3 offseason changes that need to happen if the Cubs miss the playoffs again

Chicago can leave no stone unturned this winter, especially if they fall short in their bid to return to the postseason once again.

Chicago Cubs Introduce Craig Counsell as Manager
Chicago Cubs Introduce Craig Counsell as Manager / Matt Dirksen/GettyImages
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Despite improved play of late, the Chicago Cubs entered Wednesday night's series finale against the Cleveland Guardians with just a 5.2 percent chance of making the postseason, according to Fangraphs.

At this point, it feels like the team's first-half struggles will prove too much to overcome and the team will be on the outside looking in when the expanded postseason field is set at the end of the year. This, on the heels of a historic September collapse last season, will be a bitter pill to swallow for a fanbase that's grown weary of the team's rebuild and small-market antics in recent years.

With Jed Hoyer's job on the line heading into a contract year and a mass of top prospects piling up at Triple-A, the 2025 season has all the makings of a now-or-never campaign. Here are 3 changes we need to see this offseason if this team is going to live up to expectations.

1. It's time for Craig Counsell to put his fingerprints on the coaching staff - and third base coach Willie Harris has to go

After signing the richest managerial contract in baseball history last fall, Craig Counsell more or less ran it back with the coaching staff he inherited from David Ross. This winter, with his feet solidly under him after one year on the job in Chicago, expect him to make changes to the staff around him and install some of 'his' guys.

Allowing Counsell to surround himself with people he feels compliments his strengths and weaknesses well could help him hit the ground running in 2025, hopefully helping the team avoid the prolonged struggles that plagued them this year. Where those changes come remains to be seen - but one area makes a ton of sense, at least according to the eye test.

It seems like we've seen bad sends from third base coach Willie Harris all season long - which is problematic, especially given the lengthy stretches where the Cubs were consistently running into unnecessary outs on the basepaths. As amiable and popular as Harris is, it feels like this is an area where Counsell can - and should - make a change.

2. The Cubs can't allow the luxury tax to handcuff them; it needs to be a non-factor as the front office works through the offseason

Despite being one of the most valuable franchises in all of sports, Chicago Cubs ownership continues to focus on maximizing profits and squeezing value out of every move - rarely digging deep and going toe-to-toe with teams like the Los Angeles Dodgers, Philadelphia Phillies or New York Yankees on key free agents.

That has to change.

A generational talent and likely future Hall of Famer headlines this winter's free agent class in Juan Soto and other top talents like Corbin Burnes would immediately make the Cubs a better team. Playing small market ball and treating the CBT as a soft salary cap can't continue to be the norm if this team is going to be a regular presence in October.

Tom Ricketts has the money. He's turned Wrigleyville into a cash-printing operation over the last decade-plus. Now, it's time to put those dollars into the pockets of the best players in the game and add the impactful star power this roster has lacked for years.

3. It's time to turn that vaunted prospect haul into big league talent, addressing glaring needs on the roster

In the latest MLB Pipeline update, the Cubs tied for the most top 100 prospects in the game with six. What separates Chicago from other teams, though, is all six of those players are now at Triple-A, giving them a half-dozen pieces that are just about big league-ready.

The problem is, at multiple positions, those prospects are blocked. So it's as simple as this: either trade from the 26-man or start packaging up these young players in order to shore up key areas on the roster. We know Hoyer has at least started to consider this based on his conversations with the Angels ahead of the trade deadline for catcher Logan O'Hoppe, but getting deals across the finish line will be a 'must' this winter.

The Cubs have a lot of quality pieces - but underperformance from key guys and the weaknesses on the roster have handcuffed the 2024 team and has them desperate for a season-ending hot streak to turn their fortunes around. If these prospects aren't going to have a road to the MLB roster, moving them may be the best move in his arsenal to get back to the postseason.

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