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Chicago Sports Slump: A Tale Of Woes In The Windy City

A city of Stars And bright lights has fallen Into losing ways


1985 Bears Superbowl Trophy, Bulls NBA Title, 2005 White Sox World Series, Blackhawks Stanley Cup. Contributor: Associated Press / Alamy/ Charles Rex Arbogast
1985 Bears Superbowl Trophy, Bulls NBA Title, 2005 White Sox World Series, Blackhawks Stanley Cup. Contributor: Associated Press / Alamy/ Charles Rex Arbogast

Chicago is a city of Champions and some of the greatest players to ever play, from Michael Jordan, Scottie Pippen, Patrick Kane, Johnathon Toews, Kris Bryant, Anthony Rizzo, and the legendary 85' Defense. So, what in the world is going on in the City of Chicago?


Between slumps, repeated No. 1 overall picks, losing seasons, and missed playoff opportunities, the sports world in Chicago hasn't been in the state it is in in a long time. Since 2017, there has not been a playoff game won by the Bears, or a playoff series won by the Cubs, Sox, Blackhawks, or Bulls. This is new to Chicago since the last time no team had playoff success was in 2008, just two years removed from the Bear's last Super Bowl appearance. The city is fiending for a winner, and the constant disappointing year after another is beginning to cut deep into the passion of Chicago fans.


The Chicago Bears


Steve McMichael and William "The Fridge" Perry carry Head Coach Mike Ditka off the Field after winning the 1985 Superbowl. (AP Photo/Phil Sandlin, File)
Steve McMichael and William "The Fridge" Perry carry Head Coach Mike Ditka off the Field after winning the 1985 Superbowl. (AP Photo/Phil Sandlin, File)

Is this finally the team that Bears fans have been waiting for? Since the departure of Lovie Smith and company in 2012 the Bears have been searching for the face of the franchise and a guiding light to lead them back to the promised land. They have been a trainwreck of a franchise following that season going through coach after coach with the failed experiments of Marc Trestman, John Fox, Matt Nagy, and now Matt Eberflus.


The carousel doesn't stop at the head coaching position as the Bears have also been unable to find their man at quarterback. After Jay Cutler left Chicago the Bears decided to pass on future NFL Hall Of Famer, Patrick Mahomes in the draft and selected Mitchell Trubisky instead who was successful early in his career and may have turned out differently if it wasn't for a kickoff the post in the 2017 Wildcard game.


The future however is bright for the Bears, after bringing in General Manager Ryan Poles in 2022 they have trended in the right direction acquiring outside threats in Dj Moore and Keenan Allen, pass rusher specialist Montez Sweat, and many other key pieces that make up this Bears roster. All is up to the new star of the show, Caleb Williams from USC who is considered to be one of the best quarterback prospects to ever enter the NFL. If Williams is a star and the Bears keep trending upward we can hope to see them return to their 1985 glory.


The Chicago Cubs

Chicago Cubs Bring the World Series Trophy back to Chicago. (Steve Lundy/ Daily Herald Via AP)
Chicago Cubs Bring the World Series Trophy back to Chicago. (Steve Lundy/ Daily Herald Via AP)

The last championship in the city was brought to you by the 2016 Cubs. After 108 years of misery, most Cubs fans never thought the lovable losers could get over the hump and bring home glory. When the Cubs won people thought this was the beginning of a dynasty, with young rising stars all over the field from 2016 MVP Kris Bryant, to middle infield sensations Addison Russell and Javier Baez. In 2017 the Cubs lost in the National League Championship Series, looking like a team that would continue to build around its young core to compete for the World Series.


This is the opposite as the Cubs have not won a playoff series, only seeing October baseball twice since the NLCS loss to the Dodgers. The team has blown up, Kyle Schwarber was allowed to walk, Rizzo to the Yankees, Bryant is a Colorado Rockie, and Baez is in Detriot. The players many Cubs fans thought they'd be watching for 10-plus years now play for other clubs.


The Cubs are "the lovable losers". That is what they were for 108 years and probably will be for another 108 if they can't seem to put the right players in the positions to succeed. With as large of a market as Chicago is this team should compete year in and year out for division titles and National League pennants. The Cubs are not in the worst position of all the Chicago franchises but if they don't get things pointed in the right direction it could be a long time before we see a fall classic in the windy city.

The Chicago Blackhawks

2015 Chicago Blackhawks celebrating after there Stanley Cup win. (Via Jeff Haynes for Sports Illustrated)
2015 Chicago Blackhawks celebrating after their Stanley Cup win. (Via Jeff Haynes for Sports Illustrated)

The once-great dynasty in Chicago in the 2000s has turned into the laughingstock of the National Hockey League. The Hawks won 3 Stanley Cups in 6 years dominating the league and showing other teams what a well-run hockey organization looks like. They had some of the best players in the league, arguably the greatest American-born player ever in Patrick Kane, and Canadian stars Johnathon Toews and Duncan Keith. Year in and year out they were able to build winning team after winning team.


The fall was as drastic as the rise, since 2016 the Blackhawks have only had 1 winning season to show for finishing outside the playoffs six out of the last seven seasons. The once dominant franchise became quickly dormant becoming a shopping center for contending teams all over the league trading away a majority of the remaining core of their championship years.

Luckily for the Blackhawks, they were given a gift from hockey heaven in Connor Bedard, who looks to be the next great one not just for the Hawks but for the NHL as a whole. In only 68 games after suffering from a broken jaw, in which he returned to play sooner than expected, Bedard totaled 61 points an impressive performance for a rookie on a team where he had limited help. Of all the organizations in the city there is trust in the Blackhawks as they have proven in the past they won't waste a star player's potential on years of misery and losing.

The Chicago Bulls

From Left, Dennis Rodman, Michael Jordan, and Scottie Pippen hold up the 3 straight NBA titles for the Bulls. (AP Photo/Michael Conroy)
From Left, Dennis Rodman, Michael Jordan, and Scottie Pippen hold up the 3 straight NBA titles for the Bulls. (AP Photo/Michael Conroy)

Can anyone explain what is wrong with the Chicago Bulls? Did Michael Jordan curse them? Is it our punishment for the glory the city experienced in the 1990's? There's no real explanation as to why the Bulls have had to go through years of disappointment and injury-ridden lineups. The Bulls have had little to no success since the departure of Micheal Jordan and company going through a multitude of head coaches and players.


There was a thought that in 2008, when the Bulls drafted point guard and future MVP Derrick Rose they had finally begun to ascend back to the upper echelon of the NBA. They constructed a roster around him that had players such as Defensive Player of the Year Joakim Noah and all-star Luel Deng. Unfortunately for the Bulls, Rose came down on his Knee in a playoff game against the 76ers in which he tore his ACL in his left knee resulting in the beginning of the end of the Rose-Era in Chicago.


Since the exit of Rose and others, they have only been to the playoffs twice since their last series win in 2015 and have struggled to put together a roster that can compete for a championship. The Bulls will look to try and rebuild again after trading away Demar Derozan and Alex Caruso this offseason looking to enter a new era for the team. This is a struggling organization that has front-office issues that have been years in the making, If the Bulls can't right the ship fast there may be a new man at the helm soon enough.

The Chicago White Sox

Several players and staff of the White Sox Celebrate there World Series at the rally following their win. (AP Photo)
Several players and staff of the White Sox Celebrate there World Series at the rally following their win. (AP Photo)

When the White Sox won the World Series in 2005 there was a thought in the city that they could become the baseball champion this city deserved. The Cubs had not won in almost 100 years and the Sox were up and coming after sweeping the postseason going 16-0 not losing a single game. Unfortunately for Sox fans, they have not come close to the top of the mountain since 2005, only making the playoffs 3 times since 2005. A once-promising team has sunken into some of the worst years in sports.


The White Sox have struggled to build even a playoff-contending team in the last 15 years and have almost no playoff success at all, not winning a single series since their world title. They made the playoffs in 2021 and 2022 but, quickly blew up the roster trading away key players such as Dylan Cease, losing former MVP Jose Abreu to free agency, and dismantling a winning team trying to rebuild.


Things have only gotten worse for the Sox as in 2024 they have gotten off to a record start. Not the record you want to see as is one of the worst starts in MLB history, having them projected to lose over 120 games which would have been an MLB record. The White Sox are in trouble, the organization is in a place of difficult repair, the team requires total reconstruction, and now the city is slowly losing hope in a once-promising franchise.


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