The Chicago Cubs made a lot of moves this offseason to back up their assertion of being “all in” when it comes to making the playoffs for the first time since the abbreviated 2020 season.
Their biggest move, of course, was trading for multi-tool all-star right fielder Kyle Tucker from the Houston Astros. They picked up closer Ryan Pressly in a separate trade with the Astros. They also acquired rehabbed lefty starter Matthew Boyd, a co-starting catcher in Carson Kelly, and several bullpen and infield pieces.
Chicago Cubs Missing One Key Ingredient?

As things stand right now, they are favored to win the NL Central division and expected to make their first deep-ish playoff run since 2017.
But they may be missing one key ingredient needed to go from postseason-likely to postseason-successful.
Alexander Patt of Cubbies Crib believes that missing piece of the puzzle is postseason experience, especially when it comes to the starting rotation.
Patt points out that neither of the team’s aces, Justin Steele and Shota Imanaga, have MLB playoff experience. James Taillon has just 4.1 career innings of after-regular season play. Newcomer Boyd will head into 2025 as the most experienced of the lot with 12 career playoff innings (11.1 coming last season with the Cleveland Guardians).
The Importance Of High-Stakes Experience

The lack of such high-stakes experience leaves some uncertainty when it comes to how well the all-important starting pitching corps handles the stress of postseason play when/if the Cubs make it there.
In Chicago’s 2016 World Series-winning team and the successful 2015 squad the year prior, playoff-seasoned veterans played key roles.
Per Patt:
“To put this in perspective, compare this to 2015-2016. When they rose to legitimacy in 2015, their key move was bringing in an all-time postseason great in Jon Lester who won two rings in Boston and boasted 84 career postseason innings pitched. Jason Hammel also had 15 innings under his belt entering 2015. Come 2016, they brought in John Lackey, who had 127.1 postseason innings, and like Lester, also won two World Series championships; he notably pitched in the World Series clinchers for both of them (2002 with the Angels and 2013 with the Red Sox). There was value in having “postseason masters” in the rotation during those runs.”
Cubs Front Office Sees It Too

The Cubs front office has, apparently, seen the need for veteran leadership with postseason experience and has added some in other spots this offseason. Justin Turner, Ryan Brasier, Kyle Tucker, and Ryan Pressly all have World Series rings. Utility man Jon Berti has postseason experience, as do incoming pitchers Matthew Boyd, Eli Morgan, and Caleb Thielbar.
However, except for Boyd, the starting rotation will be relative babes in the woods when it comes to postseason play.
But will that matter all that much?
Well, the Cubs won’t know until they know. Steele, Imanaga, and the rest of the rotation could very well prove themselves to be clutch playoff assets, leading the team to next-level success….or not.
It’s very possible that Chicago, if they are in the thick of a pennant race in the middle of the summer, could trade for a veteran starter who would bring added leadership and experience to that run for postseason glory.
As is always the case in baseball, time will reveal all.
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