The Chicago Cubs victory in the 2016 World Series gets discussed as if it was yesterday but the fact remains that the Cubs are closer to 2026 than they are to 2016. Starting pitcher Kyle Hendricks is the lone player that remains on the Cubs' roster from the 2016 team and questions have arisen over the course of the next two seasons regarding when the Cubs' next contending window will open.
There is no question that the Cubs have taken steps toward returning to contention with the additions they've made this offseason but the team, as constructed, likely will miss the postseason for a third consecutive season. Hope may not be that far off for the Cubs as MLB's official website looked into the future and predicted the Cubs to make the World Series within the next ten years.
Will Leitch offered his analysis regarding a potential 2027 World Series matchup between the Cubs and New York Yankees:
"2027: Yankees over Cubs A century after putting together perhaps the greatest baseball team of all time in their Murderers' Row, the Yankees, after missing the playoffs the previous season and making fans claw their eyeballs out, stun the world by winning their 28th championship. Anthony Volpe is the World Series MVP, though it’s the homer by recent free-agent signee Vladimir Guerrero Jr. at Wrigley Field that seals the series over a plucky Cubs team."- Will Leitch, MLB dot com
Cubs fans may not be willing to hear this but 2027 does seem like a realistic target for when the team could make the World Series next. Until the Cubs show a willingness to sign a superstar free-agent player, the team is not going to be considered a legitimate contender to represent the National League in the World Series.
It would seem likely that the Cubs won't be willing to make that superstar addition until their top prospects are ready to be promoted to the Major League level. Top prospect Pete Crow-Armstrong could be at the Major League level by the end of the season with Brennen Davis on a similar trajectory. 2024 could see Kevin Alcantara and Alexander Canario reach the Major League level and that would leave 2025 as the year where the Cubs may truly be ready to contend.