No time to read? Listen to the podcast.

For 55 years, from 1951 to 2006, nighttime to dawn riders of the New York City subway hardly knew what was happening right in front of their eyes. Few, if any, paid any attention to the two-car work train rumbling through their station or passing them on another track.

It was called the Money Train.

“The Board of Transportation*, as it was known at the time, converted about twenty R21- and R22-style cars into money train cars,” Jodi Shapiro told me. She’s the associate curator for the New York Transit Museum, located about 20 feet under Brooklyn.

“The cars were armor plated and had bars on the windows. The trains were staffed with about 12 collection agents, a supervisor and armed guards. Everyone wore body armor and everyone was armed,” she said. The trains were rolling fortresses.

Six nights a week, usually from 2am to 4am, the modern-day Money Trains traveled the rails, picking up cash, coins, and tokens from each station in the system. Most New Yorkers, myself included, never knew of its existence. After all, the trains carried tens of thousands of dollars in cash. It wasn’t the kind of story you wanted splashed across the cover of Time magazine.

At the end of their nightly runs, the Money Trains stopped under 370 Jay Street, roughly the location of today’s Jay St.-Metrotech station in Brooklyn (although through much of the Money Train era Jay St.-Metrotech was three separate stations). The location was chosen because it was situated over an area where tunnels from all three original subway companies—the IND, IRT, and BMT— passed close to each other. Armed guards would carry bags of money through a heavy metal roll-down crash gate, up four flights of stairs and into an elevator that took them to the second floor count room.

If the Money Trains were rolling fortresses the count room was a fortress on steroids. “You had to be buzzed in,” Shapiro said. “All the guards at the entrance were there twenty-four-seven. Inside the count room there were more guards, in bulletproof cages, carrying rifles. The people who counted the money had to wear special jump suits that had no zippers. They had to carry their lunches in clear, plastic bags. The Transit Authority was really serious about not losing revenue.”

Outside of some misplaced bills or change, no revenue was ever lost from the money room.

Except once.

“On Monday, July 23, 1979 two supervisors, Benjamin Williams and John Kenny, came into work and realized that something was amiss,” Shapiro said. Amiss? More like a’missing. Somehow, $600,000 in $10 bills had vanished from one of the safes.

I had to ask. How does a stack of money the size of a window air conditioner and the weight of an irish wolfhound disappear from a locked room? And not just any locked room. From the gold standard of locked rooms.

“The weekend that this money went missing,” Shapiro said, “there had been a planned blackout that silenced the building’s alarm system.”

That’s the weekend what came to be known as the Hole-in-the-Wall Gang struck.

“A couple of months earlier, two guards went on a coffee break together and accidentally locked themselves out of the money room. So they tried to figure out a way to get back in without letting anybody know,” Shapiro said.

The pair discovered there was a hole between the women’s locker room and the count room, that was secured by a loose metal panel. Although they reported it to their supervisors, the hole was never fixed.

It apparently became a turnstile to a $600,000 pay day.

“It smelled like an inside job,” according to Shapiro, “because the count room safes required two combinations to open, and the supervisors who were in charge only knew one combination each.”

After fingerprinting, interviewing, and administering lie detector tests to over 700 people, investigators were never able to prove who did it.

To this day, the money and the perpetrators—it seems reasonable to assume there were at least two people involved—have never been found. In 2015, the Transit Authority closed the 370 Jay Street facility and sold the building to New York University for a dollar (although $600,000 would have still been below market and would have at least let the Transit Authority come out whole). The secrets of the crime will be lost to laboratories and classrooms.

“Were the thieves opportunistic because they knew there was going to be an outage? Or was this something they had planned for years and years and years and happened to pick the best day ever to rob the count room?” Shapiro wondered out loud.

Either that, or there’s a psychic in New York who’s worth every dollar she charges.