Complex sentence: On the afternoon of June 9,1930, in Chicago, Jake Lingle left the Sherman House Hotel, where he had conversed with some power brokers, to catch the 1:30 pm train to a racetrack in Homewood where he gambled on horses.
Split into simpler sentences: On the afternoon of June 9,1930, in Chicago, Jake Lingle left the Sherman House Hotel where he had conversed with some power brokers. Lingle was on his way to catch the 1:30 pm train to a racetrack in Homewood where he gambled on horses.