Expectations were on the rise for the Chicago Cubs heading into the 2024 season after they added manager Craig Counsell, taking him away from their National League Central rivals, the Milwaukee Brewers.

Chicago Cubs Could Soon Come To Regret Their Handling of Roster This Offseason

The improvement he was expected to bring never materialized, as the Cubs won 83 games for the second consecutive campaign.

With their playoff drought now at four years running and five out of the last six, pressure is mounting to find success on the field.

It could mean the difference between some people keeping their jobs beyond 2025 or not.

Transactions were made in the offseason to help move the needle in the right direction.

The biggest splash was right fielder Kyle Tucker being acquired from the Houston Astros. A legitimate 30/30 threat and one of the best position players in the league, he is the kind of offensive anchor the team has been seeking.

Veteran depth was added to the lineup with Jon Berti and Justin Turner to help push the team to the next level.

On the mound, Chicago signed Matthew Boyd in free agency to bolster the starting rotation along with Colin Rea. Ryan Pressly was acquired from the Astros in a separate deal with Houston, and Ryan Brasier was acquired from the Los Angeles Dodgers.

There is no doubt that upgrades were made by the Cubs.

But, the question remains; did the front office do enough this winter?

“Given that Tucker is a free agent this fall, the Cubs may come to regret not pushing the chips in and betting big this winter. If you only get one shot with Tucker, it had better work,” wrote Stephen J. Nesbitt of The Athletic (subscription required) in the preseason MLB power rankings.

Chicago was ranked by Nesbitt, Andy McCullough and Grant Brisbee as the No. 12 team heading into the regular season.

Their playoff odds currently sit at 56.5%, which is the highest amongst the NL Central squads.

The Brewers are No. 15 with a 23.7% chance to make the playoffs, with the Pittsburgh Pirates, Cincinnati Reds and St. Louis Cardinals ranked Nos. 22, 23 and 24. They have 14.6%, 14.6% and 25.4% odds of making the postseason.

While the Cubs are the odds-on favorites to win the division based on those numbers, there isn’t much room for error.

As Nesbitt shared, Chicago is an 84-win projected team heading into the year according to FanGraphs.

No other NL Central team is projected to finish with a record above the .500 mark, so 84 victories may get the job done.

But, it is fair to wonder if an opportunity was missed to really separate themselves not only in the division but become legitimate World Series contenders.