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The agony of Chicago sports, explained by a Chicago sports fan

Chicago sports haven’t always been ass. As someone born in 1987 who has never lived anywhere else, I can count 11 championships from the city’s teams in my lifetime. That includes six titles from Michael Jordan’s Bulls dynasty in the ‘90s, a run of three Stanley Cups in six years for the Blackhawks to start the 2010s, a beautiful White Sox World Series run in 2005, and the Cubs finally ending their 108-year World Series drought in 2016.

In that sense, Chicago sports fans have lived a privileged existence over the last three decades. It also doesn’t atone for the fact that, right now, Chicago sports are hot trash.

The football team is in the midst of a remarkable fall from grace that has the entire city calling for the quarterback and head coach to be axed. The basketball team, despite some preseason optimism, remains as garbage as ever. The Cubs would-be dynasty never got started and the Blackhawks’ dynasty is long dead. Meanwhile, the White Sox’s rebuild is entering a critical period that requires the type of financial investment ownership has never made.

Chicago sports are having a very bad, no good 2019, and it doesn’t seem like it’s going to get better any time soon.

The Bears are who they’ve always been


Chicago Bears v Philadelphia Eagles

Photo by Elsa/Getty Images

The Bears were the best kind of pleasant surprise last season. Coming off the failed John Fox era that accomplished the impossible and actually made Chicago apathetic about the city’s most beloved team, Matt Nagy’s first season in charge was a delight. They traded for a superstar in Khalil Mack, won 12 games (Fox won 14 combined in three seasons), ran lots of cool trick plays, turned their locker room into a nightclub after wins, and were both fun and good.

Then the double-doink happened. Now everything is terrible again.

The Bears have lost four straight games to put their season in a coffin. It’s hard to believe this team was ever 3-1 this season. There is so much blame to go around, so let’s just make handy list:

  • Nagy’s playcalling has been awful all year. Last season he seemed like the smartest guy in the room. This year he’s coaching scared and overthinking everything. The purported offensive genius has his team ranking No. 30 in yards per passing attempt and No. 27 in yards per rushing attempt. That is a nice way of saying the offense does nothing well.
  • All hope is lost for Mitchell Trubisky. He has lost not just the organization but the entire city. Trading up to draft this man over classmates Deshaun Watson and Patrick Mahomes will haunt the franchise for decades. It feels like it might be the franchise’s biggest mistake ever.
  • The offensive line is an F- and has been getting manhandled every week
  • The defense is still good but no longer great ever since Akiem Hicks (last season’s second best player) got hurt. The unit has fallen from No. 1 to No. 7 in defensive DVOA. Eddie Jackson was giving the entire city Mike Brown flashbacks last year and now he doesn’t have a pick this season. Roquan Smith has gone from a future star to a huge mystery. Even Mack has been quiet during the losing streak.

The offense being terrible and the quarterback being the reason is a story just too familiar for Bears fans. It’s not an exaggeration to say it’s been this way for 100 years.

At this point, it’s fair to wonder about the psychological impact of Trubisky on the rest of the team. Bears fans know bad quarterbacks all too well but this one feels particularly painful given the stakes. Also, the Bears don’t even have their first round pick this year (sent to the Raiders in the Mack trade), so everything is bad and there’s nothing to look forward to.

Optimism is dying for the Bulls


Atlanta Hawks v Chicago Bulls

Photo by Dylan Buell/Getty Images

I am one of the harshest critics of the Bulls front office, but they even won me over with their moves over the last calendar year. After rock bottom last season with just 22 wins, it seemed like the Bulls could make a major leap up the standings following the trade for Otto Porter Jr. and a few uncharacteristically smart free agents signings.

So much for that. Through seven games, the Bulls have the NBA’s easiest schedule and are just 2-5. They have lost to the Hornets, Cavs, Knicks, and a Pacers team without three of its best players. Meanwhile, the Bulls are almost fully healthy and still look like a disaster.

  • Jim Boylen sure feels like the worst coach in the NBA right now. He went 17-41 upon taking over for Fred Hoiberg last season and nearly caused a player mutiny in his the first week on the job. He was saying a lot of smart things to begin the season, but then ruined all his good will by installing a time clock and punch cards at the practice facility. OK boomer. More troubling is his lack of in-game adjustments this season: the rotation has been consistently awful and his pick-and-roll coverage schemes just don’t fit the personnel. He will tell you his spirit remains high despite all evidence pointing to the fact that he has no business being an NBA head coach.
  • Lauri Markkanen has been terrible to start the season. Shooting is the foundation of his game and he’s shooting 25 percent on threes so far. His defense has also been abysmal. He looks a lot more like a quality role player than a star.
  • Zach LaVine talked all summer about wanting to be an all-star this season in Chicago. He has started the year looking like the same player he’s always been, capable of flame-throwing scoring outbursts but still a poor decision-maker on offense and an awful defender. He is very obviously pressing right now, but there has been no growth. If LaVine is the star of your team, that team is going to have a concrete ceiling on how much it can accomplish.
  • Otto Porter Jr. has scored in double-figures exactly one time and just doesn’t look like himself.
  • Coby White won the Bulls a game vs. Memphis but has been pretty bad ever since. It would be foolish to count on a 19-year-old to carry the team this season.
  • Wendell Carter Jr. and Thad Young rule, but everyone else has been underwhelming.

You know things are going sideways when the team’s least bad loss was losing at home by 24 to the Raptors. This team still doesn’t have a star on its third year without Jimmy Butler. Boylen will also never lose his job because he kisses up to his bosses every chance he gets.

I still believe (maybe foolishly) the Bulls won’t be one of the very worst teams in the NBA this season despite losing to many of the worst teams in the NBA already. All that means is they will probably get the No. 7 pick again.

The White Sox need to get serious about contending


Kansas City Royals v Chicago White Sox

Photo by Ron Vesely/MLB Photos via Getty Images

The White Sox have not made the playoffs in the last 11 seasons. The last time they did make the playoffs, their roster featured Ken Griffey Jr. There have been multiple failed reboots since, with the common theme being the White Sox never make a splash in free agency. The biggest contract the team has ever handed out is $68 million.

It has to change this winter. The Sox actually made some meaningful progress last season, with young studs Yoan Moncada, Tim Anderson, and Eloy Jimenez all looking like cornerstones. Meanwhile, starter Lucas Giolito blossomed from afterthought to Cy Young contender. The Sox badly need to make a big signing or two going into next season. Will they?

Gerrit Cole would be ideal. Giolito remains the Sox’s only proven starter, behind him is prospects with varying degrees of upside. They also need an outfielder. Will Jerry Reinsdorf spend the money to make them a contender? Most of the fanbase will believe it when they see it, especially after last year’s lowball offer for Manny Machado.

I am hopeful about the future of this team. I just want to see them act like a serious big market club. They can spend $60 million this winter and still only have baseball’s No. 13 payroll. Make it happen.

The Cubs are fading fast


Chicago Cubs v Philadelphia Phillies

Photo by Hunter Martin/Getty Images

The Cubs made three straight NLCS appearances and won the World Series, but this purported golden era of the franchise has left the fanbase wanting more. Wasn’t this supposed to be a dynasty? Weren’t there supposed to be multiple waves of talent? Instead, the Cubs built a horrid bullpen last year, didn’t have enough contact hitters in the juiced ball era, and seem a little too comfortable to hang on to the World Series heroes.

The team mercifully fired Joe Maddon this winter a year too late. It did not inspire much confidence by hiring one of his former players on the 2016 team, David Ross, to be his replacement. The Cubs still have a ton of talent, but you won’t find much optimism anymore. They also made Wrigley Field feel corporate and soulless in its redesign.

As a lifelong hater and one of 18 living White Sox fans, this does not upset me.

RIP to the Blackhawks dynasty


San Jose Sharks v Chicago Blackhawks

Photo by Stacy Revere/Getty Images

The dynasty is dead even if so many familiar faces remain. Cap constraints robbed the team of so many promising young players because the team had little wiggle room to get out of the contracts they once gave to their Stanley Cup stars.

The defense has been a major problem for a few years now. The forwards can score but lack the depth they once had. The goaltending has been inconsistent at best. No one wants to root for Patrick Kane anymore.

The Hawks had the second fewest points in the Western Conference last season and have the third fewest at the start of this year. The tickets might be cheaper now, but this team has fallen a long way.


Chicago sports may be wholly uninspiring right now, but there are a few teams worth caring about.

Get on the Sky bandwagon


2019 WNBA Playoffs - Phoenix Mercury v Chicago Sky

Photo by Gary Dineen/NBAE via Getty Images

The Sky were the best story in the city this past year. Diamond DeShields is a worthy face of the franchise as one of the most athletic wing scorers in the WNBA. She is a star in the making. Courtney Vandersloot is dazzling with the ball, giving the team a veteran point guard who controls every aspect of the game and plays with a flair that recalls Steve Nash. The rest of the roster is young and emerging and should have the Sky in the WNBA playoff hunt for a long time.

But also: Sky fans just had to watch Elena Delle Donne win a championship with the Mystics, the MVP they once traded to Washington. So it’s not all good.

About the Red Stars …


2019 NWSL Championship

I’ll let my colleague Kim McCauley take this one:

“Chicago’s one good team lost a final, 4-0, and its best player immediately announced she was bouncing. That’s worse than just being bad.”

This is par for the course for Chicago sports at the moment. It would be funny if it wasn’t so sad.

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