The Chicago Cubs have now gone 10 seasons since their historic World Series victory in the 2016 World Series. That seven-game triumph over the Cleveland Indians (now Guardians) represented a catharsis for both the franchise and their long-suffering fans.

The Cubs had gone 108 years between World Series titles and it took a remarkable rally from a 3 games to 1 deficit to defeat Cleveland. That victory changed the direction of the Cubs organization. Prior to the final out of that World Series, the Cubs were viewed as a lovable team that could never win the big one. The World Series victory meant that the team had tasted the sweetness of winning the championship and it was no longer about just having fun in the sun during day games at Wrigley Field.

As the Cubs prepare for the 2026 season, the team has aspirations of rising to the top of the National League and making a run at another World Series title. It will take a lot to get there because the Los Angeles Dodgers are the favorites to win their 3rd consecutive world championship and that team is formidable with Shohei Ohtani, Mookie Betts, Freddie Freeman and other stars.

Additionally, the Cubs have to compete with the Philadelphia Phillies, New York Mets and possibly others that want to be in the same position.

Cubs manager Craig Counsell appears to have an excellent team on his hands. The Cubs added 3rd baseman Alex Bregman through free agency and they already had Pete Crow-Armstrong, Michael Busch, Nico Hoerner and Seiya Suzuki in their every-day lineup along with starting pitchers Matthew Boyd, Edward Cabrera and Cade Horton.

Can Shota Imanaga get back to top form as a starting pitcher?

Chicago Cubs manager Craig Counsell (11) walks to the mound in the sixth inning against the Milwaukee Brewers during game five of the N025 MLB playoffs at American Family Field.
Mandatory Credit: Benny Sieu-Imagn Images

The Cubs appear to have the weapons to mount a challenge to the elite NL teams and win the National League Central since the Milwaukee Brewers appear to be diminished. However there are issues at hand for the Cubs.

The Cubs are very concerned about left-handed starter Shota Imanaga. He had a sensational 2024 season after coming over from Japan and taking his spot near the top of the Cubs pitching rotation. Imanaga had a remarkable 15-3 record with a 2.91 earned run average while starting 29 games, striking out 174 batters and pitching 173.1 innings. He made the National League All-Star team in his first year in the big leagues.

More was expected last year, but the Cubs did not have a pitcher who came close to that form. Overall, he was 9-8 with a 3.73 ERA. His strikeout total and innings pitched were down significantly. He struck out just 117 batters in 144.2 innings.

As disappointing as those numbers were, he was brutal in the second half of the season when he had a 5.17 ERA in his final 12 starts. He was also ineffective in the postseason. An early-season hamstring injury had an impact on his delivery, and the Cubs want to see improvement from Imanaga in spring training.

The Cubs presented Imanaga with a qualifying contract offer in 2026 that will pay him slightly more than $22 million this season. The 32-year-old left-hander is not under contract for the 2027 season, so he needs a return to form if he wants to get paid big money in the future.

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If he has an unimpressive spring and gets off to a poor start, the Imanaga era in Chicago could come to a sudden end.

Matt Shaw will have a new role with the Cubs

When the Cubs signed Bregman, it put Matt Shaw in a new role for the team. Instead of playing 3rd base, Shaw is now a utility player.  He can play 2nd base, 3rd base, shortstop and the outfield.

The 24-year-old Shaw was an up-and-coming player a year ago. He had been selected in the first round of the 2023 Major League draft out of the University of Maryland. It appeared that the team had big plans for him. He slashed .226/.295/.394 with 13 home runs and 44 runs batted in while playing in 126 games and having 393 at bats. Shaw struck out 94 times and he also received 38 walks.

The acquisition of Bregman means that Shaw is going to have to change his outlook and demonstrate that he can play multiple positions.

Shaw needs to show that he can handle his new role both physically and mentally. The latter may be much more difficult because he could get the message that he is no longer a primary player for the Cubs. That could turn out to be problematic.

However, Bregman suffered a quad injury last season with the Boston Red Sox and that cost him more than 40 games last year. Another injury to Bregman or other infielders is possible, and Shaw could end up playing a key role for the Cubs if he is mentally ready to do so.

The Cubs want to see Shaw is mature enough to handle his new role with the team and be ready to come off the bench with just a moment's notice if he is needed.