On July 29, 1928, Herbert R. Mackie, an inmate at what was then known as Clinton Prison (today called the Clinton Correctional Facility) in Dannemora was being escorted to a practice session for the prison’s band. He told an officer that he had forgotten something, and asked for permission to return to his cell. He was not seen again by prison staff for six weeks.

He was not at liberty during most of that time, however. He was still within the facility, busily digging a tunnel that would be a key part in what seems to have been a carefully planned plot for Mackie to escape the prison with fellow inmate Otto Sanford.

The band had their session – a rehearsal for a performance they would give before a ball game later that day. Mackie, who played cornet, was not missed – not a great testimonial to his ability.  It wasn’t until a roll call after the rehearsal that Mackie’s disappearance was first noticed.

Given that it was daylight when Mackie “left” and that the walls were manned (making it nearly impossible for him to have gotten over the walls unnoticed), and the fact that it had been years since any “over the wall” escape attempts had been made, the authorities at the prison strongly believed that Mackie was merely hiding out somewhere within the institution.

A systematic search was begun, which involved workers “ripping out floors and partitions of the factories and tearing down any walls which may afford a hiding place” according to the Brooklyn Standard Union. The Saratogian noted that “For weeks after Mackie’s disappearance prison officials tore up floors in a vain attempt to find him.”

Despite these efforts, Mackie simply could not be found. He was diminutive – some newspapers described him as “the midget bandit of Brooklyn” (Actually he was not that small: even the Brooklyn Daily Eagle, which termed him a “midget” several times, once noted that he was “slightly taller than a midget,” the Standard Union gave his height as 5 foot, 5 inches, and his 1917 draft record said he was of medium height). Due to his size, there were surely a number of small places where he could have secreted himself.

Born in Morrisville, Madison County in 1898, Mackie’s parents (Edward and Henrietta) lived in the town of Marshall in Oneida County for a while. Property they had owned there was sold at a foreclosure auction, and the family relocated to Brooklyn, where in 1905 Edward was working as a house painter.

Young Herbert was into trouble early on. By 1910 he was a resident of the State Juvenile Asylum and Children’s Village in Westchester County. Years later, it was reported that “as a boy [he] was described as ‘too tough’ for the New York Juvenile Asylum.” By 1917, he was working as a chauffeur in Brooklyn, was married, and had a daughter.

Herbert Mackie was arrested in 1924, one of several men accused of holding-up drug stores and groceries in the New York City area. The city’s police department, in its 1924 report, mentioned his participation in these crimes, and also said that he had fired several shots at a policeman during one robbery, and was known to carry a sawed-off shotgun. Though it was later said that he’d admitted to having been involved in about 50 holdups, he seems to have been convicted of only one. He was sentenced in March 1924, and sent to Sing Sing, where he was received on March 27, 1924. His intake information there states that his robbery conviction was a first offense, and that his occupation was “Musician and Barber.” He was sentenced to 20 years, and would not be eligible for parole until 1934.

At some point Mackie was transferred to Dannemora. Perhaps because he had some experience as a musician, he joined the prison’s band – which entitled inmates to some special privileges. In time, he became acquainted with another inmate musician, Otto Sanford. Sanford had been born in Germany in 1892, and came to the United States in 1914. (Years later, it was reported that he had been the band leader on the German liner, S. S. Vaterland – this ship’s operations were complicated by the First World War, and it was eventually seized by the United States and renamed the Leviathan).

After being in the U. S. a short while, Otto Sanford was convicted of having stolen $80, and was sent to a New Jersey reformatory for 18 months. Later, Sanford served several years in Connecticut for having stolen a car, and was also convicted in Massachusetts for possession of burglary tools (which he claimed were merely a screwdriver and pliers that he used to repair musical instruments). On learning that he was to be deported, he determined to take his son back to Germany with him. Having no funds to accomplish this, he stole some money and it was this crime which landed him in Dannemora. Sanford’s prison record says he was a musician (and also shows that he claimed to be innocent of the robbery charge). At Clinton Prison, where Otto Sanford worked as a weaver, he was also a member of the band.

Prison band-mates Mackie and Sanford formulated a plot. They would dig a tunnel leading from the floor of Sanford’s cell into the sewer system. From there a manhole provided access to the prison yard. Reaching the yard was only the first step – the walls would still have to be surmounted. (This was prior to the construction of the present wall, which was built up during the 1930s–the walls that existed in 1928 were by no means as formidable as the one that exists today.) Apparently a rope would be used to scale the wall.

Probably because of his slight build, Mackie did the tunneling. Presumably, they had already gotten the tunnel started when Mackie skipped out on band practice and he had enough space under Sanford’s cell to conceal himself initially. Once down there, he used some pieces of steel as digging tools. As his work progressed, he enjoyed certain comforts: he had a mattress to sleep on, cigarettes, an electric light that was powered by current from the prison’s electrical system, and even had an improvised hot plate to heat his food. He began the project with a supply of food he’d squirreled away, which was supplemented by Sanford after his initial rations ran out.

Mackie burrowed away for weeks, undetected by prison staff. Finally, the tunnel was large enough so that Sanford could also use it. In early September – about six weeks after Mackie’s disappearance from the band – both men slipped out into the prison yard. Soon after, prison officers found a rope near the wall not far from the warden’s quarters.

Mackie’s and Sanford’s freedom was short-lived. Both were apprehended during the night of September 7th, a few miles away in the Picketts Corners area. An officer from the prison spotted Herbert Mackie and fired at him, but a local farmer, Eli Gonyea, was credited by newspapers as the one who actually caught him. Otto Sanford was spotted in a field near Picketts Corners, and was soon surrounded and taken back into custody.

Four prison officers were suspended as a result of the escape (at least two were dismissed), and Mackie and Sanford were tried in Clinton County on escape charges. Remarkably, they were just two of the four inmates who escaped during the summer of 1928, leading to what the Plattsburgh Sentinel called “Convict Week” at the courthouse. That fall, in addition to Mackie and Sanford, Charles Chukes (a trusty who had run away from the prison farm) and William Little (who used a rope to go over the wall, apparently in an escape not connected with that of Mackie and Sanford) were also put on trial and found guilty.

Mackie requested a jury trial, and testified on his own behalf. The Plattsburgh Sentinel reported that he “proved to be a very poor witness.” The jury was sent out for a dinner break, and when they returned, Mackie changed his plea to guilty. As a previous offender, he was sentenced to serve an additional 14 years, the maximum he could have received under the provisions of the Baumes Law (an anti-recidivism act passed in 1926 through the efforts of State Senator Caleb H. Baumes). Sanford, a multiple offender, was tried and given an automatic life sentence, as stipulated by the Baumes Law for anyone who had been convicted of three felonies (whether in or outside New York State).

Despite Mackie’s sentence, he somehow regained his liberty before serving all the time he’d been sentenced to. The 1940 Census listed him in the Brooklyn household of his brother, Walter G. Mackie, and Herbert was employed as a longshoreman. That same year, however, he was arrested in connection with the robbery of a used car salesman. Mackie was locked-up in Brooklyn’s Raymond Street jail and was found dead in his cell early in September 1940 – almost exactly 12 years after he had topped the wall at Dannemora. It was determined that he died of natural causes.

As for Sanford, the 1930 Census listed him among the inmates at Clinton Prison, but he was transferred to Auburn, where he became the musical director of the prison’s band and orchestra. In 1937, he was one of several convicts whose sentences were commuted by Gov. Herbert H. Lehman, making it possible for him to be deported to his native Germany.

In the year following the escape of Mackie and Sanford, inmates at Clinton rioted and significant damage was done to the facility. It was during its reconstruction that the wall was heightened and strengthened. Walkways along the tops of the walls were removed, and the observation towers were enhanced, leading to the foreboding structure shown so frequently during television coverage of the 2015 escape by Richard Matt and David Sweat.

Illustrations, from above: The Clinton Prison before the walls were raised; the San Quentin inmate band in a photo taken at about the time of Dannemora escape; and newspaper headlines.