Could Chicago Cubs Be Potential Landing Spot for World Series Champion?

It has been a very busy offseason for the Chicago Cubs with the team seeking to return to the postseason once again in 2025.

The Cubs have made a lot of moves this winter to improve a team that has won 83 games in the last two years. One of the more shocking moves of the offseason was Chicago pulling off a blockbuster trade to acquire Kyle Tucker from the Houston Astros.

Tucker is one of the best outfielders in baseball and he instantly makes the Cubs a better team. While the addition of Tucker was key for them, this is a team that also had some other needs heading into the offseason.

One of those needs was to improve a starting rotation that was solid in 2024, but perhaps lacked front-end of the rotation talent.

So far this winter, the Cubs have added two starters in Matthew Boyd and Collin Rea. While those are fine additions for depth, Chicago likely wouldn’t feel comfortable with either starting in a playoff game.

With not only making the postseason being a goal but winning games in October, adding a front-end pitcher to the staff still makes sense for the Cubs.

Tim Kelly of Bleacher Report recently highlighted the Chicago Cubs as a potential destination for Jack Flaherty in free agency.

“A starting rotation headlined by Shota Imanaga, Justin Steele, and Flaherty would give the Cubs a lot of buzz heading into a season they hope will send them to the playoffs for the first time since 2020.”

With two really good pitchers at the top of the rotation in Imanaga and Steele, Flaherty could settle in nicely as the third starter in the rotation.

While he hasn’t been the most consistent throughout his career, the 29-year-old is coming off an excellent campaign with the Detroit Tigers and the Los Angeles Dodgers. Before being traded to the Dodgers last year, the right-hander totaled a (7-5) record and a 2.95 ERA.

He continued to pitch well after the trade to the Dodgers and went on to help them win the World Series.

Adding a pitcher of that caliber to an already good rotation will help Chicago keep pace in what is going to be a challenging National League.

Since Tucker is potentially just a one-year rental, the Cubs should be having an aggressive mindset still this offseason to improve the team as much as possible.

If they are going to beat a team like Los Angeles or the Philadelphia Phillies in October, they are going to have to have multiple front-end starters in their rotation to keep up.

Even though the rotation is strong and is certainly capable of getting the job done in the regular season, adding Flaherty would help continue to make them a true contender.