The city of Chicago has had its fair share of amazing championship seasons over the last 40 years. Everything from the Chicago Bears in 1985 and the Super Bowl Shuffle to the Chicago Cubs ending their 108 year World Series drought in 2016, to the Chicago Blackhawks dynasty run during the 2010’s, winning three Stanley Cups in six years.
Unfortunately, there have been a lot of bad seasons in between, especially of recent memory. The 2024 Chicago White Sox are on pace to be the worst team in baseball history, currently with a record of 21-58 and they are on pace to only win 40 out of 162 games but with the rest of their season to be determined, they are an honorable mention of worst seasons by a Chicago sports team for now.
With that in mind, this list will cover the 10 worst seasons of all time by Chicago sports teams. Apologies in advance to the fan bases of the Bears, Bulls, Blackhawks, White Sox and Cubs for triggering some bad memories.
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10. 1932 Chicago White Sox
To this day, this remains the worst team the Chicago White Sox have ever had. Granted, the sport of baseball was vastly different in 1932 with only 16 teams across the sport and the White Sox themselves played 151 out of 154 regular season games.
This team was horrendous to say the very least. Where do we begin to describe this atrocity? For starters, their longest losing streak was 10 in a row. home run total as a team was 36. Yes, that is correct: 36 total home runs as a team in 151 regular season games. Their leading home run hitter was Red Kress who was a utility player. He hit nine. No one on the team hit more than that. The White Sox pitching staff? Yikes.
Chicago White Sox pitching was a disaster
As a team, they ranked second to last in the American League in strikeouts only having a total of 379. The White Sox also ranked third to last in most earned runs allowed (723), hits allowed (1,551), and in walks (580). Two starting pitchers had identical records of 10-15: Sad Sam Jones and Ted Lyons. To add insult to injury, they had a 43 year old closer named Red Faber who had a miserable record of 2-11 out of the bullpen. This team was as bad as could be and certainly belongs on this list.
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9. 2018-19 Chicago Bulls
For a team that continuously ranks in the top five in attendance in the post Michael Jordan and Derrick Rose eras, Chicago Bulls fans have had very little to cheer about over the last 25 years. In the 2018 season, it was almost a certainty their opponent would walk away victorious. Chicago ranked 30th (dead last) in the NBA in three pointers made per game, with nine.
They couldn’t hit the side of a barn door let alone a perimeter shot. Granted they only took 26 three point attempts per game as a team, but that will not work in today’s era of perimeter play. Their largest loss in a single game came on December 8, 2018 in a home game against the Boston Celtics: 133-77. The team’s longest losing streak was 10 in a row from December 30 all the way until January 19 of 2019. Oh and the coaching staff? Horrible to say the least.
Coaching was fatal flaw for 2018-19 Chicago Bulls
The Bulls hired former Iowa State men’s basketball coach Fred Hoiberg in 2015. And while he did lead the Bulls to the playoffs in 2016, it was a disaster in 2017 with a record of 27-55 and it carried over into 2018. Hoiberg was fired after Chicago started the season 5-19.
Let’s say that again: the Chicago Bulls started the 2018 season with a putrid record of 5-19. Assistant Coach Jim Boylen took over and went 17-41 the rest of that season. There was so much turmoil surrounding this team from the front office to players on the roster. No stability whatsoever. Just a lot of dysfunction, too much to even get into. However, this was not the only bad Bulls team that we chose to put on the list. Find out later who else was picked.
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8. 2023-24 Chicago Blackhawks
Much like the Bulls, the glory days the Chicago Blackhawks experienced have been long gone for a number of years. Their last Stanley Cup victory was in 2015 and capped off an unbelievable dynasty run of winning three cups in six seasons. Since 2016, they have made the postseason twice in eight years. Last season however was as low as it gets.
While they have a young superstar in Connor Bedard, it was a struggle across the board. Bedard led the team in goals and assists with 22 and 39 respectively. The Blackhawks are one of the youngest teams in hockey and are in a rebuild right now led by head coach Luke Richardson and general manager Kyle Davidson, who are both in their third season with the franchise. So, as much as fans do not want to hear this, it is important to be patient and let this team develop.
7. 2012 Chicago Cubs
This Cubs team in 2012 was not very good to say the least as they were two losses shy of the all-time franchise record set back in 1962. Spoiler alert, don’t go too far because they are on the list, too. Anyway, 2012 was the start of a rebuild as they had a new front office in place led by President of Baseball Operations Theo Epstein and general manager Jed Hoyer. Chicago’s longest losing streak of the 2012 season was 12 in a row from May 15-May 27 when they had a record of 15-32 at the time. The worst loss of the season came against the New York Mets at home, 17-1.
On the whole, Chicago ranked near the bottom of the league in every offensive category: home runs, runs batted in, steals and so on. Not to mention the pitching staff was just as bad. Starting pitchers Jeff Samardzjia and Paul Maholm led the staff with nine victories each. That’s correct: no one in the pitching rotation was able to reach 10 wins for the season. All of this added up to an eventual record of 61-101 which was the second worst in all of baseball.
6. 1962 Chicago Cubs
This to date, the 1962 version remains the worst Cubs team of all time. They started the season 0-7 and had three different managers during the season. First it was El Tappe, who went 4-16 during the month of April and was fired. Lou Klein stepped in as interim manager and went 12-18 over 30 games before getting fired.
Finally, Charlie Metro took over the rest of the season going 43-69. The longest losing streak the Cubs endured was 10 in a row. Out of 10 National League teams, the Cubs ranked either second to last or last in the following categories with their pitching staff: hits allowed (1,509), earned runs allowed (725), most home runs allowed (159), and most walks allowed (601). It gets worse with their offense.
1962 Chicago Cubs offense was non-existent
Other than having first baseman Ernie Banks, third basemen Ron Santo, right fielder George Altman and left fielder Billy Williams, who produced the majority of the offense hitting 98 of the team’s 126 total home runs, no one else could be found. The 126 home runs ranked eighth out of 10 teams in the National League. The Cubs also ranked last in strikeouts on offense as they accumulated an astounding total of 1,044. This was a team to forget.
5. 2016 Chicago Bears
Sorry Bears fans, but this is just the start of going down memory lane. Or should we say, misery lane remembering some bad teams. This was the final season with Jay Cutler as the starting quarterback. Well, at least some of the season. Under head coach John Fox, Chicago had three different starting quarterbacks in 2016 and none of them were good.
The aforementioned Cutler went 1-4 in his five starts, throwing four touchdowns, five interceptions and 1,059 yards. Brian Hoyer started five games as well and had the same record. He ended up being the best of the three starting QBs, throwing six touchdowns and no interceptions to go along with 1,445 yards. Matt Barkley went 1-5 in his six starts during the year, throwing eight touchdowns, 14 interceptions and 1,611 yards.
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Losing hurt the 2016 Chicago Bears
Simply put, the Chicago Bears could not stop a nosebleed let alone their losing. They started the 2016 season 1-6 in their first seven games and the bad football would just continue from there. After reaching a record of 2-6 before the bye week, they went on to lose seven of their final eight games to finish 3-13, including giving up a season high 41 points in a loss to Washington in week 16. The Bears did not score 30 points in a single game during the 2016 season. However, this was not the worst Chicago Bears team we could find.
4. 2003-04 Chicago Blackhawks
The Blackhawks were not a good team two decades ago. Brian Sutter was the head coach during the season and it was one of many down years the team unfortunately went through before reaching winning glory in 2010. For the 2003 season specifically, they ranked 29th out of 30 teams in goals allowed.
Their leading goal scorer was Tuomo Ruutu with 23. Back when the National Hockey League had allowed ties during regular season play, Chicago ended up with 11 total. From November 9 until December 6, this team went on a winless streak of 14 consecutive games. Either a loss or a tie. That’s unheard of. In all, the Blackhawks finished with 20 wins total out of the 82 games played. Ouch.
3. 2022 Chicago Bears
As bad as the team was in 2016, 2022 was even worse. While through the first seven games, the Bears had a respectable record of 3-4, there was a major weakness for their offense: they were the only team who failed to break 3,000 passing yards. They had a mere 2,219. With all due respect, it’s hard to win games when your offense is stuck in the 1920’s instead of being caught up to the modern day game. The Bears defense?
They were far from being the Monsters of the Midway. More like the Bad News Bears as they gave up the most points and yards in the NFL. While they did end up with a top-three pick in the 2023 NFL Draft, this was a season to forget.
2. 2000-01 Chicago Bulls
This remains the worst team in Chicago Bulls history for an 82 game season. It is top two on the all time list of worst seasons by a Chicago sports team of all time. Tim Floyd was their head coach. They ranked last in points per game, averaging 88.
Only three players averaged double figures in points for the season: Elton Brand (20 points per game), Ron Mercer (19.7), and Metta World Peace, aka Ron Artest (11 points per game). At one point, the Bulls had a 16-game losing streak to have an abysmal record of 6-42 at that time, only scoring 100 or more points four times during that stretch.
1. 1969 Chicago Bears
When a team only wins one regular season game out of the 14 played, there is no debate of the worst single season teams in Chicago sports history. The 1969 Chicago Bears were many things: embarrassing, humiliating. Might even describe them as appalling. They were coached by Jim Dooley and their quarterback was rookie Bobby Douglass.
They ranked dead last out of 16 teams in points per game, only scoring 15, and had the fewest passing touchdowns in the league with 11. Running back Gayle Sayers was the lone bright spot on offense as he ran for over 1,000 yards and scored eight touchdowns. He was one of two Pro Bowlers on the team. Dick Butkus was the other. With all due respect, this was not the Monsters of the Midway. This was the Bad News Bears and it’s a fitting way to cap off the list of worst Chicago teams of all-time.