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Year In Review — The Reporter goes to jail

This story was published in July 2023.

Although the headline above might bring joy to a few readers of this newspaper, it’s not what you think. We went to show you a place very few Islanders have ever seen. And those few who have, well, let’s just say they’re usually a bit reluctant to talk about the experience.

And so, with the accuracy police blotter reports strive for: On Thursday, June 20, at 1 p.m., the Reporter went to jail in the basement of the Shelter Island Police Department headquarters.

On duty was Sgt. Anthony Rando, who has been a member of the Department for 13 years. Promoted to the rank of sergeant in 2022, means he spends more time at headquarters than in the past, which also means more time dealing with the jail.

Before a tour of the present jail, a little history is in order. “Little” should be taken literally, since the history of the Shelter Island jail is not well documented and doesn’t give up its secrets easily. The Shelter Island Historical Society could only come up with one reference, and that was from 1922, and it wasn’t about a jail, but a lack of one.

From an unidentified newspaper, an item appeared with a dateline “Shelter Island, N.Y., Sept. 18: “This town, small of area but large in virtue, with no poor in the alms house and no children as county charges, finds a burglary so unusual that … Justices of the Peace did not know exactly what to do with the case. And after three Justices had conferred on the alleged crime they sent to Riverhead for assistance.”

By the late 1930s, the rare miscreant was spared a ferry ride in shackles and could bed down behind bars on the Island.

Overnight accommodations used to take place in a cell in the basement of the old Town Hall. Where police headquarters is today once housed offices of the Town Supervisor, Town Clerk, and Tax Assessor, with the Police Department operating out of the basement of the Depression-era building.

This arrangement remained until 1999, when Town Hall moved to its current location and the Police Department took over the building.

Up to date in the slammer

Today, one room of the jail complex is lined with desks, drawers, paperwork, and technological equipment. On one side of this room stands a desktop where arrested suspects have all of their information entered into the police database. This includes details of the crime that the officers present, as well as the suspect’s mugshot and fingerprint scans, both of which are taken on-site.

Only two cells in the Shelter Island jail. (Credit: David Brush)

The fingerprint scanner is a device resembling a small printer. It’s completely digitized and scans fingerprints without the use of ink. It then sends the prints to the database and uses them to see if the suspect has committed any past crimes.

The mugshot camera is an upside-down Canon mounted to the wall above the desktop. It’s flanked by two light strips, and faces a blank wall as well as two footprint markings on the floor where subjects are asked to stand.

Asked about height markings and an identity placard across the chest, Sgt. Rando smiled, saying those days are gone. Because everything is digital, mugshot photos are now automatically linked to database records concerning physical information on the suspect.

To the right of the mugshot zone stands another desk, holding a large gray machine called the Intoxilyzer 9000. This is used for incidents where people are arrested and suspected of driving while intoxicated. According to Sgt. Rando, this is the most common crime that warrants an overnight stay, because the court will not arraign people who are under the influence of alcohol or drugs.

The Intoxilyzer 9000 differs from a breathalyzer in the sense that it is more accurate, and, of course, has a much cooler name. “Breathalyzers are basically pass/fail” Sgt. Rando said, explaining that breathalyzers are primarily good for distinguishing intoxication from the use of other drugs, or various medical issues.

Once a person is accused of driving under the influence of alcohol, the Intoxilyzer will give a much more specific reading of blood alcohol content for use as evidence.

The Intoxilyzer works by initially cleaning itself with air blasts through its connecting tube. From here, it heats up the tube to prevent condensation from forming, at which point Sgt. Rando or another officer will place a single-use mouthpiece on it. Individuals are then asked to blow forcefully and steadily through the tube, allowing the Intoxilyzer to determine the true amount of alcohol in their bloodstream.

On the left side of the room is a smaller space marked by a chair, handcuffs that are connected to a desk, and a clear plastic wall with holes in it that allows sound to travel through. This is where suspects sit across from an officer and take part in a physical and mental evaluation.

The spot where suspects are questioned, and important data recorded. (Credit: David Brush)

Interpreters are also on hand to defuse any confusion over language. They are able to explain on the officer’s behalf why the suspect has been arrested, what their rights are and what’s going to happen next. Additionally, officers write down the suspects medicinal needs and evaluate them for the possibility of a suicide watch.

Finally, any property beyond essential clothing is taken, such as belts, shoelaces, keys and phones. This property is recorded before being placed in a bag that only is returned to the suspect once their time in jail comes to an end.


Because there is so much information to process, it takes a long time for those arrested to even make it behind bars. “Typically, an arrest can take four or five hours to process,” Sgt. Rando said.

He added that officers must realize the anxiety that this procedure can cause. “I always try to keep people aware of what the next step is,” he said, noting that respect is a two-way street. “When people comply with us, that’s the biggest thing,” he said. He strives to “do the right thing by people,” and finds peace in the fact that most arrested individuals express gratitude in return, despite their predicament.

Locked Up

Once the forms have been completed, suspected individuals are released from their handcuffs and guided into a connecting room that contains two cells. The door to this room is made of black iron bars, which also cover two translucent windows. An air vent, a camera, and a voice monitor are mounted to the wall facing the cells, so that those jailed can be monitored at all times.

A bench, a sink and a toilet. (Credit: David Brush)

Each cell has one entrance/exit in the form of a sliding door made of white iron bars. Inside each cell is a long wooden bench, which doubles as a bed, in addition to a sink and a toilet, all of which are visible from outside the cell.

The incarcerated are given three meals a day, which can consist of sandwiches, burgers, and pizza from the IGA and local restaurants. Officers perform check-ins every 15 minutes to make sure the suspects remain in a healthy physical and mental state.

“We don’t want to hold anyone longer than we have to,” said Sgt. Rando, explaining that nobody has been held on Shelter Island for more than 24 hours. Whenever possible, he said, people are released on either a field or desk appearance ticket, at which point they’re free until arraignment. This has become more common in recent years, since the 2019 New York State bail reforms effectively eliminated cash bail.

“Our job is not to punish,” said Sgt. Rando. “It’s to safely get people to court.”

The purpose of the police force, he added, is “to keep our community safe, and make a positive impact on Shelter Island. I can count on one hand the number of times that people gave us a hard time.”

Asked about the  difficulty of being a police officer in a small town, dealing with people you grew up with, or members of families that you know, Sgt. Rando said that although that’s a common occurrence, biased treatment is not part of his playbook. “If you’ve known someone for 30 years, or are just meeting them today, treating everybody fairly and with respect is the most important thing,” he said.