150 Years of History: Breaking Down the Cubs’ All-Time 40-Man Roster

As a born-and-raised North Side Chicagoan, I've been a Cubs fan as far back as I can remember.

You know as well as I do, there were some pretty lean years for the Cubs, as in they didn't win a lot of games. They truly did earn the moniker "Lovable Losers."

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person holding blue Chicago Cubs cap
Photo by Blake Guidry on Unsplash

From 'Lovable Losers' to Championship Dreams

There were years when they were very close to getting over the hump, only to be undone in one painful way or another. In 2026, this team has its sights set on another playoff run and, who knows, maybe another World Series.

It would be a fantastic capstone to the franchise's 150th anniversary. Hard to believe they've been around that long, but the Cubs have been through it, and for many of us, we can't imagine what our lives would be like without this team in it. Some of the credit goes to Wrigley Field, but most of it goes to some of the legendary baseball players who wore the uniform.

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Wringley Field Home of Chicago Cubs
Photo by Heather Maguire on Unsplash

Building the Ultimate Squad: 40 Players and 3 Managers

So, the Cubs dug through 150 years of rosters and assembled the ultimate 40-man team, complete with not one but three managers and loaded with some of the greatest players ever to wear the uniform.

Some played on the Cubs' most recent World Series team. Some stood out when the team was awful, and others broke records and never made the Hall of Fame.

I didn’t have many disagreements with the selections, although I would’ve found room for Carlos Zambrano and Mark Prior.

You can see the complete 40-man roster right here. Take a look and decide for yourself: Did the Cubs get it right, or did somebody get robbed?

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