Certain truisms in life stretch into the world of sports and beyond, one of which is that success breeds desire, and desire breeds sustainability. Following a 92-win season, the Cubs enter the 2026 campaign fresh off spending the second-highest amount of any team on free agency this past offseason. That means the expectations for this squad are higher than they’ve been in recent years. How do I know that? Because the boss man is feeling too.
In recent remarks to the media, chairman Tom Ricketts said the Cubs “obviously want to win the World Series every year.