The Chicago Cubs are entering the 2026 MLB season with one goal in mind: winning the World Series. With so many players not under contract for the 2027 season, the 2026 season is likely going to be the last go around for many on the roster.
Per Mark Feinsand, “With more than 40 percent of the roster potentially headed to the open market in the fall, the 2027 Cubs are almost certain to have a drastically different look than this year’s iteration. ”
And so, 2026 is one in which the Cubs are almost certainly gunning for a World Series, and certain MLB analysts think they have a great chance of winning it.
MLB analysts pick the Chicago Cubs third in their annual World Series winner draft
Every year, MLB.com analysts Will Leitch and Mike Petriello take turns picking teams in a “World Series draft.” In it, they take turns picking teams they think have the best chance to win the World Series. The Los Angles Dodgers were picked first, and the Seattle Mariners were picked second.
But then they picked the Cubs third:
“I am not blind to the fact that the Brewers are the three-time NL Central champions, and that the Cubs haven’t actually won their division in a full season since way back in 2017. And yet: I picked Chicago here, not Milwaukee. It wouldn’t be a season preview if someone wasn’t out here failing to fully respect Milwaukee, right? Why should this year be any different?
“Part of this is that winning the division isn’t a requirement for winning the World Series, so even if the Cubs finish second again, they could still get the ring, but also I’m encouraged by what I’ve seen of Shota Imanaga this spring, and I have hope they can unlock Edward Cabrera a bit. The lackluster rotation has had me down on this team the last few seasons – and I regret to say that I do not share everyone’s optimism about Cade Horton – but it’s at least deeper. The defense is great. They should hit.
“I have to admit, though: It’s very uncomfortable picking this team this high. You could probably order teams 3-13 here in any way you like. I sure hope Seiya Suzuki is healthy, though. We couldn’t have waited another day, Will?”
As one can see, the Cubs were picked high despite the analysts’ worry about the true quality of the pitching staff. That being said, they also did not pick the Brewers until 13th.
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