The game-winning hit was delivered by Tony Wolters, who had an RBI single in the 13th inning that scored Trevor Story.
Joe Maddon has enjoyed tremendous success in his four seasons as manager of the Chicago Cubs, but there has been some talk about his World Series championship and NL Manager of the Year Award not being enough for him to keep his job next year.
Shap's unique perspective being surrounded by Cubs fans for this big Rockies game was explored too.
"You're always wondering, 'How's this going to end?' But our guys fought all night and to be able to get that last out there was great", Oberg said.
"I don't know if there is anybody better in the big leagues in a situation like this", said Cubs infielder Daniel Murphy, who faced Lester in the 2015 playoffs with the Mets and the 2017 postseason with the Nationals. But Maddon will still be setting the lineup come spring training 2019.
The Rockies struck early by getting a run in the top of the first inning.
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As Arenado applied the tag in the middle of the base path between second and third, Baez wrapped his arms around him.
Lester helped Chicago stick around by matching a career playoff high with nine strikeouts in his 26th postseason appearance.
Charlie Blackmon led off with a five-pitch walk.
Gore instead faced a 3-2 count and struck out, and so did Baez and Almora, ending the game.
That one run looked as if it might hold up as Freeland cruised into the seventh. He ran for his star first baseman with the speedy Gore, who promptly swiped second.
To put it mildly, the odds were heavily stacked against the Colorado crew, which was forced by Major League Baseball's insanely compressed post-season schedule to travel to two time zones in two days to try and take down legacy squads on their iconic home fields.