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

The Chicago Cubs barely missed the playoffs in 2023 after an unprecedented collapse down the stretch, and the team that took their wild card spot made it to the World Series.

So is this team good enough to make it to a World Series like the Arizona Diamondbacks did last year? Or better yet, are they good enough to actually win the World Series like the Texas Rangers, snapping one of the longest championship droughts in the game?

I’d argue yes… and no.

The Chicago Cubs will win the 2024 World Series because of the addition of manager Craig Counsell

Last season was a mess and that mess was predetermined when Jed Hoyer refused to spend on a bullpen while also having a manager that was unwilling to get creative with the relief arms at his disposal.

There hasn't been much of a change going into 2024 in terms of Hoyer’s willingness to spend on relievers. The Cubs have not signed a relief pitcher and they’ve watched Josh Hader, a player that Counsell knows well, sign with a smaller-market team on a multi-year deal, Aroldis Chapman sign with a division rival that is notoriously cheap and David Robertson sign a one-year deal with the reigning champs. 

Beyond not adding a reliever, the Cubs no longer have Michael Fulmer, Codi Heuer, Brandon Hughes or Shane Greene under contract for next season.

So what is the difference between this season and last season? 

The difference is Craig Counsell. 

Absolutely no hate to former manager David Ross, but he was the wrong manager for the way that Hoyer had constructed the team. If Hoyer is going to pinch pennies, right or wrong, we have to have a manager that is willing to think outside the box and find wins. 

Patrick Mooney recently wrote about Counsell over at the Athletic (subscription required), detailing a personal managerial philosophy centered around 'solving for wins' - a true small-market necessity rooted in his experience as a manager and player. Expect less bunting, playing the percentages and riding a bullpen hard under this new skipper.

It’s hard not to look at what Mooney had to say about him as an admonishment of David Ross in disguise as a compliment of Counsell. That being said, if you could look to one area the Cubs could have improved in and made the playoffs last season it would be either through bullpen construction or bullpen usage. 

Hoyer isn't going anywhere. Nor is he about to dramatically shift his thinking on multi-year, high-dollar deals for relievers. But the hope is that Counsell will be more effective in how he deploys the tools in his toolbox and get more out of the group than Ross was capable of during his four years with the team. There's no one more adept at this than Counsell.

The Chicago Cubs will not win the 2024 World Series because Jed Hoyer refuses to compromise

As previously stated, if the Cubs win the World Series it will be due, in no small part, to Craig Counsell’s ability to manage a bullpen that Hoyer refuses to spend on. 

The bullpen is a microcosm of the problem with Hoyer and a growing number of baseball executives in general: they have a mantra of what will be successful and what won’t and they refuse to stray from that path. To be fair, before we dive into the negative, that mantra has led Jed Hoyer to being a World Series-winning General Manager and a President of Baseball Operations for one of the most storied franchises in all of sports. 

I’m not going to say the man doesn’t deserve the job he has or that he hasn’t had success. However, the thing that every employee and every organization must have in a landscape that changes as quickly as Major League Baseball is a willingness to be flexible, and in that area Hoyer appears to be woefully ill-equipped.

He wouldn’t bend on how he valued former Chicago Cubs legends Javier Baez, Kris Bryant, Anthony Rizzo or Kyle Schwarber. He wouldn’t spend big on free agents like Yoshinobu Yamamoto or Josh Hader. He wouldn’t trade prospect capital for Juan Soto, likely due to an unwillingness to spend dollars to keep him on the roster past 2024 which, alone, will cost the Yankees $30+ million.

As we make our way to 2024 the Cubs have added left-hander Shota Imanaga and infielder Michael Busch but in the process they’ve lost All-Star starter Marcus Stroman, infielder Jeimer Candelario, the best pitching prospect they’ve had since Mark Prior, and potentially Cody Bellinger.

The fact that the two additions to the Cubs 2024 roster were made less than a week before the Cubs Convention has to at least raise the question of whether or not this is yet another condescension by Hoyer to the fans. If that convention had not been on verge of happening, would those moves have been made at all? 

He claims to have more moves up his sleeves as we head toward spring training but if we're being honest, this team needs to make several more additions if they want to be serious contenders and time is running out for Hoyer to make them.

A signing of Cody Bellinger is a must.

A signing of Matt Chapman would allow the Cubs to slot Busch in at DH, Bellinger at 1st, Pete Crow-Armstrong in center and they could then trade Christopher Morel for a reliever on a cost-controlled contract like Emmanuel Clase.

That being said, Hoyer has not given any indication that any of those moves are reasonable let alone likely, and therefore he is the biggest thing standing in between this team and another World Series championship. 

The Chicago Cubs will win the 2024 World Series because the farm system is extremely balanced and absolutely loaded

The teams that have the ability to win championships are ones that are constantly improving. In order to be a team capable of improving during the season you need to have some combination of the following things:

1. Young talent that has not yet reached its ceiling
2. Players that begin the season in the minor leagues that can help the major league team at some point in the season
3. A farm system deep enough to trade talented prospects for talented MLB players that can help a team win now

The Cubs have all three of those things.

The Major League roster is expected to carry outfielders Pete Crow-Armstrong and Alexander Canario, infielder Michael Busch, left-handers Jordan Wicks Luke Little on Opening Day, all of whom have little experience on the largest stage. Beyond that, Morel still battled strikeout problems last season but he improved in every other statistical offensive category and if he can find a defensive position to even be average at he could take his play to an entirely different level.

There are also players that will begin the season in the minors that could help the major league club if there is an injury or a lack of performance. Players like Matt Mervis, Owen Caissie, Kevin Alcantara, Matt Shaw, Cade Horton and Ben Brown will all be opening the season in the upper levels of the minors and they’ll be just a phone call away from coming up and providing for the team in a pinch.

Beyond that, if the major league team is cruising but they appear to be just one or two pieces away from truly contending at the trade deadline, any of the players listed above will be extremely attractive to a trade partner due to their high ceiling and their proximity to the majors. If a team were more interested in players that are further away then they could look at up-and-comers such as Jefferson Rojas, Derniche Valdez, Alexis Hernandez or Moises Ballesteros.

Moral of the story, this team’s farm system is not only built to help itself in a time of need due to injury, it also has the ability to send several prospects away in return for a difference-maker at the trade deadline. 

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.