A Killing on Fishkill Mountain

When the law finally caught up with William “Big Bad Bill” Monroe, his criminal record spanned over several decades. His first reported crime, in 1903, was when he was charged with burglary in Plattekill, New York in Ulster County. As time went on, Monroe’s crimes became increasingly violent. This especially held true when he consumed too much alcohol. 

Monroe stood at 5’8” and weighed roughly 170 pounds. He had cold blue eyes and sandy colored hair. Some reports stated that his face was very weathered face with high cheek bones and that he spoke with a “hills folk accent.” Monroe made national news headlines from his spectacular assault of the entire Deyo Family of Gardiner, New York, and a subsequent manhunt which ended upon his capture in California. The then District Attorney for Dutchess County in New York wrote that Monroe had “a very bad reputation, and was a terror to the residents of Dutchess County, in the vicinity of which he lived while he was here, and for several years while a resident of Ulster and Orange Counties, he more or less terrorized the farmers in those counties so that they were in mortal fear of him at all times.” 

In the summer of 1922, Monroe was released from Dannemora Prison in Dannemora, New York (also known as the Clinton Correctional Facility). Prior to that, in an Orange County, New York courtroom, he received a sentence of three years of internment for a burglary he performed in Cornwall, New York. “Big Bad Bill” spent those three years in Sing-Sing Prison in Ossining, New York. He was eventually sent to Auburn Correctional Facility in Auburn, New York where he escaped from a chain-gang, only to be recaptured and returned to the facility. Once he finished that sentence, he was back at Dannemora and was finally paroled on June 15, 1922. 

During this time, Monroe was a hardened criminal at only forty-four years of age. It took Monroe a mere six months to recommence troublesome acts. In August 1922, he was arrested in Gardiner, where he was known as “The Gardiner Desperado”, for stealing a gun, a coat, a pair of shoes, and a straw hat. The case was dismissed.

After being released from prison, Monroe worked odd jobsin order to secure some extra cash, including obtaining that security via extra legal means. He knew that his brother-in-law,Andrew Barrett, who lived in a cabin on Fishkill Mountain, was affluent. In fact, his seventeen year old nephew, Harold Barrett, affirmed that many valuables were hidden at this cabin. The pairdecided to make the journey to the cabin in search of wealth, as they had recently been stranded in Sloatsburg in Rockland County, New York because the Ford that they used for transportation had broken an axle and Monroe could not afford to fix it.

Seemingly, there was nothing out-of- the-ordinary when Monroe and his nephew arrived at Fishkill Mountain in late July 1923. The two men “lived in the vicinity of Andrew Barrett.” They were frequently seen visiting the area; sometimes separately, sometimes together. 

On the afternoon of July 23, 1923, Harold Barrett acted as a lookout as Monroe entered the cabin. A fight broke out; an autopsy later revealed that Andrew Barrett suffered from a shattered jaw and a fractured skull. The fatal blow resulted from an axe which Monroe brutally used to sever off half of his brother-in-law’s head. While Andrew Barrett lay dying, Monroe and Harold Barrett tied him up with linens and searched the cabin. They found several thousand dollars in cash and fled.

The body of Andrew Barrett, who was also known as “The Fishkill Hermit,” was discovered a few days later by neighbors who periodically bought milk from him. They witnessed a “heap [of] bedclothing, mattresses, chairs, and rubbish of all sorts, and in poking about this bunch of rubbish, they uncovered a foot….” It appeared as if Andrew Barrett had been hogtied, as “some rags were tied tightly around his throat, his eyes protruding from the sockets, and on top of his head was a hole the size of a rifle barrel, completely through his skull…” They called the New York State Police. 

Monroe became a prime suspect. A warrant was issued for his arrest on July 30, 1923. Law enforcement officials focused their search in Sullivan County, New York, as Monroe was known to frequently hideout in the mountains there. It was believed that Monroe and his nephew bolted in “a Ford” automobile and proceeded to cross the New York state line into New Jersey.

After Sullivan County, the focus of the manhunt for the killer and his accomplice switched to Suffern, New York where Harold Barrett’s mother lived. Suffern Police Chief Lunny and New York State Police Sargent Flynn, Undersheriff C. Fred Close, and Corporal Buckly staked out the area around the woman’s house. A break in the case came when Harold Bennet’s mother went to the post office to mail a letter addressed to the fugitives. It was addressed to Pomfort, New Jersey. 

The law enforcement team followed this lead when Lunny, who knew Monroe, saw him walking along the road near Sussex, New Jersey in Boonton. The police chief jumped out of his vehicle and knocked Monroe to the ground with one blow. He then quickly cuffed him. 

Harold Barrett was discovered staying in a house in town. He too was arrested. On August 1, 1923, the two criminals were placed in the Dutchess County Jail. Two days later, Monroe initially pleaded not-guilty. However, he then waived his right to an examination. One newspaper wrote that perhaps with fifty witnesses, the prosecution had been enough to convince Monroe that he would most certainly be executed for his crimes.

After a short discussion with W. Harry Montgomery, Monroe’s court-appointed lawyer, Monroe changed his plea to guilty. He was sentenced on October 30, 1923, to twenty yearsto life for second-degree murder. Once again, Monroe would serve his time in Sing-Sing before being transferred several times. Harold Barrett’s lawyer moved for a dismissal of the charges against his client; he would end up being re-arrested for burglary and larceny in December 1924. 

In a bizarre twist to the story, shortly after his sentence commenced, Monroe sent a letter to the District Attorney of Dutchess County proclaiming his innocence on November 7, 1923. He also offered to shed light on who actually killed Andrew Barrett; he claimed that person to be Edward Conney.Monroe stated, according to The New York Times, that he had a signed confession from Conney which had been obtained by friends who wanted to help him. 

William H. Anderson, the former State Superintendent of the Anti-Saloon League (an anti-Prohibition organization), met Monroe when he was in prison for forgery. Anderson felt assured, per his frequent conversations with Monroe, that he wasnot guilty. The reason that Monroe ended up pleading guilty was because he did not believe that he could obtain a fair trial in Dutchess County. Shortly after his conviction, Monroe then claimed that Harold Barrett killed Andrew Barrett. This claimwas refused. 

Anderson petitioned Governor Al Smith regarding Monroe’s supposed innocence on December 31, 1927. The Kingston Daily Freeman reported that the governor called theDutchess County District Attorney for advice. The District Attorney reportedly told Smith that it was of his opinion that Monroe was a horrible individual and was where he should be -in prison. 

A few years after being sentenced, Monroe was transferred to Great Meadow Prison in Comstock, New York where he worked in the bake shop and did hall work. He was then movedfrom Great Meadows to The Institution for Male Delinquents in Napanoch, New York in Ulster County. It was a facility for people who were deemed to be criminally insane. He was admitted on September 11, 1934.

Captain John L. Hoffman, Acting Superintendent at the Napanoch institution, received a letter from the psychiatrist and psychologist who examined Monroe, prisoner #3145; they recommended that he be sent back to prison. In this letter, written on December 15, 1934, they concluded that they are “…not impressed that he is mentally deficient.” The Dutchess County District Attorney also did not believe that Monroe was criminally insane. During this same time period, he penned the following in a letter addressed to the Napanoch institution: “Under no circumstances should Monroe be paroled and I personally would do anything that I could to prevent any parole in this case.”

Although the antics of “Big Bad Bill” Monroe were closely followed during his two decade reign of terror, citizens of Ulster, Orange and Dutchess Counties exhaled a sigh of relief when the “Gardiner Desperado” had been locked up for a long time. Twenty-seven years after he was sentenced for the killing of Andrew Barrett, Monroe was finally due to be granted parole.During the summer of 1950, newspapers reported that he was allowed to go free – he was in his seventies at the time. After his release, Monroe mysteriously disappeared from the public record.

Photo Credit: NYSA The Institution for Male Delinquents in Napanoch, New York 1920. How Monroe would have seen it.