Infamous America - KIDNAPPINGS Ep. 5 | Charles Ross: “Random Bad Luck”

Episode Date: October 22, 2025

72 year old Charles Ross was a year into his peaceful retirement after a lucrative career in real estate, followed by President of the prominent George S. Carrington greeting card company, when he found himself at the wrong place at the wrong time just outside of Chicago. John Seadlund, who’d been influenced by John Dillinger’s gang member Tommy Carroll and who had evaded the FBI for years, stole much more than Ross’s golden years leading FBI Director J. Edgar Hoover to manage the investigation personally. The case would earn Seadlund the nickname “The Nation's Cruelest Criminal”. Join Black Barrel+ for ad-free episodes and bingeable seasons: blackbarrel.supportingcast.fm/join   Apple users join Black Barrel+ for ad-free episodes, bingeable seasons and bonus episodes. Click the Black Barrel+ banner on Apple to get started with a 3-day free trial.   On YouTube, subscribe to INFAMOUS+ for ad-free episodes and bingeable seasons: hit “Join” on the Legends YouTube homepage.   For more details, please visit www.blackbarrelmedia.com. Our social media pages are: @blackbarrelmedia on Facebook and Instagram, and @bbarrelmedia on Twitter. Learn more about your ad choices. Visit megaphone.fm/adchoices

In 1938, FBI director Jay Edgar Hoover labeled John Henry Seedland, the nation's cruelest criminal. That was no easy distinction considering the infamous criminals who had made names for themselves over the past few years, like Leopold and Loeb, Bonnie and Clyde, John Dillinger, Babyface Nelson, Machine Gun Kelly, and the Barker gang, not to mention the kidnappers who had killed the Lindbergh baby and Brooke Hart. Al Capone had led a bloody gang war in Chicago, and Lucky Luciano had been instrumental in a bloody mob war in New York. But J. Edgar Hoover had applied the label of nation's cruelest criminal to John Seedland. To be fair to Hoover, there was probably a lot of recency bias in the pronouncement. By 1938, all of those other famous criminals were dead or in prison.

Coming up behind them was John Seedland, who, according to the story, was directly influenced by a soon-to-be member of the Dillinger gang. Seedland grew up in the woods around Ironton, Minnesota, a small town that sits right in the middle of the state. And at that time, likely in April 1933, he was particularly susceptible to romanticize stories of crime. In the past five years, his life had gone from difficult to really rough. After he graduated high school in 1928, he worked with his father in the local iron mines and mechanic shops. One year later, the stock market crashed, and John was laid off. He bounced around the region looking for steady employment before he finally moved back home with his parents and worked part-time jobs at small local businesses.

Then on March 23, 1933, John's father was found dead in his car from carbon monoconical. side poisoning. Shortly afterward, John was duck hunting in the woods when he stumbled upon a gangster named Tommy Carroll. By 1933, Tommy Carroll had been in and out of jail for 13 years. He started his criminal career at the age of 20 in 1920, not long after he returned from service in World War I. In 1927, he was convicted of armed robbery in Missouri. He was paroled in 1931, and for the next year and a half, he essentially disappeared. He popped up on the grid again in May, 1931, in St. Paul, Minnesota, when he was arrested for possessing burglary tools. But sometimes shortly before his arrest, he spent a few days hiding in the woods a couple hours north of St. Paul. When John Seedland

discovered a hardened criminal hiding in the woods, he gave no thought to turning the man in. Instead, he wanted to help. He brought Carol food. and happily listened to whatever stories Carol was willing to tell. Tommy Carroll's stay was likely brief, but possibly powerful. Tommy Carroll was killed during a shootout with police in Waterloo, Iowa, one year after he left the woods of central Minnesota. A month later, as if taking up Tommy Carroll's mantle, John Seedland robbed a restaurant in Minnesota.

It was a feeble attempt and quickly landed him in jail. But 10 days later, Seedlin escaped from jail and he never looked back. He never went home and he never returned to his old life. John had always been a loner. He never wanted friends and he never participated in activities at school. When he had finally joined a youth hockey team and showed immense skill and potential, he turned down an offer to go pro. It could have been a ticket to a different life,

but instead he stayed in Ironton, worked with his dad in the the mines, suffered through the Great Depression, and then the death of his father. Now, he was embarking on a life of crime. He was somewhat successful when he worked alone, but when he brought in a partner and they got into the kidnapping racket, it all went very bad. From Black Barrel Media, this is infamous America. I'm your host, Chris Wimmer, and this season we're telling stories of some of the most notorious kidnappings in American history, the crazy events which surrounded each abduction in the chaotic investigations of the cases. This is episode 5, Charles Ross, random bad luck.

For three years after John Seidlin escaped from jail, he crisscrossed America leaving a trail of stolen cars and robbed banks in his wake. Each crime followed the same pattern, strike fast, disappear, and resurface in another state. He changed his name and did it all over again before the dust could settle. Law enforcement was always a step behind, as Seedland's constant movement and his calculated false identities kept him elusive. When absolutely necessary, he'd disappear into the wilderness and survive for weeks on raw rabbits. John Seedlin would never be a headliner like John Dillinger, but his criminal spree seemed unstoppable, until he received a small dose of his own medicine in June 1937.

Outside Superior Montana, 27-year-old John Seedland picked up a 20-year-old hitchhiker named James Gray. Gray asked to take a nap in the back of John's car, and John agreed. But when James discovered a gun wedged between the seats, the tables turned. James pulled out the weapon, forced John to hand over his money, and prepared to steal the car. As James slid into the driver's seat, John threw a vicious weapon. punch and knocked out James. John could have abandoned James on the roadside, but he didn't. The kid had guts and nerve, attributes John knew could be useful in his criminal enterprise.

So he loaded the unconscious James into the car, and within 48 hours, they struck an uneasy deal. They would be partners in crime, but never friends. It was a business relationship, and business did not go well. When John picked up James, he was in route to Wisconsin to rob a bank. After forming their partnership, their target remained the same. But soon after arriving in Wisconsin, their plans unraveled. They heard of an intriguing opportunity involving six women traveling by truck with a box

rumored to contain valuable jewelry. The tip redirected their focus. They ambushed the truck, seized the box, and took one of the women hostage. But five miles down the road, they opened the box to discover a cruel joke. Instead of jewelry, they found candy. They released the woman unharmed, but it was a frustrating start to their partnership. The pair moved on to Lake Geneva, Wisconsin. On September 2, 1937, new intel pointed them to a cafe owner

who was rumored to have more than $100,000 in fine jewelry. One night, they tailed the cafe owner and he, his wife, forced them off the road, and kidnapped the wife. After two days of failed ransom negotiations, they had no choice but to abandon the plan. They released her unharmed, and once again, they walked away with nothing. Their next target was a wealthy businessman in Decatur, Illinois. John and James planned to abduct the man from his home, but when they arrived, they discovered he was out of town, which left them empty-handed yet again. That third failed to. attempt finally led them to research their next move more carefully. This time, they set their

sights on a famous Major League baseball player named Jay Hanna Dean, though he also used the name Jerome Dean. He was better known by his nickname, Dizzy Dean, and he had helped the St. Louis Cardinals win the 1934 World Series. But John and James abandoned the idea almost as quickly as they made it. To collect ransom money from a famous baseball player, they would need to involved the baseball club, which risked drawing too much attention. That made four failed robberies and kidnapping plans within three months. John and James were growing desperate. They needed a win, and they needed it soon. It finally came on September 25, 1937. They were on the outskirts of Chicago when they decided to use the same strategy they had used with the cafe owner. By all accounts,

the next plan was completely random and spontaneous. They watched a 72-year-old man named Charles Ross and his secretary Florence walk out of a restaurant and get into Charles's car. John and James decided to force Charles to pull over to the side of the road and then they would kidnap him. Charles Ross had made a small fortune in real estate before he became the president of the George S. Carrington Company, a successful business which made greeting cards and games.

In 1936, Ross retired from the Carrington Company with a load of stock options. During the first year of his retirement, the company had been slowly paying him for his shares. So each week, he met with his former secretary, Florence, for an update. That night in late September, 1937, they ate dinner at a restaurant on the outskirts of Chicago, and then started the drive back to the suburb of Franklin Park. Shortly after they started the drive, a car started trailing them with its headlights glaring through their windows. Charles remarked to Florence that he didn't like the look of the situation and he was going to pull over to let the car pass. Charles pulled his car onto the shoulder of the road and James Gray abruptly swerved the kidnapper's car in front of Charles' vehicle.

James slammed on the brakes and John leapt out of the passenger sign. He had a gun in his hand, and he marched up to the driver's door of Charles's car. John tugged at the car door, but it was locked. He tapped his revolver against the window and threatened to shoot if Charles didn't open the door. With no alternative, Charles unlocked the door. John grabbed Charles, frisked him for weapons, and declared, This is a kidnapping. Florence pleaded frantically with John.

She said Charles had health problems, including a weak heart. But her babbling only irritated John. His patient snapped. He shoved the gun against her shoulder and demanded, What are you to him, his daughter or his sweetheart? She stammered that she was just a friend, and then John pressed her about money. He asked, how much can he give us?

Half a million, a quarter of a million? Florence said she didn't know what Charles was worth, but she offered him the cash she had on her. John took her $85, but he still forced Charles Ross into James's car. Then he ordered Florence to keep her head down until they were gone. If she called the police, they would kill Charles Ross.

Florence crouched down in the passenger seat of Charles's car and listened as the engine of the kidnapper's car faded into the distance. Then she peeked over the dashboard and made an unexpected decision. When she judged that their taillights were far enough away, she slid over into the driver's seat and started to follow them. For a time, she kept pace while staying far enough back to avoid detection. But eventually they outmaneuvered her, so Florence pulled over at the first safe place she could find and called the police.

Her immediate eyewitness recollections were invaluable. She recounted all the details of her interaction with the kidnapper, and she described John's face, young and nervous, with curly brown hair and a sharp angular profile. She helped as much as she could, but John and James had a good head start. While Florence spoke with the Chicago authorities, the kidnappers were driving northeast through Illinois and Wisconsin before stopping deep in the woods of Emily, Minnesota.

The remote location was a perfect hiding spot, and over the next two days, the kidnappers strategized their next move. They forced Charles Ross to write the first ransom note. John Seedland hovered over. Charles' shoulder and dictated the words. Charles attempted one subtle bit of resistance when John told him to write a demand for $50,000. Charles wrote $5,000 instead, and John grabbed the note and added an extra zero. With that, the letter was done, and they mailed it to Harvey Brackett, one of Charles's business colleagues in Green Bay, Wisconsin. A second ransom letter arrived shortly after the first. The second

letter outlined details for the ransom drop. It said the $50,000 should be in non-consecutive unmarked bills in denominations of fives, tens, and twenties. The bills were to be delivered in a small leather bag by a Harley Davidson employee, dressed entirely in white, who was supposed to drive a motorcycle to a designated place and then abandon it with the money. Lastly, the letter provided instructions for agreeing to the demand by placing a notice in a Chicago newspaper. Harvey Brackett contacted Charles' wife, and they brought in the FBI despite the kidnappers' demand to say nothing to anyone. After the passage of the 1932 Lindbergh law, the FBI had plenty of grounds to get involved directly. Kidnapping was a federal crime, and in Charles Ross's case,

even though the FBI couldn't confirm it at the time, the kidnappers had crossed state lines during the commission of the crime. For now, John Seedland and James Gray were in control. But John's obsessive need to maintain control over every little detail led to escalating tension between all parties. And then disaster. The Ross family placed the notice in the newspaper agreeing to the ransom demands. But then John Seedland kept going.

He had purchased a typewriter, and over the next few days, he sent three additional letters. This time he bypassed Charles' immediate family and sent them to Elton Armitage, another associate of Charles Ross. John's stipulations became increasingly specific. He outlined a 395-mile route for the motorcycle driver to deliver the ransom, and forbade the driver from using a side car. Next, he specified exactly how many of each type of bill, fives, tens, and 20s, should be in the ransom money. John knew proof of life was critical to maintain credibility, and he made the reveal elaborate. He directed Elton Armitage to a camera shop on South Wabash Street in Chicago. There, Armitage would find ten rolls of film waiting for him.

When the film was developed, they would have proof of life. The FBI developed the film and found eight photos showing Charles in the woods, holding the October 2nd, 1937 edition of the Chicago Tribune newspaper. He wore the same clothes from the abduction eight days earlier, but by the time the images were seen, it was October 6th, four days after the pictures were taken, and 12 days after the kidnapping. The FBI and the Ross family had to hope Charles was still alive,

because they would receive no further proof. The final letter arrived on October 8th, and had set the ransom drop for that same evening. The FBI had no leads on the location of Charles Ross and no choice but to follow John Seedland's increasingly elaborate plan. As instructed, an employee dressed all in white, drove a Harley Davidson motorcycle along the entire 395-mile route in Illinois, and then abandoned the bike and the money in the designated spot.

John recovered the $50,000 ransom with little, interference and drove back to Emily, Minnesota. John took $30,000 of the ransom money, and James received 20. The arrangement reflected their pre-established agreement, with John receiving a larger share for his role as the mastermind behind the operation. So then it was all over. All that was left to do was released Charles Ross. But Charles wasn't released, and the story was far from over. John Seedland had stated in the ransom letters, that Charles would be released within 48 hours of the ransom drop. Rather than following through on the promise,

John decided they needed to relocate to a second hideout near Spooner, Wisconsin. On October 10th, around 7 a.m., the group arrived at their second hideout. It was similar to the first in that it was deep in a maze of forest, but it had a frightening new feature, a pit carved into the ground, which was large enough for bodies. As John and James led Charles over to the pit, tension rose between the kidnappers. It's not clear of James knew about

or agreed with the plan to move to a second hideout, and it's possible he became agitated about the dark turn that the kidnapping could take. An argument erupted, and John believed James was about to attack him. The argument quickly escalated into a struggle which involved all three men. One of the two kidnappers had a gun,

though it's hard to know which one in the early stages. But as they fought, they all fell into the pit. John Seedlin gained control of the gun, and he fired a shot at his partner James Gray. Charles Ross had apparently been knocked unconscious during the fall. And now, with James badly injured and Charles unresponsive, John fired several shots at James and finished him off. John tried to revive Charles, but Charles didn't move or wake up. John thought Charles was dead, and he fired a single shot into Charles Ross's head to be sure.

At least, that was John Seedland's version of events. It was a strange mix of self-defense, mercy killing, and cold-blooded murder. Prosecutors would put forward a different theory, though it wouldn't change the result of Seedland's actions. By 5 p.m. on the evening of October 10, 1937, 20-year-old James Gray, and 70s. 72-year-old Charles Ross were dead, and 27-year-old John Seedland was on the run with $50,000. John started criss-crossing the country to avoid capture. His first stop was Northern Minnesota, where he buried $32,000 in ransom money in a typewriter box. Then he drove across North Dakota, Montana, and Idaho until he reached Spokane, Washington. There, he abandoned the car he had used in the

kidnapping and stole a new one. After that, he drove down to California. Meanwhile, the Ross family and the FBI were in Illinois, waiting for word of Charles's release. The 48-hour timeline for his release came and went. The rest of the week passed with no contact from the kidnappers. On October 18th, eight days after Charles was killed, his wife issued a decisive warning to the kidnappers. She announced publicly that unless Charles was returned immediately, quote, all law enforcement officers would make vigorous efforts to locate and punish those responsible.

The next day, there was silence. With no response from the kidnappers, the FBI activated all available resources to track them down. As with the previous major cases of the era, the agency started to follow the money. For the next three months, agents tracked the random. some money as John Seedland blazed a trail through the country on his spending spree. He had crisscrossed the northern U.S. from Minnesota to Washington right after the ransom drop. Then he went down through Oregon to California. Then he headed east through the mountain states to Illinois and on to Pennsylvania and New York. From there, he turned south again

and drove down to Florida. Each time the FBI got close, John vanished. But John had a fatal weakness. He loved gambling, especially at racetracks. Fueled by the ransom money, he could now place brazenly large bets, and the temptation became impossible to resist. He was confident that the FBI was pursuing him, but he hadn't seen an agent during his three-month journey across the country. So, John believed he had outrun the law. He thought he could slow down and indulge a few bets. But what John didn't know was that he may have outrun the agents, but he had not outrun the the FBI money tracking technology. It had advanced greatly in just the past five years since the Lindbergh kidnapping. Every time he made a bet at a racetrack with ransom money, the FBI knew about

it. And the breakthrough came in early January, 1938. The FBI discovered ransom money, consistently turning up at the Federal Reserve Bank in Los Angeles. The bank traced the money to the Santa Anita racetrack, one of the most popular horse race track, one of the most popular horse racing venues on the West Coast. FBI director Jay Edgar Hoover personally flew to Los Angeles. Hoover wasn't about to let a fugitive they'd been pursuing for months, slipped through his fingers again. On January 14th, the FBI staged a massive sting operation at the Santa Anita Racetrack. Hoover's team coordinated with the racetrack to have special agents serve as what were called change carriers. An agent stood behind every bedding

wicket to inspect each bill that was used to place a bet. The agent compared the bills to the serial numbers of the ransom money to try to find matches. On the day of the sting, $400,000 to $1 million passed through 500 ticket sellers and 500 cashiers. All of them were under surveillance, and every bill was checked by the FBI. Undercover FBI agents were also positioned throughout the venue, standing ready for the signal that a ransom bill emerged. When the signal was finally given, they swarmed a man named Peter Ander, who had nonchalantly placed a bet on a horse.

A search revealed that he had more than $14,000 in cash on him, and all of it was ransom money. The FBI didn't know the identity of the kidnapper, and agents had never seen the man in person. The only information they had about him was the physical description which had been provided, by Charles Ross's secretary Florence. The man calling himself Peter Ander was calm but defiant.

He denied involvement in the Ross kidnapping, though he admitted to knowing the money was from a crime, and he pinned the blame on a bank robber acquaintance. Hoover was in no mood for games, and he personally interrogated Peter Ander. The truth unraveled after hours of questioning. Peter Ander was, of course, John Seedland, and he eventually confessed everything in a 28-page statement.

The confession only deepened the horrors of the case. When asked about Charles Ross's health status and location, John casually admitted, dead, of course, I shot him. I also killed the fellow with me, a punk named James Atwood Gray. They're dead in a hole up in Wisconsin. It was a freezing cold January in Minnesota, and the ground was covered in thick snow. Even so, FBI agents found themselves trudging through the backwoods, led by a handcuffed killer, shackled to two agents.

The FBI was on a mission to recover the bodies of James Gray and Charles Ross, and to recover ransom money, which John Seedland said was buried somewhere in the northern part of Minnesota. The winter landscape looked vastly different than when John had buried the money in September. But after diligent and frigid searching, they found the buried. typewriter box, which contained $32,645. Added to the money they found on John when he was captured, the FBI had recovered $47,000 of the $50,000 in ransom money, and the recovery was a big step toward proving John Seedland told the truth during his confession. Following his directions, agents headed to Emily, Minnesota, and found the first hideout buried under snow and branches. It was a bleak

space where Charles Ross had been held for two long weeks. Now there was one final challenge. Agents followed John deep into the Wisconsin woods, where worsening weather forced them to trade in their vehicles for horse-drawn sleds. On January 20, 1938, the convoy pushed through miles of frozen terrain with seedland warning them of the difficulties. Eventually, they reached the second hideout. And the pit, which had been dubbed the Death Chamber. Beneath layers of snow and brush, FBI agents unearthed the pit, which confirmed the final part of John Seedlin's story. Lying face down, riddled with bullets, was James Gray. Nearby, Charles Ross lay with a single bullet wound to the head, though the autopsy later revealed two skull fractures and several broken ribs.

agents secured the bodies and made the trek back to Minnesota. On January 24, 1938, Seedland was transferred to Chicago, where he faced a federal grand jury on February 1st. The charges were read out meticulously, kidnapping, ransom collection, transporting victims across state lines, and the murders of James Gray and Charles Ross. Seedland was emotionless and he pleaded not guilty. But on February 28, he changed his plea to guilty, though he attempted to argue that he wasn't responsible for Ross's death. Seedlin claimed Ross had already succumbed to injuries from a fall before the gunshot. It didn't matter. John Seedlin was convicted on all counts, and he received the death penalty. He was executed in the electric chair in Illinois five months later on July 14,

1938. It was the second execution since the Lindbergh law went into effect, with the first being the man who was convicted of the Lindbergh kidnapping, Bruno Houtman. At the time of Seedlin's death, FBI director Jay Edgar Hoover labeled him the nation's cruelest criminal. Seedlin's death solidified the fact that certain aspects of the case will remain mysteries forever. He was the only survivor of the two weeks in the woods of Minnesota and Wisconsin. No one will ever know exactly why he moved the group to Spooner, Wisconsin, after he had the ransom money. Seedland claimed James Gray attacked him and tried to kill him, and that was what led to

the struggle by the pit and the subsequent murders of Gray and Charles Ross. Prosecutors countered that John Seedland was a cold-blooded murderer who killed James Gray out of simple greed, and then killed Charles Ross to a limit. the only other witness. The outcome was the same, but John Seedland took his motives to his grave. Next time on Infamous America, in the final episode of our series on kidnappings,

when the youngest child of Kansas City's wealthiest automobile dealer gets abducted. The story that follows is total chaos, fueled by greed and addiction, and it leads to the largest ransom request in American history up to that time. That's next week on Infamous America. Members of our Black Barrel Plus program don't have to wait week to week to receive new episodes.

They receive the entire season to binge all at once with no commercials, and they also receive exclusive bonus episodes. Sign up now through the link in the show notes or on our website, blackbarrelmedia.com. This episode was researched and written by Mandy Wimmer, original music by Rob Valier. I'm Chris Wimmer. Thanks for listening.