Chicago Cubs Named 'Practical Fit' for Former World Series Champion Pitcher

Should the Chicago Cubs pursue a trade for another starting pitcher?

Nick Ziegler | Feb 24, 2025

Sep 22, 2024; Milwaukee, Wisconsin, USA; Arizona Diamondbacks starting pitcher Jordan Montgomery (52) pitches in the first inning against the Milwaukee Brewers at American Family Field. / Benny Sieu-Imagn Images

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Chicago Cubs

With spring training games starting up for the Chicago Cubs, the team is getting prepared for the start of the new season.

It was a very busy winter for the Cubs this offseason. Chicago was able to make a lot of moves to improve the team on paper after a couple of solid seasons in a row.

After missing the postseason the last two years despite finishing over .500, the franchise made a couple of notable trades to shake things up.

Firstly, they acquired superstar outfielder Kyle Tucker from the Houston Astros. As one of the best all-around outfielders in baseball, Tucker gives the Cubs a superstar for at least one season.

In addition to acquiring the talented outfielder, they also bolstered their bullpen with the addition of veteran Ryan Pressly. The right-hander will be the closer to start the season, which was a weakness for the franchise last year.

Overall, the team has certainly improved compared to last year, but they still might be interested in getting better. Their pursuit of third baseman Alex Bregman indicated that they might be willing to spend on the right player and also that they are motivated to keep getting better.

One area that was a strength for Chicago in 2024 was their starting rotation and the unit is looking strong once again. However, they might look to add some additional talent if the price is right.

Zachary D. Rymer of Bleacher Report recently spoke about left-handed pitcher Jordan Montgomery being a practical fit for the Cubs.

The southpaw from the Arizona Diamondbacks is an appealing potential bounce-back player in 2025. After signing late with the Diamondbacks last winter, the veteran struggled mightily in Arizona.

Montgomery totaled a (8-7) record and a 6.23 ERA in what was the worst year of his career.

Even though 2024 was a disaster, there is reason to believe that he will be better in 2025 based on how he’s performed throughout his career.

In 2024 with the St. Louis Cardinals and Texas Rangers, he was able to put together a really strong campaign. Montgomery totaled a 3.20 ERA and helped the Rangers win the World Series.

For the Cubs, pursuing a potential trade for the southpaw would give them some additional depth in the rotation and also a pitcher who has the ability to start in postseason games, assuming he bounces back.

Due to his struggles, the Diamondbacks would eat a lot of the contract in any potential deal, making it a low-risk, high-reward potential move.

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