The Top Five Worst Sports Years in Chicago Sports History

The past couple years have not been kind to Chicago sports fans.

Sure, the White Sox, Cubs, Blackhawks, and Bears each made their respective league’s expanded playoffs. However, each team lost in their opening round (NOTE: No, we’re not counting the Blackhawks’ preliminary round victory over Edmonton).

Things haven’t been good, they haven’t been awful, but they’ve most certainly been ‘ehhhh?’

We’re on the verge of the Bulls and Blackhawks both missing the playoffs…again.

The Cubs are meandering the wasteland of baseball’s .500 teams.

And the Bears are going to try to make another first-round quarterback work. (We think it will. Oh, and Aaron Rodgers? If you’re reading this? Please leave Green Bay)

Our city’s solace? Those feisty White Sox! Yes, the Pale Hose are hot. Shoot, the AL Central may be their own title palace by early September.

So, while things aren’t necessarily awful, they’ve certainly been better. If you’ve been a fan of Chicago sports for some time, you’ve seen much, much worse.

Let’s rank the top 5 worst sports years in Chicago professional sports history.

(NOTE: We’re taking the traditional five squads; Bears, Blackhawks, Bulls, Cubs, and White Sox. Much love to the Sting (RIP), Fire, RedStars, and Sky.)

5: 1969

If you’re young, you might be surprised to note that the Chicago Bears were consistently competitive from their inception until the mid 1960’s. The Cubs were in the National League race regularly from the late 20’s until 1945. Once the Cubs cooled, the White Sox were regular challengers for the American League crown throughout the 50’s and 60’s.

That’s why you won’t find a single year in our top 5 before 1969.

1969 is normally linked to the moon landing, Woodstock, and the collapse of the Chicago Cubs. How can this year make the top 5 if the Cubs won 90 games?

The collapse, combined with the rather anemic results throughout the remainder of the city, make 1969 a worthy contestant.

The year started with the city’s newest professional basketball franchise, the Bulls, missing the playoffs for the first time in their three-year existence. Red Kerr had left to run the expansion franchise in Phoenix. The Bulls scrambled to grab a little-known coaching commodity from Weber State by the name of Dick Motta. 1968-69 was a learning season for Motta and his squad that resulted in a 33-49 season. The core of Bob Love and Jerry Sloan was still in its youth, and years away from contention.

While the Bulls struggled, their Chicago Stadium counterparts, the Blackhawks, missed the playoffs for the first time in 11 years. The NHL expansion had pushed the Original Six franchises into one division. The Blackhawks finished 34-33-9 finishing dead last in the ‘experienced’ Eastern Division. The Hawks were between Hall of Fame goaltenders Glenn Hall and Tony Esposito. Denis DeJordy was in net for the year, and the Hawks paid the price by finishing 8th of 12 teams in Goals Against Average.

The White Sox? The Sox were in a tailspin.

While the Cubs took the headlines of the summer racing out to a 77-45 start, the south siders still reeled from their collapse during the final week of ’67. Luis Aparicio was getting older. Younger players like Pete Ward and Ken Berry hadn’t developed into the players the Sox expected. Pitching was always the Sox standard, but in ’69 the old stalwarts began to falter. It was the first time that Joe Horlen, Tommy John, and Gary Peters combined to finish with losing records. Worse? None were able to log an ERA under 3; seemingly a tougher achievement with the lowering of the mound that same year.

White Sox bats were always a problem; certainly not helped by the spacious ‘confinements’ of old Comiskey Park. By ’69 they had tanked to more than 20 points below the league average. A team that perennially contended in the American League throughout the 50’s and 60’s would fall through it’s second consecutive 90 loss season; the first time since 1950.

The Cubs collapse in late August/early September coincided with the start of Bears season. The Bears had been checking to see if Gale Sayers could return to his old form after a devastating knee injury. What they didn’t take into consideration was the likely need for a quarterback (see: Bears History) to drive their success.

The 1969 Bears set a franchise standard for ineptitude going 1-13. The Bears finished dead last in offense. Dead last in passing yards. The team featured two hall of fame starters in Gale Sayers and Dick Butkus and could only manage two wins. The Bears rotated between Jack Concannon, Bobby Douglass, and Virgil Carter at quarterback. The carousel did not pay off, and most Bears fan got off.

The NFL played only 14 games back then. The Bears failed to score more than 7 points on six different occasions. Woof!

By the end of 1969, Chicago fans were happy to see that the Blackhawks would be surging in December, and carry their success into the next year.

4: 1976

1976 almost gets a pass, because for the first time since 1968 the Bears finished with a .500 record. Walter Payton emerged as a top running back in the league, and coach Jack Pardee had turned the Bears into a competitive football team. Pardee won Coach of the Year with his team going 7-7 against a brutal schedule that featured the Raiders, Rams, and Cowboys.

What made 1976 so bad was the combination of ineptitude from the boring Jim Marshall-led Cubs, the implosion of the Bulls, the sudden demise of the Blackhawks, and a White Sox team that refused to build on earlier success from the decade.

The Cubs in ’76 weren’t a complete disaster. Bill Madlock won the NL batting crown, Rick Monday hit 32 homers, and the combo of Reuschel/Burris was a feasible aggressor against many lineups. Unfortunately, the Cubs infield could not hit outside Madlock. And that’s an understatement.

Pete LaCock, Manny Trillo, and Mick Kelleher combined to hit a whopping 12 home runs in over 350 games played. They combined to hit around .230; providing little speed and mediocre defense (outside of Trillo).

While the Cubs ‘Slumber of the 70’s’ continue in ’76, the White Sox put forth one of their worst efforts in franchise history. The White Sox of ’76 were so bad it forced the organization to do a complete re-haul in their efforts for ’77.

There were talented players like Chet Lemon and Ralph Garr, but nothing on the field could stop the horrific pitching exploits of the White Sox staff.

The Sox finished dead last in team ERA at 4.25 and a WHIP of 1.4. After years of being known for their pitching and defense, the Sox had hit the rewind button to the dark days of the 1930’s.

The Blackhawks had also begun a slide in 1975 that wouldn’t end until 1980. The Blackhawks would set a record with 18 straight playoff losses. The only reason the Blackhawks made the NHL playoffs in 1976, was because the league required the division winner to make the playoffs. The Hawks went 32-30-18 with an aging Stan Mikita and an anemic offense that finished 12th of 18 teams in ‘Goals For’.

The Hawks’ post-Bobby Hull dive had slowly moved the team from contender to pretender. The year after Hull left, the Hawks still made the Finals in ’73. But after getting 100 points in ’74, the Hawks spiraled to mediocrity by ’76.

The Hawks were promptly destroyed in the first round of the playoffs by the eventual Stanley Cup Champion Montreal Canadiens. The Hawks scored a whopping 3 goals in 4 games.

The Bulls of ’76 are really what launches this sports calendar year into the top 5. Dick Motta’s Bulls were a soap opera in ’76 due to a couple items: Jerry Sloan got hurt midway through the year (an injury that led to his retirement), Norm Van Lier kept have run-ins with the league/management, and one of the heroes of the Bulls’ 75 run, Nate Thurmond, was traded to Cleveland.

The Bulls never recovered from their double digit fourth quarter lead in Oakland the previous year. The Bulls were a quarter away from reaching the NBA Finals for the first time in franchise history before imploding against the Golden State Warriors. The hangover stretched into the fall of ’75, and the Bulls staggered to a 24-58 season. Motta was fired, and the goodwill established through the earlier part of the decade was now gone.

3: 1978

The 1978 sports calendar had many similarities to 1976.

1977 was a respite during a tumultuous time in Chicago sports. The Bulls and Bears both made late runs to the playoffs. Heck, even the Cubs and White Sox got off to hot starts (though, both eventually led in August/September crashes).

Badger’s squad had a thrilling run to the playoffs in ’77 by winning 20 of their final 24 games dubbed as the ‘Miracle on Madison’. In ’78, the thought was big man Artis Gilmore could center the offense to another strong finish in the ‘big-man-centered league’ of the 1970’s.

Norm Van Lier was getting older. Bob Love was gone. The Bulls finished five games back of the final playoff spot.

The Blackhawks’ woes continued through the late 70’s. The NHL’s new playoff format required that all top two division finishers get an automatic berth. The Hawks only had the 8th best record out of 18 teams. Outside of Ivan Boldirev, there wasn’t much offensive talent on the team anymore. The high-flying Hawks of the early 70’s were gone. Bob Pulford was now behind the bench trying to restore the glory years, but the Hawks’ focus on defense turned the squad into a dry offensive unit. The Hawks finished 12th of 18 NHL teams in scoring and were swept by the Bruins in the first round.

Baseball? After the thrill of the first half of 1977, the Cubs and White Sox returned to their losing ways in 1978.

The ’78 Cubs, like many Cubs teams of the late 70’s, got off to a decent start. They actually stayed in contention for a good portion of the year until…wait for it…a collapse took place! The Cubs were 66-62 and only 2 ½ back as late as August 27th. The Cubs proceeded to go 11-20 in their next 31 and ‘that was that’, as they say.

The White Sox tried to carry fire over from their ’77 season. The South Side Hit Men were the first Sox team in quite some time to carry the lumber. The power numbers faded in ’77, but the team still hit over the league average. The hits, unfortunately, came from the White Sox pitching staff. The Sox averaged the 12th best league ERA at 4.21. The Sox faded to a 71-90 finish.

Oh, and how would the Bears fare after their miracle finish in 1977? The Bears ran off six straight victories to conclude a 9-5 playoff campaign in ’77. Hopes were high in ’78.

One of the men responsible for turning around the Bears, head coach Jack Pardee, had bolted to Washington for a ‘dream job’ of his after 1977. Neil Armstrong (not the man at the moon), took over the gridiron in ’78.

It was another solid year for Payton, the team’s best offensive weapon by a mile. The Bears started 3-0, but after losing tough games to perennial contenders Minnesota and Oakland, the Bears collapsed. The 3-0 start switched to an eight game losing streak. The Bears rallied to save face at 7-9.

The problem, like usual, was the passing game. The Bears were 27th of 28 teams in passing touchdowns. 26th of 28 teams in passing yards. Which is even more impressive when you consider they were playing from behind in most games. The Bears tried switching from Bob Avellini to Mike Phipps, and the result was the same. Payton provided 1,775 yards rushing and receiving. Avellini provided just 1,718 with his arm. Pretty astounding.

2: 1980

It’s tough to list 1980 on here considering the Blackhawks would finish 34-27-19. The Hawks swept the Blues in the first round before getting swept by Buffalo. Tony Esposito enjoyed a renaissance year leading the Hawks to a top 5 GAA.

It’s the baseball of 1980 that moved this into a top slot. The White Sox had this manager named Tony LaRussa (you may have heard of him). There were ingredients of the 1983 squad that were starting to flourish. Richard Dotson and LaMarr Hoyt entered the rotation. Harold Baines was showing flashes of the player he’d become. But the team was still a couple years away. Most notably, at the plate, where the White Sox hit only 91 home runs as a team.

The Sox started 22-15 and proceeded to go 40-73 over their next 103 games. A final week of wins kept their record semi-respectable.

The Cubs never got respectable in 1980. After the final month collapse of 1979 by Herman Franks, Preston Gomez’s tenure as Cubs manager began with an 11-6 start. It concluded with a 53-92 finish.

Like many Cubs teams of the time, there were a couple things you could hang your hat on: Bill Buckner won the batting title, Bruce Sutter was the league leader in saves. But the depth was non-existent. The Cubs were months away from their sale to the Chicago Tribune. Ownership throught a lineup featuring Mike Tyson, Lenny Randle, and Tim Blackwell would be able to compete with the Phillies and Pirates.  The Cubs would finish 10th in batting average, 10th in OBP, and 9th in Slugging out of 12 teams. They were 11th of 12 in ERA. They were truly an awful all-around team.

The Bears of 1980 came in with high hopes after their playoff season of 1979. Those high hopes dwindled quickly, en route to a 4-8 start. The Bears lost their opening game to Green Bay with the famous Chester Marcol blocked field goal run for a touchdown. Things did not get much better after that. The quarterback carousel was back. The Bears spent the year rotating between Vince Evans and Mike Phipps. Evans did give the team a thrilling come-from-behind victory on Thanksgiving against the Lions, and a memorable pounding of the Packers 61-7.

The Bears still finished another year dead last in passing yards, and 27th in passing touchdowns. Another year of Walter Payton was shot down the tubes.

The Bulls were in the midst of a playoff drought in 1980. ’80 would be the third straight year the Bulls would miss the playoffs.

Jerry Sloan returned as a coach, but the results did not improve. The Bulls had lost the draft coin flip for Magic Johnson, and wound up with the middling efforts of David Greenwood. The Bulls were trying to find some athleticism to surround Artis Gilmore and were continuously being shut out. The Bulls led the league in fouls, and were 21 of 22 teams in field goal percentage.

1: 1999

You can draw a line from the moment the Cubs were eliminated in the 1998 MLB Playoffs until you reach the White Sox 2000 baseball season. Inside this dateline, you’d see the worst calendar year stretch in Chicago sports history.

You can probably start in 1998, with the Bears going 4-12 in Dave Wannstedt’s swan song.

Michael Jordan announces his retirement shortly after the NBA lockout ends. In these empty months of late 1998, the Blackhawks flounder under Dirk Graham. At one point, they were 19-39-9 before finishing up 10-2-3. The Blackhawks had built up anger in the face by trading away Ed Belfour and Chris Chelios, and refusing to re-sign Jeremy Roenick. The franchise was slowly becoming a non-story in the city.

The Bulls were looking forward to rebuild in the post-Michael years. For those that remember, the 1998-99 Chicago Bulls were the worst Bulls team ever.

The worst.

You may find stats that show you otherwise.

You are wrong. For those of us that watched, nothing will come close to the pain of watching Mark Bryant and Kornel David.

There were holdovers from the championship years like Toni Kukoc, Ron Harper, Randy Brown, etc. But with no Jordan, no Pippen, and no Rodman it was a total joke. Tim Floyd looked out of place running a big city franchise. The result was a 13-37 team that couldn’t shoot and couldn’t defend.

The Cubs and White Sox entered 1999 with two different types of squads.

The White Sox were in the middle of the ‘These Kids Can Play’ campaign. Some elements were developing for the Sox while others weren’t coming on so quickly. There was definite young talent with Carlos Lee, Magglio Ordonez, Chris Singleton, Paul Konerko, and Ray Durham. The problem was that the Sox staff was very young and not solidified. The Sox had hung their hat on guys like Sirotka and Baldwin; which was fine. But the Jaime Navarro signing was hindering the Sox development. Navarro was a starter you could always depend on for 30 starts a year going back to his days with the Brewers and Cubs. His ERA ballooned to 6 in ’99. The White Sox team ERA in ’99 was 4.92, a full half run over the league average.

The Cubs had an older team that had made the playoffs in 1998, and were trying to repeat their magical 90 win effort from the previous year. They knew they’d head into the season short-handed; as rookie ace Kerry Wood would undergo surgery.

Gary Gaetti, Henry Rodriguez, Mickey Morandini, Kevin Tapani; it was a roster that was made to win the 1995 National League pennant.

The Cubs started 32-23 before their atrocious bullpen of Rick Aguilera and friends began to erode. Steve Trachsel went from being a hero in 1998, to a 5.56 ERA. The Cubs TEAM ERA was 5.27. Read that again.

What’s amazing about the ’99 Cubs is they got a 288/367/635 slashline from Sammy Sosa with 63 home runs and 141 RBI’s and still found a way to lose over 90 games. Gaetti couldn’t repeat his September of ’98 antics. Neither could Mickey Morandini. The Jeff Blauser signing was looking worse every day.

The Cubs hit a portion of the schedule where they gave up 75 runs over 5 games. That’s 15 runs PER game. They went from 32-23 to 56-87. A stretch of 24-54. They were still 46-47 on July 22nd before 10-40 over a 50 game span. 10-40.

The Bears were halfway decent at the start of 1999 due to the new dink and dunk offense of Gary Crowton that confused NFL defensive coordinators. The Bears were 3-2, but staggered to a 6-10 finish. It’s crazy to say this, but the team was generally competitive. Being competitive at that point in time was viewed as a positive. The horrors of Chicago sports wouldn’t end until the White Sox run in the summer of 2000, and for Cubs fans in Chicago, it mostly didn’t end until the Cubs surprise start in 2001 coupled with the Bears 13-3 season.

There’s probably another calendar year that you thought was worse! I’ve included the near-misses below.

Let’s hope that we’re not in the middle of one of those stretches right now. With Justin Fields, the White Sox, and some new additions for the Bulls…the future might finally look brighter.

Honorable Mention: 2000 (White Sox won division), 2002 (Blackhawks made playoffs), 2004 (Sox and Cubs were halfway decent), 2019 (All teams miss playoffs; sit around .500)

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