Chicago Bears

Chicago Bears: Chicago's Biggest Loser

Published Jun. 30, 2017 6:28 p.m. ET

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Jan 29, 2015; Phoenix, AZ, USA; General view of Super Bowl XX championship ring to commemorate the Chicago Bears 46-10 victory over the New England Patriots on January 26, 1986 on display at the NFL Experience at the Phoenix Convention Center. Mandatory Credit: Kirby Lee-USA TODAY Sport

After the Cubs thrilling World Series win, ending their 108-year drought, the Chicago Bears are now the city’s biggest losers, with 31 years since their last championship.

Happy Chicago Cubs hangover! If you’re just coming down off the high of the Cubs World Series win, welcome back to the Chicago Bears blog. As they sweep up the confetti from the Cubs World Series parade, there’s a new lovable loser in town and it’s the Chicago Bears. With the Cubs win, I’ve hit for the cycle, seeing every team in town win a title in my lifetime. For a lot of you, you either weren’t alive or don’t remember back to the 1985 season and your only memory of “Bears Super Bowl” is XLI in Miami when the best highlight of the game came on Devin Hester’s return of the opening kickoff.

With the Cubs win, I’ve hit for the Chicago sports championship cycle, seeing every team in town win a title in my lifetime. For a lot of you, you either weren’t alive or don’t remember back to the 1985 season and your only memory of “Bears Super Bowl” is XLI in Miami when the best highlight of the game came on Devin Hester’s return of the opening kickoff. If might seem like it was just yesterday since it’s so over-hyped in this town, but the Bears haven’t won it all for more than three decades!

If you asked 12-year old me which team in Chicago had the brightest future on January 26, 1986, I would have emphatically stated the Chicago Bears. They had the best defense in the league by a mile, a legendary running back in an era when that really mattered, a play-making quarterback and Da Coach Mike Ditka at the helm. Who knew that over 31-years later, we’d still be waiting for another Chicago Bears championship while all of the other major sports teams in Chicago have won titles.

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Who knew that over 31-years later, we’d still be waiting for another Chicago Bears championship while all of the other major sports teams in Chicago have won titles?

Many will tell you that Mike Ditka may have been the reason the Bears won a title but many more will tell you that Ditka is the reason they only won ONE title. Ditka let his own ego and the egos on the team get out of control and the Bears were never the same. They continued to make the playoffs years after their Super Bowl XX win, but weren’t able to close the deal.

The Bears teased us with a “ridiculous” season in 2006 and made it back to the Super Bowl, but a rain-soaked night and Peyton Manning put a damper on another championship. Jay Cutler was brought to town to solve the quarterback position, but he’s guided the Bears to one playoff win and an appearance in the NFC Championship game since 2009.

Whether anyone at Halas Hall wants to admit it, the Bears are in the midst of the second rebuild since Lovie Smith left town. The defense appears to be on the rise while we’re still unsure what to make of this offense. Can they rely on Jordan Howard and the ground game to burn the clock and keep them close enough so they can steal a few wins?

The Bears still need difference makers on both sides of the ball. That will come through the draft because over-spending in free agency hasn’t proven to be the winning formula over the last couple of decades. For the Bears to move out of the “biggest loser” spot in Chicago, it’s going to depend on Ryan Pace or whoever the next GM may be to start making better draft picks. First and second rounders need to step in and become immediate contributors and difference makers. They need to have opposing coaches game-planning around them.

Let’s look at each team in town and when they brought their most recent title to Chicago.

Oct 29, 2016; Chicago, IL, USA; A general view of the United Center during the second half between the Chicago Bulls and the Indiana Pacers. The Bulls won 118-101. Mandatory Credit: Jeffrey Becker-USA TODAY Sports

If you grew up in the 1990’s, these were the glory days for the Chicago Bulls. The Michael Jordan-led dynasty dominated the decade and spoiled a generation of fans. We took for granted that winning basketball was a way of life.

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The Bulls were the classic team that we watched grow up and develop into a championship caliber team. At first, there was Michael Jordan and then they started to add pieces around him. Scottie Pippen and Horace Grant were added and the team finally got past the Detroit Pistons to break through in the 1991 Eastern conference finals. They went on to beat the Los Angeles Lakers for their first title. They went on to beat win two more for their first three-peat from 1991 – 1993.

Whether you believe that Michael Jordan was sent to the penalty box under a super-secret suspension or just needed to get away and pursue his baseball dreams, the Bulls missed the NBA Finals in the two seasons he was away, but they bounced back nicely.

They added Dennis Rodman, Toni Kukoc and a new cast of supporting characters and rounded out another three-peat behind Jordan and Pippen from 1996 – 1998. As the only other Chicago team not to win a championship in this century, the Bulls haven’t won a title since Michael Jordan hit that shot – and no, he didn’t push off – back in 1998.

The Bulls bottomed out in the post-Jordan era and the early 2000’s were pretty awful. It looked like they might rebound with a new cast around top draft pick and local kid Derrick Rose. Injuries derailed a promising career and although they got back to the Eastern Conference finals, they couldn’t get past Lebron James the way so many teams could never get past Jordan.

Apr 8, 2016; Chicago, IL, USA; A general shot of a monument to the Chicago White Sox 2005 World Series championship in the snow prior to a game against the Cleveland Indians at U.S. Cellular Field. Mandatory Credit: Dennis Wierzbicki-USA TODAY Sports

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The White Sox ended their own drought in 2005 when they brought the first World Series to Chicago for the first time since the 1959 Series, which they had lost. The Sox are often looked at as the little brother in Chicago baseball, but for this season, they ruled the city and ended their own 88-year World Series drought.

I’ll admit, I’m not a Sox fan so I didn’t follow this team as closely as the other teams on this list. The Sox got off to a good start during the season but hit some rough patches through the season before getting hot late in the season and riding their terrific starting pitching through to their first World Series since 1917.

While I followed the 2005 playoffs, I didn’t outwardly root for the White Sox, but I was happy to see them win. It was good for Chicago and it may have been the catalyst for the Cubs and even other teams in the city to step up their game.

Oct 7, 2015; Chicago, IL, USA; Members of the Chicago Blackhawks raise the 2015 Stanley Cup championship banner during a ceremony before the game against the New York Rangers at United Center. Mandatory Credit: Jerry Lai-USA TODAY Sports

The Chicago Blackhawks had a long-suffering fandom of their own. And when I say suffering, I mean they survived the Bill Wirtz ownership era when he did everything he could to try to push fans away including not televising home games. After old man Bill passed away, the Blackhawks broke through in 2010 and brought their first Stanley Cup to Chicago since 1961.

The Blackhawks made a Stanly Cup Final appearance in 1992 when they were swept four straight against the Pittsburgh Penguins. They were just good enough to make the playoffs into the late 1990’s before the bottom fell out.

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Bill Wirtz passed away in 2007 and that’s when things started to turn around. (Really, some of their Cup pieces had already been in place). Bill’s son Rocky took over and they started to re-build the organ-i-zation from the top down. They added former Cubs exec Jim McDonough who started to turn the team around on and off the ice.

Perhaps one of the biggest moves the team made was firing beloved ‘Hawks player and coach Denis Savard and replacing him with Joel Quenneville ahead of the 2008 season. At the time, it was an unpopular move among Blackhawks fans but Coach Q was the right guy to position the franchise to make a run at a Stanley Cup. The ‘Hawks lost in the conference finals in the ’08-’09 season but were poised for bigger things the next season.

Powered by a core of young talent and key veteran free agents, the Blackhawks brought the Staney Cups back to Chicago after the 2009-2010 season. But just one Cup wouldn’t be enough for this group. They created a hockey dynasty by bringing back Cups in the 2013 and 2015 seasons. The strict salary cap has made it tough for the ‘Hawks to sustain their Stanley Cup ways, but with their core guys still in their prime, they’re still well within their champioship window.

Nov 2, 2016; Chicago, IL, USA; Chicago Cubs fans celebrate after game seven of the 2016 World Series against the Cleveland Indians outside of Wrigley Field. Cubs won 8-7. Mandatory Credit: Patrick Gorski-USA TODAY Sports

Ding dong, the goat is dead! The Chicago Cubs ended the longest drought in American sports and captured the World Series for the first time in 108 years. It didn’t come easy as the Cubs were pushed to the limit and then some through the MLB postseason.

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The Cubs had their chances to break their drought a few times in the last few decades, but for one reason or another, they failed to get it done. It wasn’t until Tom Ricketts bought the team and hired Theo Epstein did the Cubs get the right pieces in place to finally bring the World Series back to the North Side.

Theo came in with a plan and executed it to perfection. He told us on the day he was hired exactly what he was going to do like a prophet. After breaking curses in Boston and Chicago, Theo might be closer to a baseball god.

Things just seemed to break right for the Cubs the last couple of seasons. Just a couple of years removed from losing 100 games, Joe Maddon became available and seemed like the perfect trigger man to execute Theo’s plan on the field. The Cubs seemed to arrive a year early last season, but failed to close the deal as they got swept out of the playoffs in the NLCS at the hands of the New York Mets.

Maddon and the Cubs were considered the frontrunners for a title from the start of spring training. Rather than shying away from it, they “embraced the target” and came out with shirts that said “TRY NOT TO SUCK”. Mission accomplished. 103 wins in the regular season and a World Series title in the books. 108 years of waiting and futility washed away with a champagne and beer shower.

The arrow remains pointed up for the Cubs, who still have a young core of players and have the look of the 2010 Blackhawks. Time will tell if this is a one-and-done or the start of a dynasty.

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