It's the first time the organization has gone to the playoffs for three straight seasons since 1906-08, per ESPN Stats and Info.
The 2017 season hasn't gone quite according to plan for the defending World Series champions. After winning 103 regular-season games and ending their 108-year title drought in 2016, the Cubs returned all of their key players and appeared poised to maintain their place atop baseball.
"If there's a reason to be concerned about the 2017 Cubs, it's that they don't have much depth underneath a starting rotation that was worked hard last season," he wrote. "But like with the [Cleveland] Indians, the names in said starting rotation are too good for doubts to rule the day."
The Cubs haven't dealt with a significant number of injuries to their starting rotation, but the respective workloads of Jon Lester, Jake Arrieta and Kyle Hendricks may have played a part in the trio taking a step backward from 2016 to 2017.
In 2016, Cubs starters collectively ranked fifth in FIP (3.77), third in strikeouts per nine innings (8.88) and 15th in walks per nine innings (3.05), according to FanGraphs. This year, Cubs starters are 12th (4.34), ninth (8.25) and 10th (2.99) in those three categories, respectively.
Chicago's rotation remains solid, and Jose Quintana has been as good as advertised after the team acquired him in July. The southpaw has gone 7-3 with a 3.50 ERA in his 13 starts with the team since arriving from the Chicago White Sox.
Still, the margins for error become much smaller in the postseason. When the Los Angeles Dodgers rotation goes six-deep and the Washington Nationals boast the trio of Max Scherzer, Stephen Strasburg and Gio Gonzalez, the road to the World Series could be treacherous for the Cubs.
History isn't on Chicago's side either. In the last three decades, only two MLB teams have successfully defended their title. The Toronto Blue Jays went back-to-back in 1992 and 1993, and the New York Yankees won three World Series in a row between 1998 and 2000.
Of course, nobody would consider the Cubs underdogs in the postseason. Hendricks and Lester were instrumental in winning the Fall Classic a year ago, and Kris Bryant and Anthony Rizzo anchor a dangerous offense.
FanGraphs give the Cubs an 12 percent chance of winning the World Series, which is second-best in the National League. FiveThirtyEight, meanwhile, lists the Cubs behind the Dodgers and Nationals with a 10 percent chance of winning a title.
Few would be surprised if Chicago brings home its fourth World Series title in franchise history. By the same token, the discussion of the Cubs as the next great MLB dynasty may have to be put on hold until 2018 depending on how the 2017 postseason shakes out.