Saturday, April 21, 1934. Rutland, Vt. 14 year old Raymond Webster is walking around Rutland’s Pine Hill area when he finds a newspaper protruding oddly from the ground. But this is no an ordinary piece of litter — there was something strange about this find. Beneath the paper, the dirt seemed to be fresh, as if something were buried beneath it.
Curious, Webster returns later with a few friends. They manage to extract two boxes from a shallow hole, both wrapped in newspaper. But their wonder is short lived when, almost instantly, two strange men suddenly emerge from the nearby woods and walk towards them. Fearing for their lives, the boys drop the boxes and run.
The strange men call after them and order them to stop, but the boys kept running. Seconds later, they hear the sound of gunfire.
What Webster didn’t know at the time was his terrifying encounter wasn’t unique. Something odd was happening in Rutland in April 1934; other residents noticed it, too. They also began to notice a group of visitors who suddenly appeared in the community — a group whose seemingly strange behavior distressed whomever encountered them.
On April 26, 1934, the Rutland Herald ran this front page headline: “20 mystery sleuths upset Rutland’s calm.” The story revealed that the skulking intruders were FBI agents. Now, concerned residents all had one question on their minds: What was the FBI doing in Rutland?
The Herald and the local authorities weren’t talking — mostly because neither had any answers. The rumors began to spread. Kidnappings, extortion or illegal narcotics all seemed like plausible explanations.
But as details about the FBI’s presence slowly began to leak out, the situation took a turn for the bizarre. The Herald reported they were ordered to keep quiet about the FBI’s arrival until two days after the fact.
When the local police contacted FBI offices to inquire about it, they were told that the agents were only taking instructions from Washington, and any additional information was classified. Local police were then instructed to carry out any arrests the FBI agents called on them to make — without question.
Around the city
Rutland residents soon began to notice that the agents were focusing their investigations on the area of the city around the Rutland Country Club and Pine Hill. People began to speak eagerly of their sightings. Residents saw agents lurking around the country club, and another staking out the area with a pair of binoculars from atop a silo on Grove Street.
Others reported seeing agents using the barn at the Fitzgerald farm on Grove Street as some sort of base camp. Agents were seen entering the barn and exiting shortly after wearing different clothes.
According to some witnesses, agents would return at least four times a day to change their clothing and leave again. These clothing changes appeared to be part of some undercover operation where agents were disguising themselves as hobos, like those who frequented the local railroads and hitched free rides on from Rutland to Ludlow.
Over in Proctor a West Rutland resident recalled a bizarre encounter of his own, which was thought to be related to the mysterious activities in Rutland. One night, as he was hitchhiking on Route 3 in Proctor, he approached a car on the side of the road near a bridge. Concealed by bushes and the shadows of the night, the vehicle would have never been visible unless another car hadn’t driven past with its high beams on. When the lights illuminated the suspicious vehicle, he noted four men inside the car, waiting for something unknown.
What was going on here? Who or what were they looking for?
While paranoia spread throughout the community, the FBI began to seek out certain individuals for questioning. Among the first to be questioned was Webster, whose startling encounter near Pine Hill had piqued the Feds’ interest.
What was so important about those mysterious boxes buried near Pine Hill? Speculations abound. Soon, there was little distinction between fact and myth. One rumor held that federal agents were trying to catch an extortionist who had been told that there would be ransom money waiting for him at the country club — in the exact spot where Webster found those strange packages.
Another theory posited the agents were sent to Rutland to prevent a kidnapping. The alleged kidnappers were said to have used the Rutland Country Club as a drop site for the ransom money. With the Lindbergh kidnapping captivating the nation at the time, an extortion case in Rutland seemed easy to believe.
After Raymond, FBI agents brought in 28 other young men for questioning at the local federal building. Cloaked in secrecy, the Herald dubbed these interrogations the “Star Chamber Sessions.” The boys’ parents were prohibited from attending these meetings.
Soon, caddies from the Rutland Country Club and several more young men were also brought in for questioning. The interrogations weren’t random; the Feds were looking for someone.
Rumors began to circulate about these clandestine hearings. It was said that everyone who was brought in was fingerprinted and asked to produce a specific writing sample for the agents. The content of the sample was revealed on April 27 when the Herald printed the full text of the cryptic note on the front page. It read:
“If you were co-operate in giving your fingerprints and help us out, it will make the country safer for you and your family. If you meet us at Union Station in Albany on Thursday, Friday or Saturday of the last week in April, your troubles will be over and we will never trouble you again. On your arrival in Albany, you will receive $1,000 for your troubles.”
What did this odd message mean? Why were all who were brought in for questioning required to rewrite it? And what did the FBI intend to do with it?
On April 28, Rutland’s mystery gained national attention as out of state papers such as The New York Times began reporting the story, calling it “The Pine Hill Mystery.”
More puzzling events
Strange things kept happening, and everyone was speculating. Supposedly, a man approached a Rutland businessman and made him a suspicious offer. He offered him $40 for every $100 in $5 and $10 bills he circulated around the city. Naturally suspicious, the businessman went to alert the police, but before he could, the mystery man had disappeared.
Up the road in Forest Dale, a local man made another alarming discovery — this one far more sinister. Reports of explosives concealed in a mattress were found on the side of the road. According to police, they found two tin cans filled with a grayish powder inside. The amount of powder was enough to level a large city block.
Who left these explosives on a back road in Forest Dale? Were they forgotten, or were the mysterious owners planning on coming back for them? Most importantly, were they related to the FBI’s presence in the area?
Eventually, the FBI agreed to reveal that they were sent to Rutland to investigate mysterious notes that were sent to the Bureau. Though the Feds refused to release the name of the target, they did reveal the contents of the notes they received. All of them threatened death or kidnapping if the victim refused to pay the amount of money that was demanded. Every note was simply signed “The Gang.”
By this point, the Herald had determined that this was an extortion case and ruled out any other possibilities. But if that was the case, then who were the targets — and what did “The Gang” want?
Rumors continued to spread. People spoke of a few Proctor residents who had also received mysterious kidnapping notes. Soon, other so-called extortion letters were reportedly found. The authorities traced the letters to post offices in Fair Haven and Poultney. Federal agents now were spreading their investigations across Rutland County. Newspaper boys from across the county were also brought in for questioning, as the FBI worked to figure out whether the local newspapers were hiding some sort of coded message.
Meanwhile, in Brandon, George H. Young received a death threat instructing him to leave a specific amount of money at a chosen location at Neshobe Country Club. George contacted the police who sent him to the country club to place a dummy package in the designated spot. It was never picked up.
Later, the investigation uncovered an abandoned camp in the woods near a green at the Neshobe Country Club. This secluded woodside perch provided an excellent view of the clubhouse and surrounding area.
Apparently, when George Young dropped off the dummy package at the golf course, the extortionists were observing him the entire time. When they gathered that police were involved, they decided not to retrieve the package.
Among the many who allegedly received kidnapping notes was Redfield Proctor Jr., a well-known local figure, who was formerly a Vermont governor and owner of the Vermont Marble Company. But the Proctor family denied such accusations. A plot against Proctor would have made sense; the well-respected businessman was incredibly wealthy and had great influence. Nevertheless, the Proctors remained silent.
Rutlanders and a gaining population of curious followers across the country were baffled. People wanted answers. Despite the massive scale of the investigation, no information was turning up and no answers were being given — at least to the public.
Undeterred, the Herald continued to seek answers. The paper sent a telegram to the FBI offices in Washington demanding an explanation. The reply was, not surprisingly, vague and didn’t yield any new information.
Instead, the Bureau accused the Herald of exaggerating the story, and attempted to diminish the scope of the investigation by asserting they had only sent 12 agents as opposed to the actual 20 who were currently in the city. The Herald would later print the FBI’s reply.
And then there were none
Just as mysteriously as the mysterious occurrences in the spring of 1934 started, they seemed to stop. Though the FBI held Rutland in gripping tension for two months, the Herald never reported any arrests or any breaks in the case. By May, stories about “The Pine Hill Mystery” seemed to fade.
Then on May 25, four men were reported driving around the town of Proctor for several days in a car with New Hampshire plates. Witnesses also reported seeing a machine gun within the car. But the car and its occupants seemed to simply disappear — as did the federal agents.
After two intense months of shocking encounters and gripping newspaper headlines, the Herald stopped reporting on “The Pine Hill Mystery.”
Now, we are left to ask what happened. Why did the FBI come to Rutland? Was there actually an extortion case? If so, who was the target, and was it ever solved? Or was this a coverup for something far more sinister?
Despite the case running cold, there is an interesting footnote to the story. Years later, former Herald editor Kendall Wild reached out to his high school classmate, Sam Willson, for some answers. Earl V.K. Willson, Sam’s father, was a successful Rutland businessman, who, at one time, lived with his family in the mansion at 1 Shadow Lane in Rutland.
According to Willson, his family was allegedly one of the targets of the extortionists. But his father never spoke a word of it. It was their mother who, decades later, finally told her children about it.
At time, Willson assumed his mother was making it all up until Wild contacted him. Amused, if not a little taken back, Willson was now able to recall some peculiar events from his childhood that suddenly took on another meaning to him. He remembered his parents buying a German shepherd for him, to keep him company. In hindsight, the dog was a likely protector more than companion.
His parents also hired a nanny for him and his younger brother so there would always be an adult supervising them.
But the strangest thing he recalled was the big black sedan that parked for a time at the top of Shadow Lane, blocking the rear entrance of their driveway. Willson now believes his parents kept silent about the case because they didn’t want to scare them.
To this day, no one seems to have any answers, and the FBI isn’t talking. Rutland author Mary Fregosi, who first investigated this strange tale for the Rutland Historical Society in 2007, attempted to contact the FBI for some answers. Their reply stated that their records on this case were destroyed in 1998, leaving this great mystery just that.
So were any arrests ever made? And did the FBI find what they were looking for among Rutland’s residential neighborhoods and manicured golf links? We’ll most likely never know, making this startling mystery an eternal reminder of man’s fight against evil.
(Information for this story was gathered in part from the Rutland Historical Society Quarterly Vol. 38, No. 2, 2008, by Mary Fregosi.)
Pine Hill’s Strange Ruins
These rather cryptic and minimalist ruins sit squat and mute near a former quarry that digs up an entire hillside of the park, and are covered with an awesome array of grattfi art and graffiti vulgarity. The empty concrete shells are probably more interesting in their death as impromptu art installations than what they were originally perfunctorily constructed for. Back in the day, buy local wasn’t a slogan you saw on the bumper of the Subaru in front of you; it was cheaper, more convenient, and you most likely were getting good quality for your patronage.
In 1918, the Rutland Department of Public Works needed more rocks to satiate the growing city’s construction projects. People of the Marble City had loads of them in their back yards, but these collecting localities were finite resources, and the DPW began to grow tired of hauling their rock crusher around the city via a horse. So they settled on a permanent location – where UVM surveyors found a good reserve of Cambrian Quartzite – which was solid in nature and perfect for public works projects. By 1925, the new site with a rock crusher was constructed hastily in Pine Hill Park, but by 1932, a laundry list of opposition resulted in it’s closer; including the aforereferenced half-assed constriction, cheaper prices from other quarries for better quality, and an encroaching city with residents who complained that the rock crushing machines were too loud. The place was abandoned and more or less left as it was, minus the machinery and the innards.
Today, it’s a cool part of the park to wonder around if you’re into spray paint art, are a spray paint artist, or just like urban ruins. Pine Hill Park itself is worth the trek. With a lot of passionate hard work and community involvement, it’s worked its way as a venerated regional mountain bike trail destination.
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