Pap Singleton and the Great Exodus

0:00Finding great candidates to hire can be like, well, trying to find a needle in a haystack. Sure, you can post your job to some job board, but then all you can do is hope the right person comes along, which is why you should try Zippercrooter for free. At zippercrooter.com slash zip. Zippercrooter doesn't depend on candidates finding you. It finds them for you. It's powerful technology identifies people with the right experience and actively invites them to apply to your job. You get qualified candidates fast. So while other companies might deliver a lot of hay, Zippercrooter finds you what you're looking for. The needle in the haystack. See why four out of five employers who post a job on Zippercrooter get a quality candidate within the first day. Zippercrooter, the smartest way to hire. And right now, you can try Zippercrooter for free. That's right. Free. Zippercrooter.com slash zip. That zippercrooter.com slash zip zippercrooter.com slash zip. Welcome to today's deep dive.

1:01If 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 Pap 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, improving that true freedom is inextricably linked to economic independence. Okay. Let's unpack this. Where exactly does the story of Benjamin Singleton begin?

2:02Well, 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. 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,

3:04which just shows this early persistent refusal to accept his condition was not going to give up. No. Yeah. 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 one freedom during his time 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. 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, but he wasn't hoarding that money. He pulled those funds to operate a clandestine boarding house, helping other escaped slaves find their way to safety in Canada.

4:05That is incredible. It establishes the absolute template for his entire life, securing a baseline of personal stability, and then immediately turning around to build infrastructure to lift up his community. 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. When the 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 so. Well, the Civil War ends, the reconstruction era begins, but the grand political promises

5:07start to hollow out. Yeah, they really do. We've made men 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 a total sense. He realizes African Americans were never going to achieve parity in the post worst out 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 some recounting him. 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 National Area. Right. Keep it local. To execute this plan, they hit a massive systemic roadblock.

6:10Yeah. The white landowners in the area simply refused 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. They're 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 Singleton 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. Convince 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.

7:11A massive pivot. In 1875, Singleton begins exploring the idea of planting independent black colonies out West. He and Johnson traveled to Kansas in 1876. To Scotland, yeah. Right. In Cherokee County, which is situated in the southeastern corner of the state, he likes its rain, 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 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 macro economic problem. The year prior, rich lead deposits have been discovered in that exact area, 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 speculators paradise

8:14practically 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. So that's what it's like to live on the land and improve it for five years. So Singleton locates available, albeit marginal, land on the former Cauchy Indian reservation near the town of Dunlap, Kansas. OK. This area sits right on the borders of Morrison Lyon counties, conveniently situated along the tracks of the Katie Railroad. It provided the exact legal loophole they needed to bypass those hostile local markets

9:17and 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, 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. Starting from the Cumberland River Valley to a dugout in Kansas, I mean, that requires an astounding level of resilience. You really think? 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 Summary County areas

10:20to 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 Exodus. Exactly. By 1879, roughly 50,000 freedmen who became known as Exodus, 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 Exodus were heading in growth to states like Kansas, Missouri, Indiana, and Illinois, desperately seeking land, better working conditions, and just basic physical safety.

11:21Just almost migrating simultaneously. In Topeka, Kansas, the 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 Exodus 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. Also. Well, Singleton planned. The Exodus's fled. Right. When this massive influx of desperately poor, unresourced migrants arrived in Kansas, there were significant pushback. Many white Kansans began to aggressively object to their arrival. That in 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.

12:23He was fiercely defending their right to migrate and try to forge better lives in the America Vist. 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. Singleton stood his ground against the panel. He successfully rebuffed their efforts by pointing directly to his own success and 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 Friedman to leave their homes.

13:26In 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. 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. 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. 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

14:30they eventually planned to build a Friedman's Academy there. Recognizing that the colony's original independent structure had changed, Singleton stepped away from his direct dealings with Dunlap. So the Dunlap colony has handed over to a charity. And the initial wave of the great Exodus begins to slow down. You would think a man who is now 72 years old, who escaped slavery, ran a clandest in 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.

15:32Creating 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 brilliant. 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. In England, 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 were 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.

16:32Decades ahead of its time. Unfortunately, the momentum did not hold. After 1881, C. U.L. 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 1883, 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. 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 African movement.

17:32Exactly. The idea of global solidarity and returned to the African continent. He found the United Trans-Atlantic 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 Trans-Atlantic 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 whole mean? We look at this final era of his life from 1881 to 1889 when 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.

18:33How should we view this final stretch of his career? The value of these later years is not found in the material success or failure of those specific movements. Okay. This value lies in Singleton's unyielding imagination for liberation. That's a great way to put it. He absolutely refused to accept a ceiling on his people's potential. If the local real estate market in the South was rigged, he looked to the West. Right. If the West became too hostile or crowded, he looked to cooperative economics and cooling capital. When the entire domestic political system seemed entirely uncompromising, he looked to Cypress. 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 Pap Singleton's life is a brilliant study in the necessity of pivoting when a door slams in your face.

19:33Absolutely. Think about his trajectory. He looked 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 Lynx. 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 Maleficate 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

20:35family 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 Ellen's Worth, 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 for. 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 in Japan.

21:35It 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 are forced to abandon a failing plan, reinvent yourself, or step into the unknown, and might just be setting up your descendants for heights you can't even fathom.

22:37A 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. Finding great candidates to hire can be like, well, trying to find a needle in a haystack. Sure, you can post your job to some job board, but then all you can do is hope the right person comes along, which is why you should try Zippercrooter for free. At zippercrooter.com slash zip. Zippercrooter doesn't depend on candidates finding you, it finds them for you. It's powerful technology identifies people with the right experience, and actively invites them to apply to your job. You get qualified candidates fast, so while other companies might deliver a lot of hay, Zippercrooter finds you what you're looking for. The needle in the haystack. See why four out of five employers who post a job on Zippercrooter get a quality candidate within the first day. Zippercrooter, the smartest way to hire, and right now you can try Zippercrooter for free.

23:40That's right, free at zippercrooter.com slash zip. Finding great candidates to hire can be like, well, trying to find a needle in a haystack. Sure, you can post your job to some job board, but then all you can do is hope the right person comes along, which is why you should try Zippercrooter for free. At zippercrooter.com slash zip. Zippercrooter doesn't depend on candidates finding you, it finds them for you. It's powerful technology identifies people with the right experience, and actively invites them to apply to your job. You get qualified candidates fast, so while other companies might deliver a lot of hay, Zippercrooter finds you what you're looking for. The needle in the haystack. See why four out of five employers who post a job on Zippercrooter get a quality candidate within the first day. Zippercrooter, the smartest way to hire, and right now you can try Zippercrooter for free. That's right, free at zippercrooter.com slash zip.

24:44That zippercrooter.com slash zip zippercrooter.com slash zip.