Cubs Predicted to Win World Series…in 2031

Let me open with apologies to those of you who despise anything that carries even a whiff of frivolity. When the alternative is covering one more rumor about which of the remaining free agents the Cubs are most strongly connected to, looking at who’s Will Leitch thinks will win the next 10 World Series titles is a breath of fresh air for me.

The bad news is that the Dodgers win in 2025, though the Orioles are going to beat them two years later to capture the crown they will lose to the Braves this year. It’ll take until 2031 for the “Just two before I die” crowd to rest in peace, as the Cubs prevail over the Red Sox 113 years after the two last met in the Fall Classic. The Cubs will make it back to the World Series the following season only to be defeated by the Yankees 100 years after Babe Ruth‘s mythical called shot.

Barring an eight-year deal with one of the remaining free agents, or maybe an extension with one of their young guys, no one on the current Cubs roster is under contract for the ’31 season. Dansby Swanson is committed through 2029, but only three others are even locked in through ’27. And of that group, Shōta Imanaga may be able to opt out a year or two prior. Justin Steele is a likely candidate for extension prior to his final arb year in ’27 and Christopher Morel is under club control through ’28.

Even though we rarely think too far beyond the current season, it’s eye-opening to peer more than five years into the future and see how much uncertainty exists. Unless you’re the Braves, in which case the whole roster is locked into club-friendly deals in perpetuity. Okay, they only have eight players under control through ’28 and three through the following year.

When it comes to the Cubs moving forward, I’m less concerned about whether and when they actually win another title. What’s more important to me is that they remain consistently competitive on an annual basis and don’t have to debase themselves with a multiyear rebuild at least once a decade.

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