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Stuff You Should Know: The Pinkerton Detective Agency
Episode Summary In this episode of Stuff You Should Know, hosts Josh and Chuck delve into the history of the Pinkerton Detective Agency, one of the most renowned and controversial detective firms in U.S. history. The discussion covers the agency's founding by Alan Pinkerton, its early contributions to social causes, and the significant shifts in its reputation over time, particularly its role in labor disputes and union busting.
Key Points
Origins of the Pinkerton Detective Agency
- Founding: Alan Pinkerton founded the Pinkerton National Detective Agency in 1850 after emigrating from Scotland.
- Early Work:
- Involved in the abolitionist movement, helping enslaved people escape via the Underground Railroad.
- Gained a reputation for capturing criminals and worked initially with railroads to prevent theft.
Notable Incidents
- Lincoln's Assassination Plot:
- Pinkerton thwarted an assassination attempt on Abraham Lincoln before his inauguration, leading to significant recognition.
- He utilized disguises and employed the first female detective, Kate Warren, to aid in Lincoln’s safe passage.
Innovations in Detective Work
- Adoption of New Techniques:
- Introduced practices such as mugshots, fingerprints, and criminal databases, laying groundwork for modern law enforcement.
Role in the Civil War
- Military Intelligence:
- Pinkerton served as a head spy for the Union Army but faced criticism for inaccurate intelligence assessments that prolonged the war.
Reputation Shift
- Union Busting:
- By the late 19th century, the agency shifted focus towards infiltrating and dismantling labor unions, notably during the Homestead Strike, which resulted in significant violence and public backlash.
- Molly Maguires:
- The agency played a key role in the prosecution and execution of members of the Molly Maguires, a secret society of Irish miners, leading to ethical controversies.
Controversial Legacy
- Labor Relations:
- The Pinkertons became synonymous with corporate oppression of labor movements, leading to a tarnished reputation that persists today.
- Congressional Investigations:
- The agency’s actions during labor disputes prompted investigations and increased scrutiny from lawmakers.
Modern Day
- Acquisition:
- In 1999, the Pinkerton brand was acquired by Securitas, but it continues to operate under its historical name, providing corporate security services today.
Key Takeaways
- The Pinkerton Detective Agency's history is marked by a dual legacy of pioneering detective work and contentious labor relations.
- Alan Pinkerton's early humanitarian efforts were overshadowed by the agency's later alignment with corporate interests.
- The agency’s controversial methods during labor strikes transformed public perception and led to significant legal scrutiny, shaping modern labor relations in the U.S.
Concluding Remarks The Pinkerton Detective Agency serves as a fascinating case study of how organizations can shift from noble beginnings to notorious reputations through their actions and alignments. The episode emphasizes the complexity of their legacy, raising questions about ethics in law enforcement and corporate influence on society.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
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1:01John Polk story on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Welcome to Stuff You Should Know, a production of iHeartRadio.
1:20Hey, and welcome to the podcast. I'm Josh, and there's Chuck, and there's Jerry, and this is Stuff You Should Know, and we're keeping an eye on you, sucker. Did I throw you off when I pre-recording? No, I'm always expecting anything from you. We do our usual countdown, everyone, so we can sync sound. And you do that. Here's a little how the sausage is made. You do that by counting down and then each of us clapping. So you have a spike in the audio wave file that the engineers and editors can align. So we match up. Right. And I clapped. But this time I also said, Schlemiel! Hoping you would say Oh, you set me up, huh?
2:02I'm sorry That's okay Well, here, let me say it now Schlemazel There you go Okay, are you ready to get on with our sausage party? Gross Yeah, sure Okay That was nice of you to kind of give that behind-the-scenes tour to everybody, Chuck You know That's why everyone likes you more Trade secrets, that's not true I've been on Reddit Whatever Everybody likes you, including me, especially me. At any rate, so we're talking today about the Pinkerton Detective Agency. And this one strikes me as odd that we have waited this long, 17 years to finally talk about them. Yeah. And because they're just so legendary, you know, like everybody knows what the Pinkertons are.
2:47And if you don't, I'm not taking that back because everyone else knows what the Pinkertons are. Yeah. The Pinkerton National Detective Agency technically was the name of it, but they were generally called the Pinkertons led by Alan Pinkerton. And they're, you know, what they're known for is being one of the first or perhaps the first. And I say private detective agency, but not like we think of PIs like. Not Sam Spade stuff. No, no, no. Just a detective agency that's privatized, like police kind of detective work. Right. And, you know, they did a lot of stuff, including, as we'll see, busting up bank robbers and then later busting up unions.
3:29Yeah, it took a dark turn for sure. Yeah, but they got their start doing, you know, God's work by working in the abolitionist movement, by helping to free enslaved people. Yeah, yeah, that's one thing. So there's a lot of stuff you'll find when you dig into the history of the Pinkerton Detective Agency. it depends on who you're reading. Either they were pretty great and did some really great work or they were evil from the start. And then apparently also one of the things that complicates it is Alan Pinkerton was known to kind of hype his own company, hype his own exploits. And some people interpret that as like personal myth-making.
4:12And whether that's correct or not, a lot of historians have delved into And I think the answer generally is it's a case-by-case thing, whether it's actually true, whether it actually happened quite that way. But for the most part, from what I saw from researching this is generally most of the stuff can be accepted at surface level for the most part. It's not like if you buy into this story that we're about to tell you that you're just being totally misled. So for the most part, just relax is what I'm trying to say. Yeah, so we'll go back in time and hop in the Wayback Machine to witness the birth.
4:55It's 1819 in Scotland, so it's not a pretty sight. No. Giving birth back then, but little Alan Pinkerton is born in Scotland. He is the son of a police sergeant, so, you know, law enforcement was in his family roots. And he went to the United States in 1842 at the age of 23. And we should kind of mention just one thing he was involved in early on in Scotland before he left was something called the Chartist Movement, which was we're not going to get super into it. But it was basically a movement of the working class over there that tried one of the main things they tried to do is extend voting rights to all men, non-landowners, that is.
5:38Right. Yeah. Yeah, and election of parliamentary members, that kind of stuff. It's basically democratic reform in England. And at the time, this was considered radical politics. Yeah. And Alan Pinkerton actually fled the country with his family because the fuzz was looking for him, essentially. And they landed in the Chicago area, Dundee, Illinois, appropriately enough. Yeah. And he decided that he would become a cooper. Yeah. Which is somebody who makes barrels. And I guess he was a pretty decent barrel maker because he did it for a little while. Yeah, it's a trade he learned in Scotland. So he opened up that cooperage in Dundee, like you said.
6:17And a fortuitous incident happened as a cooper when he was on apparently this sort of abandoned or maybe just not claimed land, cutting wood, looking for wood for barrels. And he discovered a hideout of some counterfeiters. He rustled up a posse, got some citizens together and captured them. And for his efforts, got a lot of local notoriety. And they said, hey, how about you become deputy sheriff here in Kane County, Illinois? And this was in 1846. And he said, well, I guess dad was a was a copper. And so maybe I should be, too, or a quasi copper, at least. Yeah, this was actually before Chicago had an established police force.
7:00And it was a big deal to be a cop. And if you were a cop, they also called them watchmen because in a lot of cases, that's what it amounted to. Like these men would not go into the highest crime areas and they would avoid the most dangerous criminals. And there were just a few handfuls of them. But Pinkerton made a name for himself very quickly as somebody who had just like a sixth sense for just knowing when somebody was up to no good and following them and seeing what they were up to. for being fearless and for not accepting bribes. He was as honest as the day is long as far as bribery is concerned, and that made him stand out, and he started kind of moving up the ranks pretty quickly and moved from Kane County to Cook County where he worked in the assessor's office protecting Steven Spielberg.
7:55Well, I'm not sure I get the reference. From Blues Brothers. Remember, wasn't Steven Spielberg the Cook County assessor eating the sandwich when they come to pay the taxes? Frank Oz? No, Frank Oz was the guy in the property room. Oh, was Spielberg in that too? Okay. I'm pretty sure he was the assessor at the Cook County assessor's office. I believe you. I just, I don't, I shamefully don't know Blues Brothers as well as clearly you do. So either I'm like really just making this stuff up, but we've had this conversation. And we were fully on board with Spielberg being the assessor. Oh, you know me.
8:33And I mean, this was like two weeks ago. No, it wasn't. OK, it wasn't two weeks ago, but we have had this conversation. I know we have. I've just turned 54, so things are slipping. All right, I'll ease off. Yeah, so that's what happened. Eventually, he would also be a special agent for the U.S. Post Office. And finally, in 1850, he started the detective agency, the Pinkerton National Detective Agency. Apparently, he was named the first detective in Chicago, I think, previous to this, at just 31 years old. And from the beginning, from 1850 until the end of emancipation, like I mentioned from the outset, he worked to assist the escape and freeing of enslaved people.
9:18I think he even had to volunteer to stop on the Underground Railroad. Yeah, so there was one. He apparently was bosom friends with John Brown, as he put it. He had a real chance to coin the term bosom buddies, but he didn't do it. Bosom friends. Yeah. Doesn't have the ring, does it? No, it really doesn't. But John Brown, the white abolitionist guerrilla, essentially, made a raid on a few farms in Missouri and ended up freeing 11 enslaved people and leading them to Canada. And one of the stops was with Alan Pinkerton in Chicago. And Pinkerton by this time was wealthy enough that he paid for, I guess, the train ride from Chicago on to Detroit for everybody who John Brown had busted out.
10:05So he definitely was an abolitionist. And from what I read, it was like from the moment he landed in the United States, he was an abolitionist. This wasn't like him pumping up his image years later. Yeah, yeah, for sure. So a lot of the other work they were doing, they were doing other work as an agency besides working in the emancipator, I guess, the abolitionist movement. But this was, you know, again, in and around Chicago that didn't have a real police department at the time. And he they didn't exactly work as cops, though. It was sort of this weird hybrid of a thing. Like they were it wasn't like police.
10:45It wasn't like a private detective agency, but they also weren't like full on cops. It was kind of hard to define at the time. Yeah, I think one of the big distinction was they weren't out there like actively seeking crime as part of the public good. They were hired to find like specific things, specific criminals or to prevent specific crimes by corporations typically. And one of the early employers or clients, I guess, were the railroads, because at the time people would steal from railroads left and right. There were just so many goods going across the United States. It was just too tempting.
11:22And they started, I think, the first railroad, possibly, if not one of the first, was the Illinois Central Railroad. And they worked security and did detective work for this railroad. And this would be a significant client for Pinkerton to land throughout the rest of his life because the corporate attorney for the Illinois Central Railroad at the time was Abraham Lincoln. And the president of the railroad was William McClellan. And when you put those two together, you have some high-powered Civil War people on the Union side. And as we'll see, Alan Pinkerton joined them in the Civil War. Yeah.
12:00If you've ever seen, there weren't a lot of photographs back then, but there's a very famous photograph of Lincoln at Antietam. Have you ever seen this one? Yeah, I was looking at it today. Yeah. So that's Pinkerton on the left. He's with two dudes standing in front of that canvas tent. And that's Pinkerton on the left and Major General John McLernan on the right of Lincoln, who I always just not forget. But anytime you see a photo like that where you and there aren't many where you see like full size, the full size Lincoln doll. Right. Yeah. Or cardboard cut out. He's just impossibly tall for back then.
12:35And then that stovepipe hat just adds to it, obviously. But I don't know if he wore that hat to further intimidate people. But he was just such a tall, lanky guy. It's just odd looking for that time period. For sure. I have trouble any time I say stovepipe hat, not saying stovetop hat. Instead of potatoes? That was raised on stovetop stuffing. Did you eat that stuff? Yeah. Ah, we never got to eat that stuff. My mom didn't buy that stuff. Yeah, we ate that stuff for sure. We ate all sorts of weird stuff like that. Isn't it just like dehydrated bread crumbs? Yes, but very tasty and savory. With herbs and stuff?
13:14Mm-hmm. And what do you do? You just mix it with some, or put it on a casserole topper? You put it in a pot with some, wait, you boil a little water. and then you add it to the water, soaks up the water, and then you add like 10 sticks of butter, which is really what drives the whole thing home. There you go. And then, yeah, you put it in your mouth directly from the pot, typically. All right. Well, this episode is clearly brought to you by Stovetop Stuffing instead of potatoes. Hey, one other thing too, while we're on a tangent, I mentioned Sam Spade earlier. I cannot recommend enough the limited series Monsieur Spade.
13:50I think it's on Netflix. Starring Clive Owen. Have you seen it? I have not. Oh, my God. It's so good. But at the same time, I've never seen such a tightly constructed show just come totally off the rails in like the last hour. In a bad way? Yeah. I mean, ultimately, compared to the rest of the show, it's bad. But it's almost like they forgot that they had to wrap it up and they just shot a scene. And that was it. And it was like so totally improbable and just stood out so far from the rest of the series that you're just like, what? But luckily the rest of the series is so great it doesn't really damage it at all.
14:33Well, you led me down the right path with Black Dove, so I'll give it a shot. I'm really glad you guys liked that. Did you finish it? Yeah. Yeah, that's good. That one fell apart at the end too. You think? Mm-hmm. Huh. I liked it. Maybe you just don't like things ending. Yeah. I hadn't thought about that. Maybe not. All right. Back to who we're talking about here, Pinkerton, not stovepipe or stuffing. So, like I said, he was or like you said, I guess he was buddies with Lincoln pre-Civil War and had gotten to know, what was his name? William McClellan, who would become the general. That's right.
15:14The head of the Union forces. That's right. So that leads us to a story, a pretty major story early on. I guess it's not that early on. It's about 11 years into the detective agency. But Pinkerton learned of a assassination plot against president elect Lincoln at the time. And there was a barber in Baltimore from Corsica. His name was Cipriano Farandini. And he wanted to kill Abraham Lincoln when he was coming through Baltimore, when Lincoln was on his way to Washington. and Pinkerton, you know, found out about this and was like, you're not going to kill my buddy. I'm going to thwart your plan.
15:54Yeah, he did. This was apparently like part of a general plan to prevent Lincoln from making it to his inauguration in Washington. Right. Just kill him in Baltimore. Problem solved. Right. So as Lincoln got toward Baltimore, they they enacted a plan where he was He was taken off of the train at a stop, I think, like Harrisburg or something right before Baltimore. And he was disguised. And he basically played the brother of a woman named Kate Warren, who is a detective who we'll talk about in a second. And she escorted him on another train through Baltimore that went through at night. Again, in disguise.
16:37No one knew who he was. And one of the things that kind of came out of the story that was so significant was that Kate Warren stayed up all night and watched over Abraham Lincoln on this train ride to Washington, D.C. And that kind of coined this term or this slogan that they adopted, we never sleep, and led to the logo, which was this open eye, like the all-seeing eye that's watching you that never sleeps. And that eventually led to just the term private eyes, right? Yes. Yeah, I imagine Lincoln was a pretty hard guy to disguise now that I think about his height, that mustache-less beard, and that hat.
17:17Like, they're probably like, take off the hat to begin with. They did. First things first, get that hat off your head. Right. Get that stovetop hat off your head. And they got a Sharpie. They drew on a mustache. And then they probably put him, if they would have been smart, they would have put him like in a wheelchair or something. Which they may have done. As a matter of fact, I saw that he was, I guess the term that you would use today is like he posed as a handicapped brother to Kate Warren. Oh, there you go. Oh, and told him to lower his voice. Right. He's a very good amateur. It was very shocking still when everyone saw Lincoln and Daniel Day-Lewis came out like this.
17:56Yeah, I know. I know. It was quite a choice. And only Daniel Day-Lewis would have been allowed to do that, too. Yeah, totally. Anybody else, the director, would have been like, what are you doing? Yeah, exactly. You don't question him. So you mentioned Kate Warren. Is it Warren and not Warnie? I think it's Warren. Okay. W-A-R-N-E. She's very notable, too, though, aside from just assisting in this plot to save Lincoln, or I guess action to save Lincoln against the plot. But she was a detective like Pinkerton in a very forward thinking sort of way in 1856 hired her after she convinced him like, hey, you got, you know, there are things that women can do, places we can infiltrate information we can get in ways that men cannot.
18:42And he saw the value in that, hired her, and then I think but four years later made her head of the Female Detective Bureau. So they kind of staffed up with some women to work in these undercover roles. Yeah, and it's really like this was unheard of. So 1856 is when he hires her. The first actual sworn policewoman that I could find in the United States was a woman named Lola Baldwin in Portland, Oregon. Yeah, in 1908. Okay. So 44 plus 8 is 52 years. Yeah, 52 years. ahead of schedule. That's great. Pinkerton hired a woman and made her a very famous detective. And just super smart, you know, because she was right on the money.
19:28I'm sure they were great assets to their cause. For sure. You want to take a break? Yeah, let's do it. Okay.
19:51New year, new goals, and in this economy, a better money plan is more necessary than ever. I am Matt. And I'm Joel. We are from the How to Money podcast, and every week we help you to spend smarter, save more, and make sense of what's going on out there. If you want 2026 to be the year you finally feel in control of your money, we're here to give you the tools and advice to help you make it happen. Listen to How to Money on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hi, I'm Dr. Priyanka Wally. And I'm Hari Kondabolu. It's a new year. And on the podcast Health Stuff, we're resetting the way we talk about our health.
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22:29All right. So we're back with more on Pinkerton. The Civil War would begin. And Lincoln put George McClellan, who we've previously mentioned as someone who knew Pinkerton through the railroad business, put him in charge of the Army of the Potomac. And he said, hey, Pinkerton does pretty good work. I'm going to bring this guy in as sort of a head spy. We'll call it like a secret service division. And he worked under, Alan Pinkerton, that is, worked under the codename Major E.J. Allen and was pretty good at rooting out spies, but not so good at intelligence gathering and interpretation. No, he rooted out a spy ring led by a woman named Rose O 'Neill Greenhow, who was a Southerner but was still like the toast of Washington, D.C.
23:16society. And she was really running a very sophisticated and very developed spy ring for the Confederacy. And he found her out, busted everybody. It was a big deal. But with estimating troop strength, no. He may have single-handedly added years onto the Civil War when he told McClellan, General McClellan, that he estimated the Confederates had between, I think, 100 or 200 ,000 troops. Yeah, I saw 200. Yeah. So at the time, Robert E. Lee had 40 ,000 to 45 ,000 troops. So he grossly overestimated it. And McClellan had something like 76 ,000 troops. So they could have very easily overwhelmed the Confederacy early on.
24:06Yeah. Had Pinkerton not overestimated the troops and had – I also saw McClellan didn't vet that information at all. He just took it on face. And by the way, all of you Civil War buffs, if you can go back and unsend your emails, it's not William McClellan. It's George B. McClellan. I'm sorry. I misspoke. Oh. I think I said William too, didn't I? Or did I? I led you down the wrong path. Okay. So Pinkerton would eventually leave his role in military intelligence. I think this was in 1862 after McClellan, who had hired him, was demoted, essentially. He lost his whatever, not rank. Huh? Position? Yeah, I guess he lost his position as rank leader or whatever.
24:55Those are made up terms. Not going to be emailed by Civil War buffs at all. And then he said, all right, let me go back. You know, he still had his private detective agency. Rank leader. So let me go back to doing that. And I guess we can talk a little bit about some of the other innovations, you know, aside from hiring women to work as infiltrators and moles. And I believe we've talked about this in one of our crime episodes. Yes. Did we do one on mugshots or just? I think it came up. Criminal databases, maybe? Yeah, Alphonse Bertillon or Berlon, he in the 1840s came up with the idea of mugshots, fingerprints, using head measurements to basically create a database of criminals so that they couldn't pose as other people.
25:45And I guess that Pinkerton heard about this and brought it to the United States. Yeah, but when he brought it to the United States, he wanted to sort of codify it, I guess, and make it a more usable system and standardize everything. So he made all the pictures the same size. He essentially made little yearbooks. He got handwriting samples, and he would make these books, and he would send them out. And they called it the Rogues Gallery, and it was sort of the beginning of the United States criminal database. Yeah, and each picture had a senior superlative underneath it. So there is like most likely to unnecessarily shoot someone you're robbing in the knee.
26:24Stuff like that. That's good. I also saw that this was so sophisticated that it wouldn't be until the FBI was formed that something like a criminal database like this would be expanded upon, basically. Did you get a senior superlative? I did. Most likely to talk about criminal databases. Oh. Did I in reality? I don't think so. No, because my senior quote was leave me alone. We had fun ones and then real ones like official ones. And I got one of each. Oh, what were they? I got actually I got two of the unofficials. For the unofficials, I got best style. Oh, nice. That's really saying something in high school, man.
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27:12I guess so. I'm not sure how I won that one, actually. And then I got most fun on a date, which was very ironic because I literally dated one person my senior year and I was just the good friend to all the girls that I wanted to date. Wow. I was that guy. But then the official ones that were in the yearbook, best all around boy. Jeez, man. I see you in a different light now. Well, you know, it's pretty. I still got my T-shirt. I'll wear it occasionally. Best all around boy. Best all around boy. I think that's your new nickname. B-A-A-R-B. Well, best all around, technically. Oh, I say all around, but then again, I call Stovetop Hats.
27:57So, best B-A Barb, right? Yeah. All right. Just call me Barb from now on. Okay, Barb. I have a beloved aunt named Barb. I do too, or Emily does. So, she's sort of my aunt as well. Yeah, you can claim her. All right. So there's another thing that Pinkerton did to really kind of help establish his agency as like just nationally recognized and also kind of heroes. They were considered heroes across the United States because they went after bad guys and they usually got their man. They were very persistent and dogged. Sometimes they would pursue criminals for years. Yeah. Like it wasn't like, well, we tried for a month and we gave up.
28:42Like they would just keep going until they found the person. They would pursue them into Canada sometimes, into Mexico and beyond. And I guess one of the reasons why they were revered is because they had a code of conduct that was like strictly implemented. It was things like we will take no bribes, which is a big one at the time. Oh, yeah. Probably still is now. We'll never compromise with criminals. Yeah. We will partner with local law enforcement when possible. Okay. This one stood out to me. I thought this was kind of upstanding. They wouldn't take divorce cases or any case that could create a scandal for anybody.
29:23Yeah. I thought that was pretty cool. Yeah, pretty stand up. They also turned down reward money and he paid his agents pretty well, apparently. And this is just sort of business nuts and bolts. But he had a pledge to never raise fees without the client knowing. Like, in other words, I'm not going to hand you a bill at the end. That's not what we talked about. And also would just keep all of his clients very well informed. They had internal rules that were like, I think in the pamphlet, the general principles of Pinkerton's National Detective Agency. Mm hmm. They said things like the agent must be of a high order of mind, must possess clear and honest, comprehensive understanding, force of will, vigor of body.
30:05And you can't drink on the job unless you absolutely have to, as assumed, assumingly some part of like some mole situation where you're like, hey, do you want to go to the bar with this? Right. You better drink this rye whiskey or else we'll know you're a Pinkerton man. Exactly. They also, unless you had a direct order from your superior to, you weren't allowed to use alcohol to get like confessions or anything out of suspects. Yeah, like get someone super drunk. Yeah. Yeah. I mean, these are all pretty great like codes of conduct. For back then, totally, yeah. I did not see any stories of like rogue Pinkerton agents or that this was all just, you know, a whitewashing and they actually didn't behave like this at all.
30:50They do seem to have been pretty upstanding. And then so the other thing that really expanded the legend of the Pinkertons, and probably in part of why we still understand or know them today, is Alan Pinkerton wrote a bunch of books or at least published a series of books under his name that were like true crime detective stories. Yeah. This would have been in the 1860s, 1870s, I think. So this is like the dawn of detective stories. Yeah, I would think so. Remember when Poe wrote Murder in the Rue Morgue? Was that the first detective story? I don't know. But, I mean, it was early on in the going for sure.
31:29It was ahead of its time. Yeah. One of the most famous ones was the detective in The Somnambulist, right? Yes. And that is one in which he, as the character, and Kate Warren as her character, they catch a murderer. They go undercover, of course, and catch a murderer and a bank robber using a Pinkerton agent, as always, that posed as a ghost to get a confession. Yeah. I saw there was another one where Kate Warren posed as a fortune teller to get a confession out of somebody. Oh, that's pretty smart. Yeah. But these are like the books that they're saying, like, this is what we did. And I mean, like, if this was even remotely close, it must have been thrilling to have been a Pinkerton detective at this time.
32:12Totally. Because this is, again, when they were just a cause celeb in America, and did not have the blemished reputation that they have today. Yeah, and a book potentially being like a character in a book would be, you know, back then is sort of tantamount to like they made a TV show about us or something. Yeah, and we played like a semi-fictional version of ourselves or something like that. Yeah, exactly. One of the other things they were known for, Chuck, was nabbing outlaws in the Wild West because as the United States expanded westward and the frontier just kept going, it was a wild and raucous and lawless place.
32:52You might have a marshal. I know we talked about the marshal service serving as the law enforcement out west, but it was kind of far and few between. So the Pinkertons filled a real need at the time because one of the first things that developed after the Civil War was train robberies. Yeah, I mean, you got these, like you said earlier, it's a pretty good take when you rob a train and, you know, you get them out in the middle of nowhere, which is kind of the great the great thing about robbing trains. Everybody is you can just, you know, ride your horses up. You've seen all the movies in the middle of nowhere where there's no one around to help.
33:30But in this case, the Pinkertons are there. One of the first gangs that they got was the Reno gang. after the Civil War, they started robbing trains in Indiana and Missouri and banks and other places, but not from Reno, but they were the Renos, John Frank, Simeon, and William Reno. And in October 1866, for instance, they robbed the Ohio and Mississippi Express to the tune of$15 ,000 in 1866 money, which is a huge, huge haul, were arrested, But they posted bail and then started robbing again kind of right away trains and banks. And so the Pinkertons were like, we're on the job. I think the Adams Express Company was like, we've had enough.
34:14We've got to hire these guys. Yeah, in the two years that the Reno gang was active, they stole about a half a million dollars in 1860s money. Wow. That was a ton of cash. They were very successful. So, yeah, they definitely caught the attention of the train companies. Adams Express hires the Pinkertons, and they start hunting down the Reno gang. And this is a good example of them just using dogged persistence over and over and over again. They just kind of one by one captured the gang members. The first was John Reno, not Jean Reno from Twin Peaks. I had that same joke. They got him first. He may have been the leader as far as I know.
35:00They also caught a guy named Charles Roseberry, who was a member of the gang. And I don't know if they were expecting this or not, but the locals who were with them when they caught Charles Roseberry strung him up and hung him right there when they caught him. And I didn't see, like, what the Pinkertons thought about this kind of thing. Yeah. I mean, I think a lot of those guys were lynched and hanged. And, yeah, I don't know. I'm not sure if that's a good question, actually. If that was, I mean, obviously it wasn't his call, but after he hands them over, but I wonder if he was like, oh boy, I mean, how about a trial at least?
35:37Right. This doesn't seem to jibe with the code of conduct. Yeah, exactly. I also saw they recovered about$300 ,000 in cash in at least one instance. So you definitely got your money's worth when you hired the Pinkertons to nab Wild West train robbers. Yeah, I bet they weren't cheap, though. I tried to find out kind of how much they were paid, but if he was paying his agents well, which he supposedly did, but then I'm sure they were not a cheap hire. No. And then things kind of went pear-shaped for the Pinkertons. As far as I can tell, this was the first time the Pinkertons' reputation took a real hit.
36:11With the James Gang? Yeah, they went after the James Gang led by Frank and Jesse James. I didn't know this. Yeah. But they were terrorists, Confederate terrorists, during the Civil War in Missouri. That's where they were from. And Missouri was this powder keg that actually kind of helped kick off the Civil War because, I guess, abolitionists and pro-slavery people came together to settle Missouri, and they did not get along. And during the Civil War, one of the things the James Gang did was murder Union supporters in Missouri. Not even on the front lines. These weren't even soldiers. These were civilians.
36:49They were just running around killing and terrorizing. Yeah, for sure. And, you know, after the war, of course, they gained further notoriety by robbing everything in sight, you know, trains, banks, stagecoaches, you name it. And Jesse sort of built up this. Oh, what do you call it? Like a sort of legendary status among the poor and working class that he was some kind of a Robin Hood type, even though there's no indication that he was ever like robbing to give to the poor. Right. But people would, you know, hide them and take care of them and stuff like that for some reason. But at any rate, in 1874, the Pinkertons were hired to catch these guys, Frank and Jesse.
37:29And they sent an agent in to infiltrate the gang. His name was Joseph Witcher. And he did a pretty good job until they found out that he was an informant. And he was murdered, which kind of started the downhill tumble. Yeah, Alan Pinkerton took this quite personally. Oh, yeah. There's a quote from him saying that as far as capturing Jesse and Frank James, there's no use talking. They must die. So if they were wanted dead or alive, he was going to bring them in dead for sure. And in 1875, early on in the year, they went to the James's family home in Missouri. And Jesse and Frank James weren't home.
38:11They've been tipped off that the Pinkertons with a bunch of local pro-union supporters were going to be there to capture them. So they weren't there. But apparently the Pinkertons and their assistants didn't know this. Somebody, the Pinkertons said this was a local that did this, that they did not do this. Somebody threw a lantern into the home. I saw in the hopes of illuminating things better. Well, the lantern exploded. Yeah, exactly. The lantern exploded, killed their eight year old half brother, Archie and blew their mom Zerelda's arm off. So they've killed the young boy and maimed an older woman.
38:51And the Pinkertons are the ones who took the hit reputation wise. Yeah, and after all that PR work, a lot of that was undone because of this, basically. But it's not like they shut down or anything. And didn't they go after some other gangs, too? Yeah, very famously, they were the ones that chased Butch Cassidy and Sundance, the Sundance kid, down to Bolivia. The Bolivian army killed them. And they were famous for catching and summarily executing all of the members of the Apple Dumpling Gang. all right we'll take a break now okay i'm gonna contemplate that joke and we're gonna come back and talk about what the pinkertons were kind of known for from this point forward right after this
39:51new year new goals and in this economy a better money plan is more necessary than ever i am matt and i'm joel uh we are from the how to money podcast and every week we help you to spend smarter, save more, and make sense of what's going on out there. If you want 2026 to be the year you finally feel in control of your money, we're here to give you the tools and advice to help you make it happen. Listen to How to Money on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hi, I'm Dr. Priyanka Wally. And I'm Hari Kondabolu. It's a new year, and on the podcast Health Stuff, we're resetting the way we talk about our health.
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42:29Okay, so after the Wild West kind of came and went, they got into corporate affairs firmly on the side of the corporation. At the time, there was a lot of labor movements, a lot of workers' rights stuff going on. And don't forget, Alan Pinkerton had to flee the U.K. because he was such a radical labor supporter. Now his agency is the premier security group and labor organization infiltrators. This is what they started doing. And this is where the bad name, the blemish on their name that's still around today really started to develop because they would at this point do whatever corporations wanted them to do as long as they paid them.
43:19Yeah. And, you know, what corporations generally wanted them to do was bust up the unions, was to infiltrate the companies and bust up unions, which is what they ultimately started doing for, you know, a lot of money. It started out as an employee testing service in 1855 and sort of grew over the next few years. And initially it was like, hey, let's get some moles in there and see if we can uncover like illegal activity, people stealing from the company and stuff like that. But then it's understandable. Yeah, totally. But then that sort of expanded. And I guess the people hiring were like, hey, since you're in there, why don't you kind of let us know what's going on and what they're talking about?
43:59And like if they like management, if they're discontented and if they're, you know, most importantly, if they're starting to organize and talk about forming a labor society, which, you know, of course, would ultimately be a union. Yes, this became such a part of their job that the order of railway conductors started warning their members that there's Pinkertons undercover who are watching you and not just watching you to see if you're stealing. They're watching you to see if you want to form a union. And this was the I mean, this was a terrible direction for them to start to go down because this was such a militant time.
44:37I mean, there were like anarchists running around, like throwing bombs in the United States. There were labor unions that soldiers were sometimes brought out to shoot. I mean, it was a really rough time as far as like labor and management goes, because there was just this struggle to say who owns the fruit of our labor. You who's paying for the raw materials or us who's actually turning those raw materials into the end product. And maybe it's not one or the other, but I guarantee it's more than the share that you're giving us, factory owner. And so this struggle became violent many, many times.
45:16And again, like I said, the Pinkertons landed firmly or started out firmly on the side of corporations and they stayed there. Yeah, we should probably highlight the Molly Maguires. That was one of the more famous cases. They were a secret society in Ireland initially. And then in 1860s in Pennsylvania, kind of reemerged from Irish immigrants because they were coal miners there. And at the time, they were facing a lot of discrimination. The job conditions were not good. Working long hours, they were very dangerous. And they were, you know, a lot of times living in company housing, paid in company script that they could only spend at the company store.
45:53They were just completely folded into this corporation as almost enslaved people in some ways. Ultimately, they had their freedom, of course, but they were owned by the company, essentially. Finally, in the 1860s, supervisors started receiving these coffin notices, basically, from the workers saying, And, hey, we're the Molly Maguires, and coffin notice means that your time on Earth is nigh, and you're not going to be around very long. So the writing was on the wall that things were about to turn violent. Yeah, and it did start to get violent. And I saw that the Molly Maguires started murdering and assassinating some of the members of the corporation, like Foreman, who were the people they worked with the most directly and who were the most brutal toward them.
46:45But I also saw that this was in retaliation for members of the Molly Maguires being murdered first. Either way, it turned violent pretty terribly. What the Molly Maguires did not know is that there was a Pinkerton man who they knew as James McKenna, but whose real name was James McParlin, who had spent two years by now working undercover and ingratiating himself with the Molly Maguires, or even beyond the Molly Maguire, just the Irish coal miners who worked and lived in this area. So much so he became the secretary of the local lodge of the Ancient Order of Hiberians, an Irish Catholic fraternal organization.
47:24So he really worked his way into it. And he got a lot of intel on them and ultimately turned state's evidence and got 20 men executed almost exclusively on his testimony. Yeah, for sure. On charges of murder, arson, and kidnapping. Ten were hanged in 1877. Ten were then hanged in 1878, I guess. And this is one of the most insider jobs of all time. I think there was a historian, Harold Arand, who said it was one of the most astonishing, astounding, excuse me, surrenders of sovereignty in American history. Because what happened was Franklin Gowan, who was the guy who ran the company who hired the Pinkertons to begin with, he was the chief prosecutor.
48:19So it was all this inside job. These guys were arrested by a private police force. And then the coal company's attorneys prosecuted them. And the only thing that the state did was like, here, use this courtroom and use our gallows or whatever. And other than that, it was all just a private job to like find and execute these guys. Yeah, many of whom who were considered to have been innocent. They were innocent men who were executed. Again, almost exclusively on James McParlin, this Pinkerton man's testimony. And yeah, it was just a total travesty from start to finish. And Pennsylvania did pardon one of the men, John Kehoe, in 1979, about 100 years too late for John Kehoe.
49:04But it was kind of a symbolic thing saying like, yeah, we really screwed up in letting this company essentially form their own court and trial and executions. Probably more famous, though, is the Pinkerton's role in the Homestead strike in Homestead, Pennsylvania, at one of the Carnegie steel mills. Yeah. So in 1892, there was a union contract that expired for that steel company in Pennsylvania there in Homestead. And Henry Clay Frick and Andrew Carnegie, a couple of robber barons we've talked about in the past, said, all right, we're going to cut wages back. We're going to break this union, which was the Amalgamated Association of Steel and Iron Workers.
49:46And Carnegie said, I'm out of here. I'm going to leave the country. Henry Clay Frick got involved sort of doing the dirty work on the ground. Yeah. And he said, all right, I'm going to hire the Pinkertons. We're not even negotiating yet. I'm going to bring these guys in to essentially act as guards to lock these people out. Yeah. And so 300 Pinkertons showed up on July 6, 1892. They were pulled down the river on barges and they were all armed to the teeth with Winchester rifles and Colt 45s and all the modern guns you could hope for. And when they arrived, they were met with, I think, two or three thousand homestead, not just steelworkers, but neighbors, community members, just people who were supporting the strikers.
50:36Angry, too. Yeah, they were really mad, not just because they were in the midst of the strike, but because this private police force had shown up to intimidate them or possibly kill them the way that they were armed. And so a battle ensued like there's no other word for it. It was a 12 or 15 hour battle. yeah um only a dozen people died but it that's amazing to me as violent as this battle was they tried to they or i should say they pushed a flaming train car at the barges to try to kill the pinkertons like that was just one thing that the strikers did like it was really violent yeah i mean it is shocking that only a dozen people died uh i guess it's a testament to how bad of a shot they were.
51:22Yeah, it really was. Collectively. Of course, the workers, you know, they surrendered, the Pinkertons did, because they were just so far outnumbered, even though most of the, I think most of the dozen were the workers that died, but the Pinkertons knew that they were vastly outnumbered. Yeah. So they surrendered, but the workers lost because Henry Clay Frick, man, I have a hard time with that one. You keep wanting to say people. I know, Henry Clay people. got 8 ,500 National Guard troops sent in after the Pinkertons left. And of course, you know, they broke the union and said, we're going to decrease your wages.
51:56We're going to increase how much you have to work. And this just became sort of a cyclical thing that was happening. The Pinkertons, early on, they were pretty good at infiltrating. But when it came to breaking these unions, the federal government would come in with the troops and do a far better job at doing so. Yeah, because strikers typically recognize federal troops as more legitimate than a private police force showing up, you know? Yeah. And just more people with more arms. Yeah. They had Gatling guns, like as demonstrated at the end of the Wild Bunch. That's right. You don't want to mess with those.
52:32So, yeah, from those of us like looking back today, you might think, well, that's just what they did back then, which is messed up. But that's just the norm. Not true. Congress actually investigated this incident. They were like, that is pretty screwed up that you hired the Pinkertons and brought in the National Guard to essentially put this town under martial law. And as a matter of fact, Congress urged states to like pass laws to make it so that corporations couldn't hire private companies to break unions. And Ohio went so far as to say the Pinkertons themselves are now illegal here. Yeah. Yeah, that's true.
53:10So, I mean, that really changed everything for the Pinkertons there. As far as strike breaking goes, it took a huge hit. Couldn't get a lot of work after that. But they did go on. They did anti-union espionage work, of course. This is something I never knew at all, was that they just kept going. They were acquired in 1999 by Securitas. And I had no idea that they went on that much further after Pinkerton's death, after Alan Pinkerton's death. Yeah, they trade on the name still, for sure. But it's a massive company, I think, with like 50 ,000 employees and offices all over the world. But they still use the Pinkerton name, like you can hire Pinkerton for corporate security.
53:54Apparently, they'll ride along on container ships to protect against pirates. They've served as guards at Marilyn Monroe's funeral back in the 60s. I also saw that same year they escorted the Mona Lisa from France to the U.S. Wow, which is, you know, they could probably just do that under an overcoat. That thing's pretty small. It is fairly small. And then one other thing where they pop up, and this made me wonder if this is where this idea came from. Apparently, they're bad guys in the video game Red Dead Redemption 2, which I know for a fact that you've played. They very much are, figure very heavily into that storyline if you play the story part of that.
54:34Is that where you got the idea to do one on them? No, because I haven't played that in a long time. I'm not sure where I got it. It may have been, I don't know. I'm not really sure. They also figure in a bunch of movies, of course. They were in Deadwood. They were in The Long Riders in the 80s. And friend of the show, Paul Schneider, was in the great, great movie from 2007, in the assassination of Jesse James by the coward Robert Ford, and the Pinkertons figure pretty heavily in that movie, too. That was a good movie. We should talk about the death of Alan Pinkerton real quick, Chuck. Yeah, it's pretty unusual.
55:11He died July 1, 1884, right before his 65th birthday. And as the story goes, he slipped on a street in Chicago and bit his tongue, something which I did when I was a kid. I had 12 stitches across the center of my tongue, to put that thing back together when I was like 12. But I did not die because I'm still here. But Pinkerton died as a result of this because it turned gangrenous. Yeah, he wouldn't go get it treated, and it just kept getting worse, and that was it for him. Yeah, he was put to rest near his wife. And very interestingly, he also, in his family plot, buried Kate Warren because he's so admired.
55:55The first female detective ever hired. He so admired her and her work that he had her buried with him. She was still alive and was very unhappy about this, but he admired her that much. That's super cool. So she's there with him. Maybe I guess some of his sons are there and his wife, Joan. Yes. Wonderful. Nice, Chuck. You got anything else? I got nothing else. That's it for the Pinkertons, everybody, at long last. And since I said it long last, I just triggered listener mail. That's right. There's a little follow-up on the GPS episode. Toward the end, I kind of poked fun at Garmin as being something that, you know, like my mom uses and not like a more modern system.
56:39But it turns out Garmin is still very popular because Deanna sent me an email saying, hey, a lot of cyclists use this stuff. And I asked her why. I was like, oh, that's super interesting. I said, do you know why they're used by cyclists who are still around in that capacity? And she said, good question. I think there are a couple of reasons why it's still the go-to for GPS. They've been around forever. They've been making GPS for planes and boats since the late 80s. So they had a really big head start. And then number two, constant refinement. While others are just starting to develop their products, Garmin was already fine-tuning theirs, and they had a 20-year head start, so they packed in a ton of extra features.
57:16For example, they introduced the first bike radar system years before anyone else, and the radar still blows the competition away. I even have a buddy who works for Wahoo, and he still uses a Garmin radar. Very nice. Also, Deanna says they built a lot of brand loyalty, especially in the cycling world. Many of us still use them, even though the quality has slipped just a bit in recent years. We don't like using phones on our bikes because they're bulky and drain the batteries really fast, and Garmin just feels more polished and reliable for our needs. Who was that from? That was from Deanna. Deanna Garmin?
57:52That's right. Thanks, Deanna. We appreciate that. That was a great email. And if you want to be like Deanna, you can email us too. Send it off to stuffpodcasts at iheartradio.com.
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58:42the most important issues to focus on, and the small moves that make a big difference. Kick off the year with confidence, listen to How to Money on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I'm John Polk. For years, I was the poster boy of the conversion therapy movement, the ex-gay who married an ex-lesbian and traveled the world telling my story of how I changed my sexuality from gay to straight. You might have heard my story, but you've never heard the real story. John has never been anything but gay but he really tried hard not to be. Listen to Atonement, the John Palk story on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts.
59:27Hi, I'm Dr. Priyanka Wally. And I'm Hari Kondabolu. It's a new year and on the podcast Health Stuff we're resetting the way we talk about our health. Which means being honest about what we know what we don't know and how messy it can all be. I like to sleep in late and sleep early. Is there a chronotype for that or am I just depressed? Health stuff is about learning, laughing and feeling a little less alone. Listen on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts. This is an iHeart Podcast. Guaranteed human.
From the publisher
The Pinkertons became the most famous detective company in the U.S. But were they noble or notorious? We get to the bottom of it all in today's episode.
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