Question: How does the "timeline loop" with the kid becoming the mob boss (and looking to kill Bruce Willis 30 years later) start? If it gets started by "old" Bruce Willis killing the kid's (future mob boss) mother, and getting him very angry and revengeful, because Willis wants to revenge the death of its wife by the future mob boss... Then it is a chicken and egg problem.
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Chosen answer: The first time the time-loop occurred it is not necessarily due to Bruce Willis' character killing her. She could have died in another way, instigating the timeline in which Bruce Willis is taken to close his loop. He knows who the rainmaker is and therefore attempts to kill him in order to preserve his happy future. This in turn creates a brand new timeline in which Joe kills himself to save Sara, who in turn prevents the rainmaker from becoming a crime lord.