Complex sentence: He stops for a large lady, whom he assists in boarding the car, & starts again before a male passenger can board: the gentleman chases the car, eventually catching up and winning a great deal of money upon dropping five cents.
Split into simpler sentences: He stops for a large lady, whom he assists in boarding the car, and starts again before a male passenger can board. The gentleman chases the car, eventually catching up and winning a great deal of money upon dropping five cents.