3 reasons the Chicago Cubs will win the 2024 World Series and 2 reasons they won't

The Chicago Cubs will not win the 2024 World Series because the rotation has too many question marks

The Cubs' projected Opening Day starting rotation is awfully lefty heavy. It features three lefties while most teams utilize just one or two, and if there’s an injury to one of the righties the next man up is likely a lefty as well.

Even if you remove the lack of balance from the equation and look at the rotation as individual players, there are more than a few question marks.

LHP Justin Steele had a great season in 2023. He’s improved steadily for several years and was a legitimate NL Cy Young candidate until a problematic September. The question has to be: which Steele are the Cubs getting in 2024? The Cy Young-caliber pitcher that was slotted in as the team's number two in the rotation behind Marcus Stroman? Or the guy that showed up in September and got rocked? How will his contract negotiations (or lack thereof) with a President of Baseball Operations that’s unwilling to compromise impact his play on the field as he enters 2024 making just $4 million dollars?

RHP Kyle Hendricks is another player that had as good of a 2023 as you could have possibly hoped for. Coming off of what could have been career-ending injuries he had a 1.5 WAR from Baseball Reference to go along with a 3.74 ERA and 3.81 FIP over 137 innings. Is that fair to expect again? In order for this team to be a World Series contender, those numbers are barely good enough coming from a number two in the rotation but anything worse won’t work. Can Hendricks stay healthy?

LHP Shota Imanaga was a splashy signing. However, he’s 30 years old and he’ll be adjusting to playing in a foreign country and all of the challenges that come with that. Moving to a new place, talking to new teammates (especially when you are learning the language), and adjusting to an entirely new league is difficult. Daisuke Matsuzaka had a 2.90 ERA and an 18-3 record in his second season in Boston. However, in his first season, he had a 4.40 ERA. Yu Darvish had a 2.83 ERA in his second season with the Texas Rangers, but he had a 3.90 ERA in his first season. Pitching in this league is not easy and it’s certainly not easy as a rookie. Can Imanaga come in and not look like a rookie?  

RHP Jameson Taillon was the opposite of Steele and Hendricks. If we’re going to look for a player that can improve on his 2023 Taillon is the one to look at. Last season, the former first-rounder had the highest ERA of his career and his highest HR/9. His ERA was almost a full run higher (4.84) than his career average (4.00). Taillon was signed through Hoyer’s patented “intelligent spending,” and that signing has not paid off. Can Taillon regain his form and be a pitcher that the Cubs can depend on in 2024?

LHP Jordan Wicks was a nice story to end the season, but his promotion raises questions that can’t be answered until this year. While Wicks was having a nice season, the prospect on every Cubs fan’s mind was Ben Brown. After a scorching start Brown slowed down, as prospects often do, and he was passed up by Wicks. While Wicks has a level of consistency that keeps his floor very high, he will still be a rookie in 2024 and any time a rotation features two of those going into opening day it has to give you pause. These questions don’t disappear if it’s Brown or even Cade Horton in the rotation to start the season, and you just have to wonder if the Cubs are putting too much pressure on these starters in a way that could potentially stunt their development.