In recent years, the Chicago Cubs have struggled to light that postseason fire that drove the team deep into October for several years. From situations like scratching through a tough NLDS against Bryce Harper and the Washington Nationals in 2017 and losing the NL Wild Card game a year later, to missing the postseason completely in 2019, it looks like the Cubs have their work cut out for them. New Cubs skipper David Ross, may very well find himself on the wrong end of a potential World Series window.
Even with Ross at the helm, questions still loom whether or not this first-timer has what it takes to lead the team he played for during their 2016 World Series run back to the promised land.