Chicago Cubs' Rising Stars Expected To Emerge as 2029 World Series Contenders

An MLB expert has made a bold prediction about the Chicago Cubs and their future playoff fortunes.

Iowa Cubs player Matt Shaw stands at 3rd base during the first inning against Cleveland Cubs on Thursday, Aug. 15, 2024, at Principal Park. / Cody Scanlan/The Register / USA TODAY NETWORK

Chicago Cubs ownership made it clear that what happened during the 2024 season was viewed as a major disappointment.

Despite poaching manager Craig Counsell from the Milwaukee Brewers, the Cubs were still looking up at them in the NL Central standings. After winning 83 games for the second straight campaign, they finished in a tie with the St. Louis Cardinals, 10 games behind Counsell’s former club.

Looking to ensure that doesn’t happen again, the Cubs have been relatively busy this offseason.

They haven’t spent an exorbitant amount of money but made the biggest move of any team in the division acquiring star right fielder Kyle Tucker from the Houston Astros to be the new centerpiece of their lineup.

Depth was added at catcher with Carson Kelly agreeing to a two-year deal. Matthew Boyd was signed to a two-year deal to solidify the starting rotation and Eli Morgan was acquired in a trade with the Cleveland Guardians to bolster the bullpen.

The team could still use some reinforcements on the pitching staff, specifically the bullpen, as they are thin on experienced late-game options. Chicago is still in on the Roki Sasaki sweepstakes as well, which would give them a bonafide ace to join Justin Steele and Shota Imanaga atop the rotation.

There is a lot to like about this team for 2025, as they could easily be viewed as the NL Central favorites. Their competitors either didn’t make many moves to improve or took a step backward when it came to their roster.

However, what is so intriguing about the Cubs moving forward is the elite prospects they have knocking on the door of the Major Leagues.

Chicago currently has seven players ranked in the top 100 of MLB’s prospect pipeline. Six of them have already reached The Show or have an ETA of 2025 to make their debut.

Their top prospect, Matt Shaw, has a chance to break Spring Training with the Big League club after Isaac Parades was included in the Tucker blockbuster.

The Cubs are certainly hoping those youngsters pan out, or at the very least, become trade chips they can flip for established talent.

That upside has to be part of the reason why Will Leitch of MLB.com has picked Chicago to be the NL representatives in the 2029 World Series, where they will be facing off against the New York Yankees.

A clash between two of the most prestigious franchises in baseball would be a huge draw. 1923 was the last time they faced off for a championship, setting the stage for a rematch that would be nearly 100 years in the making.