3 looming World Series champions the Cubs should sign this winter

The 2024 season could not have gone much worse for the Chicago Cubs. Sure, they managed to finish above .500, but despite adding Craig Counsell, Shota Imanaga, and Michael Busch to the mix, they finished with the exact same record as the 83-79 mark they ended the 2023 campaign with.

Despite all that went wrong for the Cubs this season, there's reason to believe that they'll improve in 2025. Virtually their entire core, especially if Cody Bellinger opts into his contract, will be back in 2025. Several high-end prospects like Matt Shaw, James Triantos, and Cade Horton are nearing their MLB debuts. Most of all, the Cubs have the ability to add to this roster via the trade market and/or through free agency.

Speaking of free agency, there are several key holes that the Cubs must address this offseason, and free agency is a great outlet to fill them. Several players from the New York Yankees and Los Angeles Dodgers — the teams participating in this year's World Series — will be hitting free agency in the offseason. Here are three in particular that this Cubs team should pursue.

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3) Tommy Kahnle, New York Yankees

The big Yankees free agent is Juan Soto, but chances are, the Cubs won't go near the lengths it'll take to bring him to the Windy City. While that stings a little, the Yankees do have other intriguing free agents, with Tommy Kahnle at the top of the list.

Kahnle is far from a big name, but he has been a dependable reliever for much of his 10-year career, as his 3.49 career ERA would indicate. He's 35 years old and would come with some durability concerns, but again, when he takes the ball, he's extremely solid late in games.

The right-hander was nothing short of lights out for the Yankees during the regular season, posting a 2.11 ERA in 50 appearances and 42.2 innings of work. His strong regular season has translated to the postseason, as he has not allowed a run in his seven innings of work. Walks are a bit of a concern, but Kahnle excels at avoiding hard contact and keeping the ball on the ground.

What makes Kahnle especially intriguing for the Cubs is that he can be trusted against both right-handed and left-handed hitters. He actually pitched much better against lefties than righties this season, holding them to a .169/.274/.301 slash line with only two home runs allowed. His change-up is an elite pitch, and helps him a lot against those left-handed hitters especially.

2) Blake Treinen, Los Angeles Dodgers

Similarly to Kahnle, Blake Treinen has dealt with some injury woes in recent years. He was limited to just five appearances in 2022 and didn't pitch at all in 2023, but was able to stay healthy for most of this season and was absolutely dominant.

Treinen posted a 1.93 ERA in 50 regular season appearances, striking out 56 batters compared to just 11 walks in 46.2 innings of work. That success has carried over to October, as the right-hander has allowed just one run in eight innings pitched. He has converted all three of his save opportunities after recording just one save all regular season long.

As you can see from this clip above, very few, if any pitchers, have the stuff Treinen has. When he's locating, Treinen is impossible to square up.

It really comes down to health for this 36-year-old. As his 2.78 ERA would indicate, Treinen has been a high-end reliever for most of his 10-year career. He simply has to take the ball. There's some inherent risk knowing his injury history, but the reward outweighs that risk with how good he is.

1) Jack Flaherty, Los Angeles Dodgers

The biggest strength of the 2024 Cubs was its starting rotation. Despite 24 ugly Kyle Hendricks starts, the Cubs rotation was tied for fifth in the majors with a 3.77 ERA. Justin Steele, Shota Imanaga, Jameson Taillon, and Javier Assad all have spots locked in, but the No. 5 spot is wide open. Sure, the Cubs can roll with a young arm like Ben Brown, Jordan Wicks, or even Cade Horton, but they can also try to field the best rotation in the majors by adding another high-end arm like Jack Flaherty.

Cubs fans might think of Flaherty as the injury-prone St. Louis Cardinals pitcher who hadn't quite lived up to his high potential, but in 2024, Flaherty has put together one of the best seasons of his career.

The right-hander posted a 3.17 ERA in 28 starts and 162 innings of work during the regular season, splitting time with the Detroit Tigers and Los Angeles Dodgers. His postseason results have been iffy, but he did deliver seven shutout innings in Game 1 of the NLCS and will start the World Series opener, showing what the Dodgers think of him.

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. 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.