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The origins of the caboose appear to date back to the 1840s when Nat Williams, a conductor of the Auburn & Syracuse Railroad (a later affiliate of the New York Central).
He became fed up with cramped and uncomfortable quarters to do paperwork (a common job of the conductor, whose responsibility is general oversight and control of a train, passenger or freight). This was usually done within either a free space on a passenger car or combine/baggage car.
To fix this
problem, Williams found an unused boxcar and, using a simple box and
barrel as a seat and desk, set up shop to do his duties. Not only did he
find there was plenty of room to work but also figured he could use the
unused space to store tools (flags, lanterns, spare parts, etc.) and
other essentials when needed.