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.

Lufthansa cargo terminal at JFK Airport.      
    

On December 11, 1978 half a dozen masked robbers raided the Lufthansa
Airlines cargo building at JFK Airport in New York, making off with more
than $5 million in cash ($21 million in today’s dollars) and almost $1
million in jewelry. To this day, the Lufthansa heist, as it is known, is
considered one of the greatest in U.S. history. The plan was dreamed
up by Peter Gruenewald, a Lufthansa cargo worker at JFK Airport. The 
heist was dramatized in the classic mafia film "Goodfellas."

A van used during Lufthansa Airlines robbery at JFK
International Airport.

Vincent Asaro, a member of the Bonanno crime family, allegedly
helped carry out the bold heist of cash and jewelry from a cargo
terminal at JFK airport.

1990

Black Bart (Charles Earl Boles)
(b. 1829; d. after February 28, 1888)

Authorities almost catch the California bandit and infamous
stagecoach robber called Black Bart; he manages to make
a quick getaway, but drops an incriminating clue that eventually
sends him to prison.

Black Bart was born probably in the state of New York around
1830. As a young man, he abandoned his family for the gold
fields of California, but he failed to strike it rich as a miner and
turned to a life of crime.

By the mid-1850s, stagecoaches and Wells Fargo wagons transported
much of the huge output of gold from California. Often traveling in
isolated areas, the Wells Fargo wagons and stagecoaches quickly
became favorite targets for bandits; over the course of about 15
years, the company lost more than $415,000 in gold to outlaw
robbers.

It is believed that Boles committed his first stagecoach robbery in
July 1875.