It’s not betrayal — it’s Chicago rivalry at its finest.

Before the 2025 season, the last time either Chicago baseball team clinched a playoff berth was the 2021 White Sox — a team that overcame injuries to win the AL Central over a magical summer.

That was supposed to be the new norm on the South Side. White Sox fans had endured an ugly rebuild to establish a foundation of young talent and open a prolonged contending window.

As we came to find out, it was only a flash in the pan. The culture inside the clubhouse deteriorated as quickly as the soft tissue of their star players. Injuries, incompetence, and lack of leadership put the Sox in a downward spiral.

Meanwhile, the Cubs went through a mini-rebuild of their own. By 2021, Theo Epstein had stepped away, and the remaining pieces of the 2016 World Series squad were on borrowed time. The North Siders traded Kris Bryant, Anthony Rizzo, and Javier Báez. They released Jake Arrieta and later lost Willson Contreras to the rival Cardinals in free agency.

That much-needed reset paid off quickly. A new wave of Cubs prospects was joined by splashy free-agent additions, and the 2025 Cubs played like contenders from the jump — finishing 92–70 and returning to the postseason with a budding roster.

Because of their willingness to spend, the Cubs tore down a championship core and built another playoff team in just a few years. In that same window, their South Side counterparts have fallen so far that Sox fans are celebrating a 60–102 season as progress.

So as the Cubs now face an 0–2 deficit against the Milwaukee Brewers in the NLDS, a new debate has emerged: should White Sox fans be rooting for Milwaukee?

Some Cubs fans find it puzzling that lifelong Chicago sports diehards — the same people who scream “Bear Down!” and freeze in the Soldier Field seats every December — could possibly root against their own city for a team just 90 miles north.

Is it weird? Should it be frowned upon?

The simple answer: no. Not only are White Sox fans allowed to root against the Cubs, it should be expected. It’s part of the culture.

A Cubs fan who claims indifference toward the White Sox is one of two things — lying through their teeth, or a newcomer who hopped on the bandwagon during the 2015 playoff run. Those fans are too green to remember the sting of 2005, when the Sox hoisted the trophy and the Cubs were the punchline of baseball.

They sit on their high horse and say “Lions don’t concern themselves with the opinions of sheep.” And sure — that might be true for the newer breed of fan. If you weren’t around before 2015, you’ve always been the lion. You don’t know what it feels like to be the sheep — or worse, the black sheep.

But the rest of you? You remember. You remember the jealousy. The bitterness. The banter. You remember how Cubs fans mocked Tim Anderson’s flair, how they rolled their eyes when the Sox finally became must-watch TV.

It’s not hatred — it’s rivalry. And rivalry is what makes this city tick.

Chicagoans have always carried a chip on their shoulder. Sports fans here aren’t spoiled like they are in other major cities.

Since 2000, New York teams have made the playoffs 93 times. Los Angeles? 84 — with 12 championships.

Chicago? Just 43 total playoff appearances. And only five belong to the White Sox — the fewest of any major teams in America’s three biggest cities.

Winning here is rare. So when one team finally gets it, it’s natural for the other side to feel a little envy. Alfred Adler called it an “inferiority complex” — a persistent sense of inadequacy that drives the need to prove yourself. Every Chicago baseball fan, whether they’ll admit it or not, is guilty of that.

Look around sports — this isn’t unique to us. Lakers and Clippers fans fight in the stands. Mets and Yankees fans despise each other. You don’t think a Yankees fan would root for the Nationals against the Mets in a postseason series? Please.

The Cubs and White Sox have always rooted against each other. That’s not disloyalty — that’s local identity.

I vividly remember houses in my Chicagoland suburb flying Houston Astros flags during the 2005 World Series. And in 2016, plenty of Sox fans openly pulled for Cleveland — an AL Central rival — just to watch Cubs hearts break one more time.

Because division rivalries are about standings. City rivalries are about soul.

Yes, I’ve got friends who are Cubs fans. I’ve also got friends who are Packers fans. Doesn’t mean I ever want to see Green Bay win a single game. I’ve got buddies who root for the Eagles — I wasn’t exactly “happy for them” after the Double Doink.

That’s the beauty of sports. You can love your city, your neighbors, your friends — and still want their teams to lose every game they play.

It’s not weird. It’s honest. And there’s nothing more embarrassing than pretending you don’t care.

So yes, White Sox fans — root for Milwaukee. Root loudly. Root proudly. Root for discarded South Siders like Andrew Vaughn to send the Cubs home early. Because part of being from Chicago is picking a side… and actually having the backbone to mean it.