On October 6, 1866, the brothers John and Simeon Reno staged
the first train robbery in American history, making off with
$13,000 from an Ohio and Mississippi railroad train in Jackson
County, Indiana.

Of course, trains had been robbed before the Reno brothers’
holdup. But these previous crimes had all been burglaries of
stationary trains sitting in depots or freight yards.

Colt 45 the favorite gun of the train robbers.

         
SANDY KOZEL

On October 6, 1866, the brothers John and Simeon Reno staged the
first train robbery in American history, making off with $13,000 from
an Ohio and Mississippi railroad train in Jackson County, Indiana.

Of course, trains had been robbed before the Reno brothers’ holdup 
but, these previous crimes had all been burglaries of stationary
trains sitting in depots or freight yards.

On October 5, 1892, the famous Dalton Gang attempted the daring daylight robbery of two Coffeyville, Kansas, banks at the same time.

But if the gang members believed the sheer audacity of their plan
would bring them success, they were sadly mistaken. Instead, they
were nearly all killed by quick-acting townspeople.

For a year and a half, the Dalton Gang had terrorized the state of Oklahoma, mostly concentrating on train holdups. Though the
gang had more murders than loot to their credit, they had managed
to successfully evade the best efforts of Oklahoma law officers to
bring them to justice.

On January 17, 1950, 11 men steal more than $2 million ($29 million today) 
from the Brink’s Armored Car depot in Boston, Massachusetts. It was the
perfect crime—almost—as the culprits weren’t caught until January 1956,
just days before the statute of limitations for the theft expired.

The robbery’s mastermind was Anthony “Fats” Pino, a career criminal who recruited a group of 10 other men to stake out the depot for 18 months to
figure out when it held the most money. Pino’s men then managed to steal
plans for the depot’s alarm system, returning them before anyone noticed
they were gone.

Anthony “Fats” Pino.

The Brink’s building on Prince Street after the heist.

A detective examines the Brinks vault after the theft.

Burlap money bags recovered in a Boston junk yard from the
Brink’s robbery.