Chicago: The Capital of Wrong Side

When we first started discussing articles and blogs for our site, I was not quite sure what my first article should be. As the only native Chicagoan at Wrong Side Takes, I was embarrassed at the state of all my favorite teams and had nothing to hang my hat on for my introduction to the blog world. That’s when it dawned on me, I can hang my hat on being a LOSER. Chicago may have a few championships in recent decades, but those were before I was an adult so those obviously don't count. In my life, Chicago has been the city of losers.

The 5 major Chicago sports teams combined for the lowest winning percentage over a 1 season span in history. Chicago is the 3rd largest city in terms of population and in 2022 had the highest revenue from pro sports at $2.34 BILLION. In this article I will explain the painful history of Chicago Sports, and outlooks for each team moving forward as we continue the march of losing.

White Sox: Starting with arguably the most dramatic team on the list, the Chicago White Sox. The White Sox most recent title in 2005 was their first since 1959, a 46 year gap. Many did not expect them to go all the way that year and consider it a fluke. As a Cubs man myself, I tend to agree. In more recent history the White Sox won 93 games in 2021 and were 1st in the AL Central before falling to the Astros in 4 games in the ALDS. The Sox proceeded to go 81-81 in 2022 and 61-101 in 2023. The Sox are projected to win under 60 games this year. This 3 year skid is perfectly encapsulated by the Tim Anderson vs. Jose Ramirez bench clearing brawl in August of 2023 where fans across America saw TA get knocked on his ass, a familiar feeling to many White Sox fans. The highlight of the last 4 years: the Field of Dreams game, and the Campfire milkshake.

Outlook: The White Sox are owned by the worst owner in sports, Jerry Reinsdorf. Jerry has never, and will never, care about winning. If I were a Sox fan, I would hope attendance dips drastically forcing Jerry to make a move other than new concession snacks. Maybe a miracle prospect or 2 head to the South Side and the team can compete, but I do not see that happening.

Verdict: Though the Sox are looking better than they did in April and May, the 60 win number is still far away. The White Sox are WRONG SIDE.

Bulls: Continuing on the Jerry Resindorf train, we come to the Chicago Bulls. The Bulls are a worldwide brand name and a historic franchise full of championships, right? WRONG. The Bulls are 207-389 all time without Michael Jordan, a .532 winning percentage. Though the Bulls went to the stratosphere in the 90s with MJ, Scottie, and the rest of the dynasty, they were losers before and have continued to be losers after. The Bulls have benefited from 2 of the best draft picks of all time which were Michael Jordan and Derrick Rose. Derrick Rose went toe-to-toe with Lebron and the Heatles and had many great series against them, but only reached one Conference Finals. I’m not even going to get into the heartbreaking injury to Rose. Since D. Rose’s peak, the Bulls have been plagued by awful contracts, FA moves, and coaching decisions. None of these are more infamous than Jim Boylen, who former players have not been shy to criticize. They seemed to be on the right path when they brought in Billy Donovan, Lonzo Ball, Nikola Vucevic, and Demar Derozan. The Bulls went into the 2022 all star break leading a stacked Eastern Conference at 38-21. Lonzo has not picked up a basketball in 2 years, but did pick up his player option of $21.3 heading into the upcoming 2024-2025 season. Overall, the Chicago Bulls have had the luxury of drafting a few all time players leading to some recent productivity, but it has been nearly 25 years since their last title and I am tired of hearing about the Jordan years.

Outlook: Another Reisndorf team, I cannot say the outlook is positive. The team has been trying to trade Zach Lavine and Nikola Vucevic for quite some time but there is no market for their awful contracts. Demar Derozan recently departed for Sacramento in a sign and trade. The team traded Alex Caruso, one of the only bright spots on the team, to OKC for Josh Giddey. Giddey has some upside for sure, but how do you not get a single pick from the team that has ALL THE PICKS. This team has been in quite a bind since Lonzo’s injury, but simply has not done enough to stay in a spot to centend. As Reinsdorf likes to say, we contend for the Play-in tournament.

Verdict: The most Wrong Side team in NBA

Blackhawks: I will be nice-ish to the Blackhawks. Conor Bedard won ROTY but missed a significant amount of time with injury. Bedard looks to be everything he was expected to be as the former number 1 pick. However hockey is a team game and the Blackhawks missed the playoffs and had the 2nd lowest points in the league. The Blackhawks drafted a defenseman number 3 overall. The team is in the early stages of a rebuild, but I do not see them moving out of the basement anytime soon.

Outlook: The Madhouse on Madison is still one of the best places to watch a hockey game, but don’t bet on the home team while you are there. The Blackhawks are building something, but they will not be who takes the city out of the shadow of losing.

Verdict: Wrong Side again! (but we are building something)

Cubs: THE loveable losers return once more. The city was gifted with a group of extremely likable homegrown prospects that put an end the 108 year championship drought in 2016. One of the more magical runs in playoff history, culminating in a 3-1 World Series comeback against Cleveland, looks to be any Cubs fan’s dream. However, some around the city call that group “the dynasty that never was.” It’s hard to win a championship, I get that, but that group of players did not compete at the level they should have aside from that magical run. As always, a case of inconsistent bats and bullpen play were the story, as they continue to be today. Trading the main core of World Series champs in July of 2021 was a sad day. Many fans have been itching for a new star or two to head up to the North Side. The wish was granted over the last few seasons bringing in Cody Bellinger and Dansby Swanson. Heading into the 2024 season, the Cubs were ready to compete for the division, and began the season looking the part. Since May, the Cubs have had one of the weakest offenses in baseball as well as some of the worst bullpen play. I would like to apologize to Cubs fans reading this. The decline started as soon as I moved near Wrigleyville in May, so I take full responsibility for this decline. The Cubs are currently last in the division while having the highest payroll this year. Cody Bellinger does not seem to be a long term answer as the 3 year deal he signed this offseason has player options after each year. Dansby Swanson is hitting a slash line of .204 / .281 / .341, career lows in all categories. Shota Imanaga, who looked like the Cy Young early in the year, seems to be on the decline as well.

Outlook: Lets just hope we don’t have to wait another 108 years, but I am not counting my chickens yet. Maybe my grandchildren will have something to cheer for. The Cubs are not contenders as we stand today. YOU HAVE TO C IT. Do we have to?

Verdict: My Wrong Side energy is too strong.

Bears: I am sure many of you skipped to this section, so please go read the others. The long losing history of the Bears is well documented. Aaron Rodgers went 24-5 against the Bears in his time in Green Bay and Favre went 22-10. The Bears have 1 Super Bowl championship on the shoulders of one of the best teams ever and made the Super Bowl in 2006 before falling to Peyton Manning. The Bears have never had a QB throw over 4,000 yards in a season. Most elite QBs today throw for about 5,000 or more. I fell to my knees in the middle of my job at Culvers when the double doink happened. I have never felt any positive emotions when the Bears offense is on the field. However, the game has changed. In 2023 the Bears traded the number 1 overall pick to the Carolina Panthers who selected Bryce Young from Alabama. That trade and the resulting picks resulted in giving the Bears DJ Moore, Darnell Wright, Tyrique Stevenson, Tory Taylor, CALEB WILLIAMS, and we STILL have Carolina’s 2025 second round pick. For the first time in my life the Chicago Bears may be trending right side! As a Buckeye, the Justin Fields era has been hard to accept, but we are now in the Caleb Williams era. Caleb Williams continues to be a polarizing topic in the media, but I am here for it. He is well aware of the expectations this city and franchise has for him, and has done nothing but welcome those expectations. My favorite interview is when he said he wants to play in 1 city for 20 years and chase Tom Brady’s championships. He invented the new bear claw hand signal within hours of being drafted! The Bears knew they were getting a star and have loaded up in many spots to make Caleb’s transition to the NFL easier. Rome Odunze was chosen with the Bears own first round pick, shockingly having to give up nothing as Atlanta chose QB Michael Penix Jr. at number 8. The Bears defense was a top 5 scoring defense at the end of the season and hope to continue that play as they extended CB Jaylon Johnson and Pass Rusher Montez Sweat. While some in the media are criticizing Caleb before has has taken a snap, Nick Wright and myself are calling for a Super Bowl in the next 3 years.

Outlook: Football season is right around the corner and it can’t get here soon enough. The Bears are primed for a breakout year, so much so that they might fall flat on their faces. I am hoping the poise Caleb has shown so far translates to game day. I am also hoping the fans give the kid time to grow, a luxury they did not give Fields. The Bears odds to make the playoffs look like a high value bet, however I remember when Mitchell Trubisky was a highly bet MVP candidate in 2019.

Verdict: Saying the Bears have the most positive outlook on this list terrifies me, but here we are. Bears are Right Side (for now).

Written by: Joey Zolnierek