. The idea of
global solidarity and return to the African continent.
He founds the United Transatlantic Society, or
UTS, advocating for all blacks to relocate to
colonies like Sierra Leone and Liberia. And the
UTS manages to last until 1887. but never actually
succeeds in sending anyone to Africa. The logistics
and funding required for transatlantic migration
were simply too steep. It was a monumental task.
It was. Finally, in 1889, in poor health and
mostly retired from daily activism, he raises
his voice one last time. The Oklahoma proposal.
Yeah. He calls for a portion of the newly opening
Oklahoma territory to be reserved strictly as
an all -black state, completely separate from
white governance. He was trying everything. So
what does this all mean? We look at this final
era of his life from 1881 to 1889 and we see
a string of ventures. The COL, the Cypress proposal,
the Back to Africa UTS, the Oklahoma statehood
idea. Right. On paper, these all ultimately fail.
How should we view this final stretch of his
career? That's a great way to put it. Right.
seemed entirely uncompromising. He looked to
Cyprus. He looked to Africa. He looked to carving
out a brand new territory entirely. He possessed
a relentless flexibility. He never stopped trying
to engineer a way out of oppression, constantly
theorizing new blueprints for autonomy when the
old ones were blocked. And that relentless flexibility
is exactly why this history is so deeply relevant
to you today. Benjamin Pabst Singleton's life
is a brilliant study in the necessity of pivoting
when a door slams in your face. Absolutely. Think
about his trajectory. Blocked by landowners in
Nashville, priced out by a lead mining boom in
Baxter Springs, he immediately finds a legal
loophole with the Homestead Act in Dunlap. He
never got stuck. Never. He demonstrates the immense
power of pooling resources, starting from his
days as a scavenger in Detroit all the way to
his vision for the colored United Links. Most
importantly, his life underscores the realization
that true autonomy often requires the exhausting
work of creating your own spaces entirely. rather
than just asking for a seat at a table where
the game is already rigged against you. His legacy
is undeniably profound. He passed away on February
17, 1900, in Kansas City, Missouri. Over a century
later, in 2002, the scholar Maleficent Asante
rightfully included Pap Singleton in his biographical
list of the 100 Greatest African Americans. Well
deserved. The structural impact he had on Western
migration is cemented in history. But the most
striking and personal part of his legacy is actually
found by tracing his family line. This is my
favorite part of the source material. Yeah, the
excerpt provides this incredible, almost cinematic
glimpse into his descendants. We know his son,
Joshua W. Singleton, eventually settled in Ellensworth,
California. Which itself was an independent black
agricultural settlement. Right. The instinct
to seek out independent spaces clearly passed
down. But the story takes a fascinating turn
in The Next Generation. Joshua's grandchildren,
who are Benjamin Singleton's great -grandchildren,
were John Jr., Midge, Charles, and Robert Williams.
The Williams family. As young adults, they formed
a vocal group. Initially, they performed as the
Williams Quartet in the Bay Area, and by 1928,
they were touring widely as the Williams Four.
Wow. Midge Williams also broke out as a highly
successful swing jazz soloist. By 1933, this
group The direct descendants of a man who escaped
slavery on foot and lived in a dugout on the
plains were successfully touring the globe. It's
unbelievable. Performing in places as far away
as Shanghai and Japan. It is a stunning trajectory
over just two generations. A man who carried
the heavy regret of never learning to read. who
spent his entire life trying to carve out just
a few safe acres of land for his community set
a powerful precedent of geographic mobility and
fearless exploration. A huge precedent. And that
precedent resulted in his grandchildren crossing
oceans to become international jazz stars. This
raises an important question. How does the bravery
of taking one single localized step toward freedom
today echo across the globe generations later?
Singleton couldn't possibly imagine his grandchildren
singing in Shanghai, but his willingness to walk
away from bondage, to build a life from scratch,
to sit before the U .S. Senate and demand recognition.
it fundamentally broke a generational chain.
It changed their entire trajectory. It leaves
you to mull over how your own difficult pivots,
the times you were forced to abandon a failing
plan, reinvent yourself, or step into the unknown,
might just be setting up your descendants for
heights you can't even fathom. A powerful reminder
that our pivots reverberate far beyond our own
lifetimes. Thank you for taking this journey
with us today. Keep asking those big questions.
Keep looking for those surprising connections.
And as always, keep diving deep.