Complex sentence: He went to work, spent the rest of the day with co-workers James McKeon and Timothy Girard, then took off McKeon's gun, tied up the pair and put $7 million dollars in the trunk of a car, then leaving with the money.
Split into simpler sentences: He went to work, and spent the rest of the day with co-workers James McKeon and Timothy Girard. He put $7 million dollars in the trunk of a car, then left with the money.