Chicago Cubs Could Attempt to Sign World Series Ace in MLB Free Agency

The Chicago Cubs could bring in another pitcher to star in rotation.

Brad Penner-Imagn Images

The Chicago Cubs head into the offseason looking to improve their weaknesses and bolster their strengths, just like every other team in Major League Baseball.

With some issues both in the lineup and the bullpen, Chicago's starting rotation was far from the top of the list in terms of the team's problems that led to a fourth consecutive missed playoff appearance. In fact, the Cubs ranked top-five in the league for starting rotation ERA and have an excellent core led by young stars Shota Imanaga and Justin Steele along with the dependable Jameson Taillon.

Chicago does not need to necessarily add a star or spend big money on another starter and could already be very solid once again with what's already in the clubhouse. However, the opportunity presents itself this offseason for the team to roll into 2025 not just with a very good rotation, but one that could have the potential to be the best in baseball. With a ton of high quality arms available and looking for some big money deals, Zachary Rotman of FanSided named Dodgers ace Jack Flaherty, who the team acquired at the deadline and have used him in huge moments throughout their World Series run, as a player that the Cubs should pursue this winter.

"A rotation consisting of Flaherty, Steele, and Imanaga holding the first three spots would be really tough to beat, and can help take this Cubs team to the next level," Rotman wrote. "Their rotation isn't their biggest weakness, but Flaherty is the kind of player the Cubs cannot overlook given the fact that he's great, familiar with the NL Central, and won't break the bank financially the same way that other starting pitchers will. Upsetting Cardinals fans would be a nice added bonus."

Flaherty spent the first six and a half seasons of his career with arch-rival St. Louis, but outside of a career season in 2019, he never really lived up to the billing. Flaherty continued to struggle in the back end of the 2023 season with Baltimore, but after signing a one-year deal with the Tigers ahead of the 2024 season, he turned back the clock and looked like a superstar both in Detroit and in Los Angeles this year.

While Chicago still needs to add to the bullpen and inject some more pop into the lineup, no Cubs fan would be mad if the team went out and signed one of the top starters on the market and established a dominant rotation either.