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CHICAGO — Al Capone or Bugs Moran? Al’s or Mr. Beef? Alley honk or no alley honk?

Cubs or White Sox?

Chicago precedent dictates that one must choose a side, and most city-dwellers have.

Loyalties in the Windy City run deep, especially when it comes to sports. While Chicago’s basketball, football and hockey teams rally fans citywide, that unity often ends at baseball. The North Side’s Cubs and the South Side’s White Sox have duked it out throughout history, dating back to 1900 before the Sox even existed. The rivalry is one of the most famous in sports — but what’s behind it?

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How The Cubs, White Sox Rivalry Started

The Cubs began playing baseball in Chicago in 1870 as the Chicago White Stockings, joining the National League charter six years later. The White Sox originated in the Western League as the Sioux City Cornhuskers before Charles Comiskey, a former Chicago baseball player and manager, bought them in 1894. He moved the team to St. Paul, Minnesota, and renamed the group the St. Paul Saints.

But by 1900, murmurings began that Comiskey, a South Side native, was planning to start a new team in Chicago. Along with Western League President Ban Johnson, Comiskey and others aimed to rebrand the Western League as the American League and compete for prestige against the National League, of which the Cubs — then known as the Orphans — were part.

The Chicago White Stockings in 1870. The Stockings went on to become the Cubs — while the team that would one day become the White Sox took over the name White Stockings. Credit: Wikimedia Commons

A Secret Meeting

On New Year’s Day 1900, it was reported in newspapers that a “secret conference” was held in a parlor of the Great Northern Hotel. There, owners of the new league, which included Johnson and Comiskey, as well as James Manning and Matthew Killilea, agreed to work together to put teams in new territories, including Chicago.

“Comiskey will transfer the St. Paul team to Chicago, and after strengthening his aggregation by adding a number of clever players, will make his bid for public patronage at a park on the South Side,” according to a newspaper article.

The next day, Johnson denied the meeting took place as an “unfounded and untrue” story.

In response to the rumor of the new American League placing a team in Chicago, Cubs President Jim Hart said he welcomed a “war” between the leagues.

“If the break-up of the national agreement must come, let it come in a hurry,” he told reporters. “It cannot happen too soon so far as I am concerned. Under the present low condition of baseball, the war would help considerable to clear up the baseball atmosphere and let us know where we are standing. On the whole, it would be a good thing if the national agreement was broken.”

However, Hart’s invitation didn’t last long. A few days later, it was reported he had “hurled defiance at the men who want to place another club in his city.”

Hart “asserts that there will be no other club in Chicago without his consent, and that he will never agree to such a proposition,” according to The Minneapolis Journal.

Jim Hart, president of the Chicago White Stockings, the team that would eventually become the Cubs.
Charles Comiskey, owner of the Chicago White Stockings, which became the White Sox. Credit: Boston Public Library

Slugging It Out In The Press

The contention between Hart and and American League magnates continued to play out in the papers, particularly over a supposed “promise” Hart had made that Comiskey could place a team in Chicago.

“There must either be the most perfect understanding between President Hart of the Chicago baseball club and President Johnson and C.A. Comiskey of the American League, or else a deep hatred calling for constant vengeance is burning between them,” The Minneapolis Journal wrote in January 1900.

Both sides pressed on, determined to meet their goals.

By February, Hart announced that while he wasn’t afraid of a new team, the National League had enough players to create an auxiliary league as a “measure of protection” against an “invading” team in the city.

Conquering The Cubs-Sox Red Line Doubleheader

The feuding continued between Hart and Comiskey, with each taking opportunities to publicly insult the other.

“Mr. Hart has not kept faith with the American League,” Comiskey told The Minneapolis Journal in February 1900, asserting Hart had “tried to back out of” allowing a new Chicago team once Comiskey actually took him at his word.

Soon after, the American League officially announced its plans to place a team in Chicago, regardless of whether Hart wanted to stick by his supposed promise or not.

The American League “does not wish to engage in a baseball warfare, but will be ready to meet it if it comes,” Johnson said.

A photo of Chicago in 1900, the year the White Sox and Cubs rivalry started. Credit: Wikimedia Commons

Whole Hog Or None

Officials for the American League didn’t think the “presence of a club on the South Side would in any manner conflict with or injure the Chicago club,” Johnson said.

“We are on record that when it is proved we are injuring the Chicago club by putting in a club here we will drop the matter for all time.”

Chicago, which covered about 200 square miles and had a population of about 2 million, was big enough for two teams, Johnson said.

“We think it is entirely unfair and unjust that one man should have exclusive jurisdiction over such a great extent of territory,” Johnson said. “Hart asserts he is contending for a principle. It seems to us this principle is, ‘whole hog or none.’”

In response, Hart said it was a “free country” and the American League could open in Chicago — but not under the national agreement. Comiskey could place his team in Chicago “at his own peril.”

“While Ban Johnson and a few others are making some pretty strong talk about the differences existing between the two leagues in Chicago, it is not probable that there will be any clash between the big organizations,” according to a March 10, 1900, article from the Minneapolis Daily Times. “There is no reason why Comiskey should not be allowed to play in Chicago.”

Accepting Fate

In March, heads from the American League met in Chicago, hoping to hear how the National League was dealing with the news of an inevitable new team.

“The attitude of the National League regarding the invasion of Chicago by Comiskey’s team will be known then, it is thought, and action to ward off any fight will be taken,” the Minneapolis Daily Times wrote. “Whatever the objections of President Hart of the Chicago National League club are, Comiskey will go ahead as if nothing was in his way. Grounds have already been secured for Comiskey’s … aggregation, and a Chicago American League club is now considered a certainty.”

An agreement was eventually made to Hart that the National League would make its schedule first so games between the teams didn’t conflict — the Cubs and White Sox couldn’t play home games at the same time.

Center fielder Fielder Jones joined the White Stockings for their inaugural season in 1901. Credit: Wikimedia Commons

A Rivalry Is Born

Finally, Comisky announced his new team’s name: the familiar “Chicago White Stockings.”

“In the good old days when Adrian Constantine Anson was putting in his golden summers winning baseball pennants for Chicago, his team was known from one end of the circuit to the other as the ‘White Stockings,’” The Inter Ocean reported. “The old team turned out more stars, earned more money and gained a bigger reputation than any other club in the country. If Comiskey and the men who make up the new ‘White Stockings’ can duplicate this record, they will literally own the town before the end of September.”

Having secured his Chicago takeover, Comiskey swore to “give the patrons of the game in this city the best team that money can buy.”

The rivalry between the White Sox and Cubs was cemented.

“We will stand or fall on our merits as ball players,” Comiskey said. “If the players I have picked fail to make good we will buy other men, for I realize that the people who support the game in this town are tired of listening to excuses and hard-luck stories. What they want is a winning ball club, and I certainly will try to give them what they want.”

Play at first during the 1906 World Series. Credit: Boston Public Library/Wikimedia Commons

1906 World Series

The first Cubs-White Sox matchup occurred in the 1906 World Series. The Cubs were coming off an excellent season with an epic 116 wins, while the White Sox were known as the “hitless wonders.”

As it became clear the Chicago teams were going to face off, the city fell into a fury unseen in decades.

“The phenomenal interest aroused in Chicago and the middle west by the spectacle of two Chicago teams leading the National and American leagues, and by the prospect of seeing the two Chicago clubs battle for the world’s championship, has developed the fact there is considerable haziness in the mind of the general public regarding the world’s series,” the Tribune reported Sept. 30, 1906.

Gates closed at 12:30 p.m. two hours before Game 6 of the Cubs-Sox World Series started. A crowd outside with tickets couldn't get in. Credit: Boston Public Library/Wikimedia Commons
Police protect White Sox player Nick Altrock, a pitcher, from an adoring crowd during the 1906 World Series. He played with the Sox 1903-1909. Credit: Boston Public Library/Wikimedia Commons

A Fire Is Raging

The first day of the series was referred to as “Chicago Day,” commemorating “the most historic event that has occurred on Oct. 9 since the year 1871,” referring to the Great Chicago Fire.

“Today is the date set for the beginning of the greatest struggle in baseball’s history, the series for the world’s championship between two of the grandest ball clubs ever in knickerbockers, both belonging to Chicago,” the Tribune reported.

“Today a fire is raging through the city that has been smoldering for weeks past and will burst into its full fury at 2:30 o’clock … when Chicago’s two teams of champions face each other on the green battlefield. But it will be a harmless fire of loyalty to one team or the other, inspiring in its grandeur but not terrorizing or disastrous in its results”

News reports described a “pent-up enthusiasm … raging in the breasts of the many thousands of fanatics ever since it began to be possible for Chicago to win both major league pennants and bottle up all the baseball honors of the year within its own confines.”

Some headlines called the event a “civil war.”

Picking A Side

Leading up to the first game, both teams kept their starting pitchers a secret. Newspapers reported Chicagoans were betting on the outcome, but more so in friendly wagers than in big bets. Bets in New York were another story — East Coast spectators put down $500-$1,000 for both teams.

On the first day, the odds ranged from 7 to 5 to 2 to 1 in favor of the Cubs.

“Nearly every fan in town has a preference, and many of them want to express it in coin as well as noise,” according to the Tribune.

The Chicago White Sox versus the Chicago Cubs in the 1906 World Series. Credit: Boston Public Library/Wikimedia Commons

A Victor Is Named

The games alternated between both teams’ home fields. The Cubs won games 2 and 4 while the Sox clinched games 1 and 3.

The White Sox broke the tie in Game 5 after the South Siders tied the game in the third inning and cranked out 12 hits to win the game 8-6.

With growing anticipation and momentum in favor of the White Sox, Game 6 saw a recorded attendance of 19,249 — with “almost as many more” outside watching. Those outside received news of the game from within the park via a word-of-mouth chain.

A ball from the 1906 World Series. Credit: Wikimedia Commons

The White Sox walloped the Cubs with 14 hits and strong pitching from Doc White, winning 8-3 and taking the series 4-2.

“With the wide White Sox margin established early and the White Sox rooters already celebrating their triumph, the men who came to cheer the West Siders never gave up until the fining innings, hoping against hope that the Spuds would rally, cheering every opening which promised anything, and mentally hoping for one of those unexpected turns which make baseball the most uncertain and most popular of sports,” according to the Tribune.

The following day, the Tribune ran a cartoon titled, “Comiskey at Home” that depicted Comiskey in his living room sitting on a plush chair with his feet up, surrounded by small bear skin rugs and a World Series pennant on the wall.

Other Incidents

The rivalry took off even further in 1920 after it was exposed the White Sox had fixed the 1919 World Series, which “[scarred] a generation of Sox fans,” said Jack Silverstein, Chicago sports historian and author of “Why We Root: Mad Obsessions of a Chicago Sports Fan.”

In the 1940s, there came another twist: The NFL’s Cardinals team left the North Side to play games at Comiskey Park, again pitting the two geographic areas against each other with the Cubs and Bears playing at Wrigley and the White Sox and Cardinals playing at Comiskey.

Later, in the 1960s and '70s, “Cubs fans developed their own bragging rights,” Silverstein said. “Sort of a big brother-little brother element that Sox fans viewed as arrogance and Cubs fans viewed as a smirking ‘just the way things are.’”

As Cubs home games became more and more party-like in the '70s, and with the Cubs’ WGN deal making them a national team, “it was as if the Cubs were a ‘Chicago team’ as well as a national team, while the Sox were ‘just for Sox fans,’” Silverstein said.

This was around the first time the nickname “lovable losers” was used with the Cubs. It set the tone for how they would be viewed in the next generation, Silverstein said.

“When the Cubs lost, they were celebrities, and when the Sox won, they weren't the Cubs,” Silverstein said. “In the 2000s, it felt as if the Cubs got more praise for losing the 2003 NLCS than the Sox got for winning the World Series.”

The 2005 World Series win by the White Sox was huge for the team, which had been treated as “runner-ups in their own city,” the sports historian said.

The White Sox celebrate their 2005 World Series win. Credit: Adam Zamora/Wikimedia Commons
The Cubs celebrate after winning the 2016 World Series. Credit: Arturo Pardavila III/Wikimedia Commons

2016 World Series

Before 2016, Chicago had not seen a World Series win since the White Sox took the prize in 2005. As the Cubs inched closer to the trophy, eventually winning the series in seven games, some White Sox fans lent support to their rival team with a “Chicago over everything” attitude. Others actively rooted for the Cubs’ opponents, the Cleveland Indians, or ignored the fanfare altogether.

One South Side bar offered free shots to patrons for every time the St. Louis Cardinals hit a home run during the playoffs leading up to the World Series. Other White Sox fans expressed annoyance at the excitement behind the Cubs’ historic win after a 108-year losing streak.

In the frenzy, White Sox supporters were insulted by national media outlets who appeared to forget the team's 2005 win, Silverstein said.

“White Sox fans can’t help to roll their eyes at the current Cubs fervor in this city — which at times has been treating this World Series like a once-in-a-lifetime event even though the South Side team won a World Series 11 years ago,” according to a story from USA Today.

Still, some chose to support the North Side team despite a devotion to the White Sox. Former President Barack Obama, a White Sox fan, congratulated the Cubs on social media, adding that “even White Sox fans are rooting for you!” Rapper and Chicago native Common, also a White Sox fan, told late-night host Seth Meyers that “a White Sox fan has to root for the Cubs.”

In an op-ed piece for the Tribune, lifelong White Sox fan Steven Lubet said he found himself rooting for the Cubs because the event was “one of the greatest stories in the history of sports.”

“In the end, my writerly instincts have eclipsed the prospect of schadenfreude,” Lubet wrote. “So yes, I will say it: ‘Holy Cow! Go Cubs, Go.’”

Stadiums

The Cubs and White Sox offer two very different game experiences, both with a rich history and generations of loyal followers.

A beautiful summer sunset hangs over Wrigley Field as the Chicago Cubs host the Cincinnati Reds on Aug. 2, 2023. Credit: Colin Boyle/Ecoglobalsociety

Wrigley Field

After playing at West Side Park II on Chicago’s West Side for 23 years, in 1916 the Cubs moved to Weeghman Park, now known as Wrigley Field. Weeghman Park opened in 1914 as the home of Charles Weeghman’s Chicago Whales team, which played in the short-lived Federal League. The stadium was named Cubs Park 1920-'26 before being renamed Wrigley Field.

The ballpark is bound by Addison Street, Clark Street, Waveland Avenue and Sheffield Avenue and is affectionately nicknamed “The Friendly Confines,” a moniker given by Hall of Fame Cubs player Ernie Banks.

The marquee at Wrigley Field as the Chicago Cubs host the Cincinnati Reds on Aug. 2, 2023. Credit: Colin Boyle/Ecoglobalsociety

The iconic stadium is synonymous with the Cubs and is known for its ivy-covered outfield wall, red marquee over the Addison and Clark entrance, bleachers, manual scoreboard and, for many years, its rooftop seats on surrounding flats.

The park’s capacity is over 41,000 and famously lacks a traditional parking lot. Wrigley Field was the first Major League Baseball park to have live organ music in 1941 and was also the last MLB park to get lights for night games in 1988. It was deemed a National Historic Landmark in 2020 and is the oldest ballpark in the National League.

Wrigley Field’s significance on the North Side is substantial — the surrounding area, which sits between the Lakeview and Uptown communities, is known as Wrigleyville. Its high volume of bars and restaurants make it a lively and baseball-focused neighborhood that often sees large crowds before and after games. When the Cubs win, a blue flag with a white “W” is flown at Wrigley, and fans sing, “Go Cubs, Go.” When they lose, a white flag with a blue “L” is flown.

In recent years, the Ricketts family, which owns the team, has facilitated a number of major renovations at the park and around Wrigleyville, including the addition of a jumbotron, offices, a retail complex and a hotel. Still, Wrigley Field remains one of the most recognizable stadiums in baseball and locations in Chicago.

A dramatic sunset and clouds over Guaranteed Rate Field on Aug. 9, 2023. Credit: Colin Boyle/Ecoglobalsociety

Guaranteed Rate Field

The White Sox played at the beloved original Comiskey Park for 80 years before it was demolished in 1991 in favor of a newer version. The stadium is at the southwest corner of 35th Street and Wentworth Avenue in the Armour Square neighborhood near Bridgeport on the South Side.

The site of old Comiskey is now a parking lot for Guaranteed Rate Field, and the location of old Comiskey’s home plate is marked by a marble plaque on the sidewalk outside the stadium. The park was named Comiskey Park after its predecessor, then renamed U.S. Cellular Field in 2003. In 2016, it was renamed again to its current title: Guaranteed Rate Field. In 2005, the White Sox won the World Series on their home turf against the Houston Astros.

Fireworks light up the sky after a home run by Jose Abreu as the Chicago White Sox host the St. Louis Cardinals at Guaranteed Rate Field on May 25, 2021. Credit: Colin Boyle/Ecoglobalsociety

The ballpark pays homage to the original stadium with a similar “exploding” scoreboard, black and green color theme, cooldown shower and murals. It has gone through additions and renovations over the years to adjust seating and add more dining, drinking and entertainment options inside and outside the stadium.

Today, the park has a reputation for affordable tickets, with nearly unobstructed views throughout the park, as well as unique food offerings and fireworks show when the White Sox hit a home run and win.

In January 2024, the White Sox announced they were in “serious talks” to build a new stadium in the South Loop.

Fan Opinions

In design and feel, Wrigley Field and Guaranteed Rate Field showcase two completely different styles: retro vs. modern.

Guaranteed Rate Field has been called sterile by some fans who say it lacks the character and charm of the original Comiskey Park. Similarly, the upgrades at Wrigley Field have received mixed reception, with some approving of the modern additions and others complaining that the renovations changed the character of the neighborhood to be too corporate. Some have also criticized the older Wrigley Field for being cramped and having too many seats with obstructed views.

Fans contend the experiences at both parks are vastly different, with most preferring one over the other.

Longtime Chicago Cubs superfan Ronald “Ronnie Woo Woo” Wickers woos to cheering fans at Wrigley Field on Aug. 2, 2023. Credit: Colin Boyle/Ecoglobalsociety

“I live about a block away from Wrigley Field, so being a Cubs fan is the only option,” Lina Gebhardt told Block Club. “I look forward to Chicago summers in part because I can leave my windows wide open and hear fans cheering, music from concerts held at Wrigley Field — I can even hear the crowd sing ‘Go Cubs, Go’ from my apartment.”

Abby Arndt, a lifelong White Sox fan, said her first visit to Wrigley was so memorable she “might be a Cubs fan now.”

“The atmosphere, field, [and] location [are] so much fun,” she said. “I feel like Wrigley gives off much more of a ‘hometown’ feel than White Sox stadium.”

For some fans, like Kody Thames, it’s the bars and entertainment venues within walking distance that add to Wrigleyville’s charm — though he believes that uniqueness has dulled over the years.

“I used to love having Goose Island right outside the ballpark,” Thames said. “The old rooftops were great before the giant video board and new scoreboard went up. I loved the feel of the old Wrigleyville before the Ricketts corporatized it.”

Fans cheer as the Chicago White Sox beat the Seattle Mariners at Guaranteed Rate Field on April 12, 2022. Credit: Colin Boyle/Ecoglobalsociety

For others, the ease of securing a ticket, plus the low price, is a major draw of Guaranteed Rate Field.

“[I] can’t stand the Sox, but the tickets are cheap and plentiful, so I tend to go to more Sox games than Cubs,” said Alex Parker, a Kansas City Royals fan who also roots for the Cubs.

Social media user @snuggle_beast, a South Sider for the past 14 years, said she roots for the White Sox due to the more relaxed atmosphere at the park and how accessible it is to catch a game.

“[I] love that going to a Sox game is chill and affordable and not the insanity that is Wrigleyville,” she said. “I never step foot over there.”

In a 1988 Tribune article comparing the original Comiskey Park and Wrigley Field, the North Side venue was noted for being “comfortable and cute,” while the South Side park was “never particularly comfortable and never at all cute. It was a man's ballpark.”

“Wrigley Field smelled like popcorn. … Comiskey Park smelled like dead cigarettes and stale beer,” according to the paper. “Comiskey Park roared. Wrigley Field yayed.”

By The Numbers

176,579,169

Cubs attendance 1901-2023.

140,598,579

White Sox attendance 1901-2023.

Cultural Aspects

In Chicago, one’s preferred baseball team isn’t simply about baseball. It’s a way of life and a communal identity that fans possess — which has, in part, kept the rivalry alive for so long.

North Side vs. South Side; White Collar vs. Blue Collar

One of the most obvious splinters between the Cubs and White Sox is the difference in geographic location. The Cubs are on the North Side of the city and the Sox are on the South Side. In a city with a long history of racial divide, this has certainly been a factor in the rivalry.

“As in all matters in Chicago, there is a racial component between the North and South Side,” Silverstein said.

Even Ernie Banks, the first Black player for the Cubs, lived on the South Side due to racial segregation.

For people who live in Chicago, it’s not uncommon to largely stay on your side of the city, Silverstein said. That leaves many people without exposure to the other half.

“A lot of people on both sides of Madison rarely travel past the Loop,” Silverstein said, referring to Madison Street Downtown, which is about the middle of the city.

Fans pack the stands at Wrigley Field as the Chicago Cubs host the Cincinnati Reds on Aug. 2, 2023. Credit: Colin Boyle/Ecoglobalsociety
Fans pack the stadium during the Chicago White Sox’s home opener as they host the Seattle Mariners at Guaranteed Rate Field on April 12, 2022. Credit: Colin Boyle/Ecoglobalsociety

This physical divide has had major cultural and socioeconomic impacts throughout the city and helped define how the North and South sides — and their residents — are viewed.

For many years, the South Side was home to the Union Stockyards, steel mills and industrial factories near Comiskey, giving fans a blue-collar reputation.

“In Chicago, the common image of the Sox fan was the working-class, blue-collar guy,” author Dan Helpingstine wrote in his book, “The Cubs and the White Sox: A Baseball Rivalry, 1900 to the Present.” “That is probably an over-simplification of what divides the baseball city. Yet it had been the belief from the start, that Comiskey … drew the lunch-pail crowd.”

Today, with the stockyards long gone, many fans feel the blue-collar image is no longer accurate, though it is still undeniably part of the public perception.

In the late 1960s and '70s, the Cubs also had somewhat of a working-class fan base with the “bleacher bum” era, which saw construction workers stopping by games between shifts to heckle opposing outfielders, Helpingstine wrote.

By The Numbers

17

No-nos by the Cubs.

20

No-nos by the White Sox.

On the other hand, the Cubs fandom has been accused of being filled with “yuppies,” out-of-towners, “teeny-boppers,” “pseudo-experts” and bandwagon fans who aren’t as invested in the game as White Sox fans. The traditionally white North Side has been known for its high population of young professionals, and Wrigleyville has a reputation for attracting suburban visitors and catering to a frat boy-style atmosphere. The fans have also been accused of the “sneer factor” — looking down at their South Side counterparts.

“Cubs fans look down on Sox fans as blue collar,” a fan told the Tribune in 2005. “But Chicago is a blue-collar town. And it’s not like I’m Miss Blue Collar. I’m a lawyer.”

Part of the Cubs fan identity is also the allegiance with which supporters have stuck by a historically losing team, something only the most devoted fans practice — though not necessarily a trait some White Sox fans respect.

“True Cubs fans (not the generic kind crawling out of the woodwork these days) take everything in stride,” wrote reporter Douglas Hamm in 1984. “They have epitomized the definition of an honest to infield baseball fan for the last 39 years. They could write books about frustration, but each page would be dripping with joy.”

By The Numbers

3

Each team has won the World Series three times.

17 vs. 6

The Cubs have won the pennant 17 times, while the White Sox have done it six times.

21 vs. 11

The Cubs have been in the playoffs 21 times, while the White Sox have been in the playoffs 11 times.

Good Guys vs. Bad Guys

Within the North Side-South Side divide has also been at times the perception of good guys (the Cubs) versus the bad guys (the White Sox).

With their red, white and blue colors and cultural association with white and suburbanite fans, the Cubs have long had an all-American image. With nicknames like “The Boys in Blue” and logos that conjure up images of cute baby bears, the team has often been looked at as wholesome. Even monikers like the “lovable losers” evoke a sense of support and forgiveness in the public eye.

On the other hand, the working-class image of the White Sox has created an air of toughness and real gumption in the fan culture. This became legendary in the 1990s when the team was looking for a new uniform style, one that would resonate with old-timers as well as the South Side’s changing demographic, which had seen an increase in Black and Latino residents, according to WBEZ.

YouTube video

The team decided to go with pinstripes and an Old English-style Sox logo with a black and silver theme — “borrowed (or stole) from the black, white and silver look of the Los Angeles Raiders football team” which was a “color scheme that was very popular amongst gangster rappers on the West Coast,” according to WBEZ.

Famous rappers like Eazy-E and Dr. Dre were spotted wearing the new logo; Ice Cube sported the hat in N.W.A. music videos.

“When Dre started wearing that White Sox hat, everybody started wearing that White Sox hat,” Chicago radio personality Mario Smith told WBEZ. “Dre wearing that White Sox hat changed the world.”

Crosstown Games

The Cubs and White Sox have played each other off and on throughout history. Always highly anticipated and well-attended, the crosstown matchups are coveted events that draw huge attention citywide.

City Series

The teams first began playing each other as part of the post-season City Series games 1903-1942, turning into a best-of-seven series in 1905. The first game resulted in a tie, and the White Sox ultimately won 95 overall games (including the 1906 World Series) with the Cubs taking 62. That 39-year run saw notable moments such as 19-inning ties, cheating scandals on both sides — and lemons being hurled at players.

Boys Benefit Games

From 1949-'72, the teams played a single Boys Benefit game each year to benefit boys’ baseball organizations Chicago Cubs Baseball for Boys, Inc. and Chicago White Sox Boys’ Welfare Fund, Inc. With the new series, newspapers expected “Chicago’s cross-town rivalry will flare anew.”

One Boys Benefit game in 1964 was so well attended — with over 52,000 spectators — fans were allowed to stand in the outfield behind ropes and watch. The riveting game saw the White Sox debut new powder blue uniforms, and fans saw four White Sox home runs, plus one by Ernie Banks. The Cubs won that series 13-10.

Mayor’s Series

In 1981, Mayor Jane Byrne proposed that the Cubs and White Sox play two exhibition games following the players’ strike. The first game resulted in a 0-0 tie, and the Cubs won the second game. Another game was scheduled for 1982, but it was canceled because of snow storms, according to the Tribune.

The CTA gets into the spirit of the White Sox and Cubs rivalry by putting out dueling posters during Crosstown Series games.

Windy City Classic/Crosstown Classic

On April 30, 1985, the Cubs and White Sox played the first in a new series of showdowns billed as the Windy City Classic or Crosstown Classic. The exhibition series alternated between the teams’ home fields, with the first game at Comiskey Park.

These popular games were more about bragging rights and entertainment for the fans than competition. In interviews, players and coaches from both sides said they viewed the games more like a delicate practice than a full-throttle game. But after the first game, it was clear the series would be more intense than previously thought.

“Unless you saw it printed on the program or heard it uttered before the game, you’d have never guessed that Monday night’s war at Comiskey Park was merely an exhibition baseball game,” the Herald & Review wrote.

Ron Kittle, of the White Sox, said after the game that he’d “seen a lot of World Series games that weren’t this exciting,” while Sox manager Tony LaRussa said, “The winner tonight was the fan.”

The game set the tone for the fans’ modern-day rivalry, with 42,600 in attendance, some sporting “Cubs, chokin’ ugly” T-shirts. News reports noted that “the Cubs’ fans stood separate from the Sox fans,” who “were the ones laid back in their seats, feet kicked up, looking right at home.”

The series lasted through 1994, and the White Sox won the majority of games.

“The good of this game comes in the bragging rights,” the Northwest Herald wrote in 1991.

Tribune Twinbill Back To Back Series

In 1995, a Cubs-White Sox matchup saw two games played as the Tribune Twinbill Back To Back Series. One game was played at each park, and the Cubs lost both.

Interleague Play

Interleague play between the American League and National League began in 1997, allowing the Cubs and White Sox to play each other a handful of times each year. Once again, the face-off proved popular, with backing for an annual Cubs-White Sox series from sports writers and fans.

“The fans out there with ‘Let’s go Cubs’ or ‘Let’s go Sox’ ... it was pretty exciting,” Cubs first baseman Mark Grace said. “For the first time in a long time, I was excited and I was nervous. It was an intense atmosphere out there.”

The Crosstown Series trophy. Credit: Cubs/Twitter

Writer David Marran recalled a “late game shouting match” between the left field and right field bleachers at Comiskey Park, which was about one-third filled with Cubs fans.

“The fans saw a hard-nosed Cubs-Sox game, something they have not been accustomed to during the last nine decades of meaningless exhibitions,” Marran wrote. “The Sox’s Ray Durham demonstrated this was not a ‘Tribune Twinbill’ or a ‘City Series.’”

White Sox manager Ozzie Guillén remarked that “people come to the ballpark to boo and cheer for you. That’s part of the game.”

“I wish we could play the Cubs every day,” he added.

In 2010, a new sponsored prize called the Crosstown Cup trophy was introduced — a “symbol … of superiority for its civil war in baseball,” according to the Tribune.

“But it will be difficult — probably impossible — for any object to replace the joy of pure bragging rights.”

As of May 2024, the White Sox have a slight record lead against the Cubs in interleague play since 1997, but the Cubs have a seven-game lead over the White Sox in all-time matchups, according to South Side Sox.

1994 Michael Jordan Game

During Chicago Bulls star Michael Jordan’s brief stint in baseball, the basketball champion played a Windy City Classic game as an outfielder for the White Sox. Jordan had been playing with the minor league Birmingham Barons.

During the matchup at Wrigley Field on April 7, 1994, Jordan played right field. The public eagerly awaited a chance to see him play, unsure if he would be a major-league slugger or a basketball star out of his league.

Jordan received a standing ovation in the second inning, with news reports joking that “it had to be the first time in history North and South siders have agreed on anything.”

In the third inning, Jordan made an error that allowed the Cubs to score, and he was booed at his next time batting. In the seventh inning, he hit a ground ball along the third base line in a game-tying double.

“Michael Jordan … may never play a real baseball game in Chicago,” a sports writer for the Tribune wrote. “But he proved once again Thursday that he can steal the moment when he singled, doubled and knocked in two runs to lift the White Sox to a 4-4, 10-inning tie with the Cubs in front of 37,825 fans in Wrigley Field.”

Cubs shortstop Shawon Dunston said that although Jordan “may have been playing for the Sox … he is Chicago. Let’s not fool ourselves.”

Where To Watch On TV

The Cubs were long associated with TV network WGN, with some games airing nationally via WGN America. This, plus the Cubs’ ownership by the Tribune Company, was a large part of the team’s national exposure and advantage in popularity over the Sox.

In the early half of the 1900s, White Sox games were also occasionally broadcast on WGN, then bounced around to several local stations. In 1982, the White Sox began splitting game coverage between Chicago’s local Fox channel, WFLD, and the subscriber-based platform Sportsvision. However, fans accustomed to watching the games for free were reluctant to pay, especially when Cubs games were free and easy to access on television.

Later, WGN-TV and Fox Sports Network Chicago rotated coverage and commentary, with NBC Sports Chicago replacing FSN Chicago in 2005. At that time, each network would take turns to air both teams.

In 2020, the Cubs moved to its in-house paid service Marquee Sports Network, while the White Sox were broadcast on NBC Sports Chicago. As of 2024, the White Sox have similarly turned to a new broadcast streaming service called Stadium.

Ugly Events

While most of the contention between teams and fan bases has been verbal, there have been notable events that resulted in ejections, suspensions, the loss of an eye and plenty of embarrassment.

2006 On-Field Brawl

During the Crosstown Classic on May 20, 2006, at U.S. Celluar Field, a bench-clearing melee ensued after White Sox catcher A.J. Pierzynski and Cubs catcher Michael Barrett collided at home plate. Pierzynski was running home after Brian Anderson hit a fly ball into the outfield, but Barrett was crowding the plate, leading to a forceful impact.

A defiant and celebratory Pierzynski slapped home plate, but as he tried to walk away, Barrett grabbed him and punched his face. White Sox player Scott Podsednik, who was standing near home plate waiting to bat, jumped in to tackle Barrett away from Pierzynski.

Both dugouts emptied as players rushed the field to brawl.

Ultimately, Barrett, Pierzynski, Anderson and Cubs first baseman John Mabry were ejected from the game, with Barrett and Anderson receiving 10- and five-game suspensions, respectively. Pierzynski was fined.

Once the game resumed, White Sox second baseman Tadahito Iguchi hit a grand slam that helped the Sox win the game 7-0.

YouTube video

Fan Disputes

Fans have also been known to battle it out in the stands during crosstown matchups — with fights erupting between opposing fans as well as within fandoms.

In July 1999, a Cubs-White Sox game at Comiskey Park was stopped as “fans let fists do the talking” in the stands, according to the Tribune. The tension apparently hit its peak when it seemed the Cubs were going to win against the White Sox — revenge for the Sox sweeping the North Siders at Wrigley Field the previous month.

“Players and coaches always have insisted the crosstown rivalry meant more to the fans than to themselves, and it appears they were right,” reporter Todd Zolecki wrote.

In the same story, Cubs first baseman Mark Grace said he thought it was “awesome” that fans were so passionate.

“The fans are into it,” he said. “The Sox fans, the Cubs fans, it’s great stuff. I don’t care who you are, every player wants to play in front of a sellout crowd. … We play in front of a lot of sellouts, but not with this type of intensity. It’s a lot of fun.”

In recent years, some fan fights have been caught on video. Incidents in 2019, 2021 and 2023 show fighting and punches being thrown among spectators in the stands.

2008 Blinding Incident

The rivalry between fans turned violent off the field during a child’s birthday party July 19, 2008, when 34-year-old Robert Steele lost his right eye during Cubs-Sox banter gone wrong. Steele, a White Sox fan, was attending a family birthday party for a 2-year-old girl in suburban Huntley when a friendly discussion with two men, both Cubs fans, turned violent.

According to news reports, the ribbing turned argumentative when the Cubs fans teased that White Sox fans “had missing teeth” — a reference to the white collar vs. blue collar perception that shrouds both teams, with the narrative being that the South Side team has more working-class fans while the North Side team has more affluent fans.

During the incident, Steele fell to the ground and was kicked in his face by Boguslaw “Bob” Czapla and hit by Jerry Czapla. Both Czapalas, along with a third man named Maciej Trojnar, were charged in the attack, during which Steele lost his right eye, fractured his orbital bone and suffered a broken nose.

“Bob” Czapla was sentenced to three years in prison for aggravated battery and mob action, and Jerry Czapla was sentenced to six months in jail.

The fight was a rare example of the Cubs-White Sox rivalry exploding into serious injury.

Notable Crossovers

There have been many players, managers, executives and others who have been associated with both teams. Some of the most notable:

The Rivalry Today

The Cubs-White Sox rivalry remains today, but it “feels less intense” in recent years, Silverstein said. In 2020, Tim Anderson of the White Sox and Javy Baez of the Cubs were featured together on the cover of Sports Illustrated.

“Fans reacted more as shared victors than as rivals,” Silverstein said.

Still, the trash-talking, taunting T-shirts and decals — and occasional fan brawls — still occur. During matchups, White Sox fans have been known to turn Cubs winning traditions on their heads — like flying the Cubs’ losing “L” flag when the White Sox beat them.

Some narratives appear to have a stronghold on Chicago’s baseball culture — such as North Side vs. South Side and blue collar vs. white collar.

But as both teams have faced ups and downs, both fandoms have felt inspiration, desperation and apathy. Most fans feel secure in their selection, and both teams winning a World Series in recent memory “naturally defused the tension,” Silverstein said.

The Cubs leaving WGN for Marquee also had an effect on the rivalry because the Cubs were no longer nationally broadcast — they were on a private channel.

“It felt like the Cubs entered a bubble where no team exists but the Cubs and the team in the other dugout on a given day,” he said.

While the White Sox have their own problems, Silverstein thinks the rivalry may just simmer in the background until there is another opportunity for something big between the teams.

“Until we get another crosstown World Series, or at least flirt with one deep into September, I suspect that for the time being, the crosstown rivalry will remain on a low burner: dormant but waiting,” Silverstein said. “When it might erupt next is anyone's guess. Just make sure you're out of the path when it does.”

By The Numbers

$4.23 billion

Estimated value of the Cubs.

$2.05 billion

Estimated value of the White Sox.

Source: Forbes

Richie Gracia and his friends pose at the marquee during the Chicago Cubs' home opener as they host the Milwaukee Brewers at Wrigley Field on April 7, 2022. Credit: Colin Boyle/Ecoglobalsociety

What Fans Say

How do today’s fans feel about the rivalry? Is the glory about Chicago as a city above all, or would a true Cubs or Sox fan never root for the other side?

Like all things in this two-team town, there are differences of opinion.

“I grew up in … Rogers Park watching [the] Cubs and White Sox, but I’m primarily a Cubs fan,” said Imran Shahbaz. “I’d root for the Sox if they went to [the World Series]. I’d never root for another city. Chicagoan 'til Chicago ends.”

Laresa Lund, an Uptown resident who grew up a Cubs fan thanks to her grandmother but became a White Sox fan after moving to Washington Park, said she roots for the South Side but wants to see Chicago shine regardless.

The White Sox are “the people's team — scrappy, fun, mad drip, better hot dogs, better ice cream, more fun and varied fan base,” Lund said. “Cubs are for white suburbanites, but ultimately love my city so GO SOX GO CUBS GO CHI.”

Wrigleyville resident Gebhardt said she would also be willing to cross lines to support Chicago as a city, though she understands why some fans wouldn’t.

“I’d say the biggest difference between the two teams is the fans, and the fans are what makes the team so special,” she said. “While most Cubs fans probably wouldn’t root for the Sox in the World Series, I definitely would. Chicago can use all the wins it can get; [it’s] such a great sports city.”

Rob Holt, the “Cane Guy,” maneuvers his cane during Game Four of the 2021 American League Division Series on Oct. 12, 2021 where the Houston Astros beat the Chicago White Sox 10-1. Credit: Colin Boyle/Ecoglobalsociety

Lisa Olson said she lived in the Gold Coast in 2016 when the Cubs won the World Series, and she bought into the hype. She bought her first Cubs T-shirt — though she had a great time attending her first White Sox game the following year. She’s rooting for Chicago baseball in general, she said.

“We had a perfect day, and now we’re all hooked on the local teams,” Olson said.

But it’s not all peanuts and Cracker Jack for fans who hold steadfast in their allegiance to a particular team.

“I’ve always held firm that no Cubs fan would root for the Sox and vice versa,” said Carol Gugliemetti, a Cubs fan who grew up in Brighton Park on the South Side. “It’s a Chicago thing.”

Maria Torres-Martinez, a White Sox fan, said she rooted for the Cubs during the 2016 World Series, but those were special circumstances.

“I learned English watching Sox games with my Dad in the late 1960's early '70s,” she said. “South Side always.”

Although Torres-Martinez has taken her sons to some Cubs games, in her heart she’s a true White Sox fan.

“I've gone to Cubs games with our sons since they are all Cubs fans. They can't be perfect,” she joked. “I love going to Sox games; it's in my heart.”

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