I wondered about these train crossing watchmen and then came across this explanation in the The Gleaner from Wed, Apr 10, 1895.

ANSWERING A QUESTION,
Councilman Johnson asked a question at last night’s council meeting. It was: “If a watchman is needed at the Green street crossing of the L. & N. railroad, why not at the Elm street crossing also?”
If Mr. Johnson, at 8 o’clock this morning, will walk from his place of business to the crossing in question and remain there until 9, if he will repeat the action for an hour and a half, beginning at 12 o’clock noon, and again from 3 to 4:30 o’clock this afternoon, his question will be fully and finally answered. It is the daily practice of the L. & N. railroad to stop long south-bound trains at its Henderson station. When the engines attached to these trains are at the station, the rear cars are strung across Green street. Then more than at any other time is the danger apparent.
Frequently the crossing is blocked just at the hours when children are coming from or going to the Seventh street school.
Instead of waiting until the way is cleared they run under or over the cars. Every time this happens, and the occurrence is a most common one, a life is jeopardized. With a watchman and gates, no one could be injured. Will the council wait until somebody’s child is killed and a judgment secured against the city for heavy damages? Will the city fathers put themselves on record as saying the life of a child is worth less than a watchman’s salary? A chance will be given to make such a record at the next council meeting.
Station a watchman at that Green street crossing.