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How do the Cubs get to the next level of contention?

As the ball landed, an era ended. Anyone watching dispassionately probably knew it. As Kyle Schwarber's ball landed in the Allegheny River after a Gerrit Cole pitch the Pirates were rebuild-bound. Unable to afford free-agents to fill their comparative weaknesses, it became very bleak for Pittsburgh. Are the Cubs to the point where they can largely avoid the boom/bust cycle?

The Los Angeles Dodgers have won seven NL West crowns in succession. They’ve clinched a postseason spot and figure to win the 2020 division title as well. Nobody seems to be asking when the Dodgers’ window of contention will be over.