Growing up rooting against a team and then wearing their jersey as a professional adds a fascinating twist to a player’s journey. It often brings up a mix of nostalgia, irony, and pride. Especially in a sports town like Chicago, where rivalries (like Cubs vs. White Sox or Bears vs. Packers) are deeply rooted. For prospect Pete Crow-Armstrong, he wasn’t exactly dreaming of donning Cubbie blue. His childhood fandom leaned toward Chicago’s rivals. Yes, a mix of loyalties that would make most North Side faithful raise an eyebrow.

Whether it was idolizing players outside the ivy-covered walls of Wrigley or following teams that routinely squared off against the Cubs, Crow-Armstrong’s early baseball world looked nothing like the one he now inhabits. But baseball, like life, has a way of writing unexpected storylines. Fast forward to today, and Crow-Armstrong finds himself at the heart of the Cubs’ future. A dynamic outfielder with Gold Glove-caliber defense, fearless energy, and a swagger that fits right in under the Wrigleyville spotlight.

The irony isn’t lost on him, nor is the opportunity.

“I’m convinced there was some part of him that was — I won’t say sadistic, but he wanted to screw with me as much as possible,” Pete’s father, Matt Armstrong, said to The Athletic. “He was trolling me at a very young age.”

In a city divided by baseball loyalties, Pete Crow-Armstrong has become a reason for all of Chicago to pay attention, even those who once rooted for someone else. But why such hate towards the Chicago clubs for Armstrong?

As a kid, Armstrong had one rule: don’t root for dad’s teams. His father cheered on the Chicago Cubs and Bears. But Pete, with a bit of rebellious flair, went in the opposite direction. For a stretch, he pledged his baseball allegiance to the Cubs’ archrival, the Cardinals, and in football, backed the Packers, the most hated foe in Bears country.

It’s the kind of childhood defiance that makes for a good laugh in hindsight. How? Because currently Crow-Armstrong patrols center field for the very team he once rooted against! With electrifying defense, swagger, and the raw tools that have scouts buzzing, he isn’t just another name on the roster — he’s part of the Cubs’ next-gen identity.

The Cubs are getting future-proof 

“It’s fun because I’m happy for the team and I’m happy for Pete,” the Cubs manager, Craig Counsell, said. Why not? In his first full season at the big league level, Armstrong is slashing .284 with six home runs. His stats include 21 RBIs, an .868 OPS, and 12 stolen bases through just 30 games. The defense was never in question — his glove has long been MLB-ready — but now the bat is catching up, and quickly.

So, what began as a playful rebellion has come full circle. And now, the kid who once rooted against the Cubs is giving them every reason to believe in the future.

However, what makes the story even more compelling is that Pete Crow-Armstrong wasn’t even the Cubs’ original target! Yes, you heard that right.

When the Cubs front office began trade talks with the Mets in 2021, the Cubs president, Jed Hoyer, had his eye on another prospect. Right-hander Matt Allan, a highly regarded arm who had recently undergone Tommy John surgery. Despite the injury, the Cubs were intrigued by Allan’s upside. The club believed they might be able to buy low on a future rotation piece.

But the Mets weren’t willing to part with Allan — at least not without steep conditions. As talks progressed, attention gradually shifted to Crow-Armstrong, a highly touted outfield prospect who had just undergone shoulder surgery himself. At the time, the trade was seen as a bit of a gamble on both sides. Well, what followed became history.

Baseball has a funny way of closing circles. And for Pete Crow-Armstrong, the journey from rooting for rivals to becoming a key piece of the Cubs’ future is as poetic as it is ironic. What do you think?