Chicago’s ‘Lovable Losers’ Secure Wrigley Home Not Built for Them; Spend Century Building Legacy, Chasing Illusive Series

By ADAM ECOM

Some teams are built in boardrooms. The Cubs were built in a city that could not stop arguing with itself. 

Chicago was never going to be a one-team town. The city was too big, too divided, too proud of its neighborhoods to let one franchise claim all of it. The North Side and the South Side had different rhythms, different loyalties, different ideas about what baseball was supposed to feel like. That divide did not create the Cubs — but it shaped everything about what they became.

The franchise that would become the Cubs did not arrive with that name. They came in as the White Stockings in the 1870s — Chicago's original National League representative. Over the decades to follow, as rosters turned over and the managers came and went, the names changed  along with them.—

Colts. Orphans. And finally, by the early 1900s, Cubs — a name that stuck not because anyone chose it deliberately. Instead, it fit!

No dramatic founding. No rival pushed aside. Just one (1)  franchise evolving until it found itself. The discovery accidentally came to fruition.

As the Cubs settled into and became nestled within the city's northern half, truth-be-known, Wrigley was actually constructed for not only a different team, but also one that competed in an entirely different League. Long story short, that league folded, thus paving the way for the team that would eventually become known as ‘The Lovable Losers.’ Obviously, The situation was less than ideal, though at least the team inherited their home, secured in that neighborhood, both of which came to define the Cubs more than any roster ever could.

Raised in Broad Daylight’s 

For most of their existence, the Cubs played every single home game in the sun. No lights. No night games. Just afternoon baseball on the North Side, season after season, decade after decade. It wasn't just a scheduling quirk. It became identity. The ivy. The hand-turned scoreboard. The bleachers full on a Tuesday afternoon. Wrigley during daylight is a specific thing — and the Cubs were shaped by it.

When the Lights Came On

Lights didn't come until 1988 — and even then, the neighborhood pushed back. These people weren't ready to give up their afternoons.

Though when the Cubs finally did flip the switch, nothing really changed — yet everything did. The night games came. The sellouts kept coming. The losses kept coming too. There were shots at glory that slipped away — 2003 still stings for anyone who was watching — and years where the roster gave fans just enough hope to hurt them again. But Chicago does not quit on its teams. The seats stayed full.

Then the Cubs started building — for real this time. New ownership. A front office that thought differently. A farm system that actually produced. The Wrigley renovations were not simply cosmetic; they were a statement. We're investing. We're serious. We're not going anywhere. The rooftop buildings across Waveland and Sheffield had already figured that out years earlier — fans who couldn't get inside just climbed higher and watched anyway. Wrigleyville had always found a way.

A Heavyweight City

This is Chicago. The city that gave the world Michael Jordan and Dennis Rodman. The Blackhawks, who play with a kind of controlled aggression that feels distinctly Midwestern — quiet until it is no longer. A city that doesn't just follow its teams, it holds them to a standard. Chicago fans are tough. They're loud. They know the difference between a rebuild and an excuse. They'll boo you, and they'll love you, and sometimes they'll do both in the same inning. They bleed their colors and they expect something back for it.

The World Series

The Cubs have been on the receiving end of that for over a century. By the time 2016 arrived, they were a built team, in a rebuilt park, in a city that had been waiting 108 years and knew exactly what it was watching. When the final out of Game 7 settled into Anthony Rizzo's glove in Cleveland, the longest curse in sports was finally broken, and a generation of lifelong heartbreak melted away into an all-night celebration at Clark and Addison. This truly was the miracle the Cubs faithful had been praying for with increasing frequency and intensity for over a full century. 

Then came the rebuild again. The core broke up. The roster turned over. And in 2023, they were back in the playoffs — young, hungry, and reminding the league that the North Side isn't done.

The rebuild is real. Whether this is the year or the year before the year, Chicago knows what a contender looks like — and they're watching closely.

Chicago - Wrigleyville Memorabilia

The Cubs have produced Hall of Famers, heartbreakers, and some of the most collectible cards in the hobby. THE BASEMALL regularly presents authenticated memorabilia and graded cards from across the full arc of North Side baseball — from the early legends to the 2016 champions.

Shop the Chicago Cubs Collection → https://thebasemall.com/collections/basemall-chicago-cubs

Up Next on BASEBLOG:

BASEBLOG | Chicago Cubs — The Moments

We're just getting started on the North Side. The collapses, the heartbreaks, 2003, and 2016. The full story of what it means to be a Cubs fan is coming. Stay with us.

Next up: Cincinnati. The Reds are one of the oldest franchises in the game — and the city that gave professional baseball its first professional team. That story is next.

— ADAM I. ECOM, Founder and Commissioner, THE BASEMALL

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