Losing is never fun. Unfortunately for Chicago sports fans, it has become the norm.

“It’s been a lot of losing seasons in a row. … As the season goes on, when losses start to pile up, you feel a bit of apathy towards the team,” said Luke Vandermillen, a longtime Chicago sports fan.

It’s been less than a full year since the major Chicago sports teams combined to win just 37.5% of their games. This shattered the previous worst combined win percentage from 1999 when the teams combined to win 40% of their games.

Despite the tough times, Vandermillen hasn’t questioned his support of the team.

“I’m a big believer in loyalty,” he said. “You gotta keep coming back, because eventually it’ll be a good season in there.”

The Chicago White Sox have had the poorest performance of all Chicago sports teams. Their 41-121 record last season represented the worst in the modern era of Major League Baseball, which began in 1901.

This season wasn’t much better as the South Siders stumbled to the finish line with another hundred loss campaign. Seth Fox, a Cubs fan and sports enthusiast, believes that White Sox owner Jerry Reinsdorf should be thankful that they still have fans.

“For them to have any fans at all — Jerry should be very happy because they put out a really bad product,” Fox said.

Fox said what stings the most about the state of Chicago sports and the year after year losing is the lack of financial investment in the teams by the owners. Despite having the third-largest market in the U.S., teams like the White Sox rank in the bottom three for total spending on players. 

“I think you have way too many people that are just working really hard in the city, not just paying for a ticket, but then to be told that these billionaires that get money from the city don’t have money to put into the organization,” Fox said.

Another one of the disappointing teams in Chicago has been the Chicago Sky.

“They have a lot of issues going on,” said Marie Kane, general manager for Radio DePaul Sports & Entertainment. “Based on what I’ve seen, morale is low on the team. It doesn’t seem like they are working together the way that a team should.”

After making big acquisitions in the last two drafts with players like Angel Reese, Kamala Cardoso and Hailey Van Lith, the team and its fans had high expectations.

Unfortunately, the spark of hope was snuffed out as the team posted a 10-34 record which is the second worst in team history. 

“It’s definitely disappointing … I do think to an extent, Chicago sports fans are used to it, for better or worse,” Kane said. 

Regardless of their frustrations, Chicago sports fans continue to support their teams.

“I just love how resilient Chicago fans are,” Vandermillen said. “No matter how bad the previous season was, there’s always excitement going into the next season.”

With the Cubs in the midst of a playoff run and the Bears boasting a 2-2 record through four weeks, there is some hope for success in Chicago sports.

The investment and intense connection fans have with their favorite teams isn’t always healthy though. For some fans that feeling of losing and disappointment in the team can carry into their everyday lives.

“A lot of what we do as sports fans is to live vicariously through our team,” said Vincent Peña, an assistant professor in sports communication and journalism at DePaul. “If you lose a lot, that just impacts you mentally, it can impact your physical health — especially for sports fans.”

Some fans like Mike Greco have found that it’s better to enjoy the ride as a fan rather than worrying about results. At age 54, he’s been a fan his whole life.

“I think in my 20s and 30s, I was definitely more invested and emotional about wins and losses and rivalry games and all of that,” Greco said. “But I think now I am just a fan.”

There’s more to sports fandom than just caring about wins and losses. The human experience is something that connects fans and makes watching their favorite teams more bearable since they can share it with others.

“There’s these deep connections that give you solace when your team is losing and also people to cheer with,” Peña said. 

The culture of sports is something that has only expanded over time. For Greco, those memories and shared experiences are too important to throw away over the current state of his favorite teams.

“Look, I was alive for the ‘85 Bears,” Greco said. “I can still sing the song. I can still tell you all the starters.”

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