Getting your Trinity Audio player ready...

Chicagoans are familiar with disappointment.

“There’s always next year,” was the motto for generations of Cubs fans who waited 108 years between the team’s last two championships.

Yet, there have also been times when it appeared that Chicago was ready for its moment in the sun — before suddenly, unexpectedly stumbling.

More Top Picks Best Green Light Therapy Lamps For Migraines

Those are the disappointments that really hurt.

This week marks 56 years since then-Mayor Richard J. Daley unveiled a gift to the city from Pablo Picasso. The octogenarian Spanish artist had been wooed by architects of the Civic Center (now named for Daley) to create a focal point for its plaza.

“Although we were willing to experiment along many lines in other situations, we wanted the sculpture to be the work of the greatest master alive,” said William E. Hartmann, senior partner in Skidmore, Owings & Merrill, in 1967.

On Aug. 15, 1967 — after a performance by the Chicago Symphony Orchestra and a poetic tribute recited by Pulitzer Prize winner Gwendolyn Brooks — about 50,000 Chicagoans got their first glimpse of Picasso’s present.

Mayor Richard J. Daley and Architect William Hartmann unveil Chicago's Picasso sculpture on Aug. 15, 1967.
Mayor Richard J. Daley and Architect William Hartmann unveil Chicago’s Picasso sculpture on Aug. 15, 1967.

“Oh mommy, it’s terrible,” a young Bob Wadell told his mother.

“I hope it’s a phoenix,” she responded.

“It’s hideous, it means nothing, it’s like a cow sticking out its tongue at Chicago,” an elderly woman told everyone within ear shot.

Others suggested the 50-foot steel sculpture was a bird, a horse, a Viking ship, a baboon or a modernistic representation of Picasso’s dog. Nobody really had an answer — especially since Picasso himself didn’t show up for the ceremony.

The Tribune summed up the untitled masterpiece like this: “For decades, possibly for generations, Chicagoans will dispute about this huge semi-abstract head of a woman — or is it something else? — which will be like a brooding presence in the center of the city. It will be derided, defended, laughed at, and — who knows? — maybe eventually loved.”

And perhaps that’s the key to getting over disappointment — acceptance. Though once considered a white elephant, who can imagine Daley Plaza now without the Picasso?

Here’s a look back at big bummers in Chicago history. Some, like the Picasso, became easy to accept over time. Others still sting.

1919: 8 White Sox players fall from grace and are forever marked the ‘Black Sox’

Attorneys and a few White Sox players pose during the Black Sox trial of 1921. White Sox player’s in the back row are George “Buck” Weaver, center, Oscar “Happy” Felsch, second from right, and Anthony “Chick” Gandil. White Sox shortstop Charles “Swede” Risberg is second from right, in the front row.

The 1919 White Sox — considered by some baseball historians as one of the greatest teams ever to take the field — were heavy favorites to beat the Reds in the World Series. But in the best-of-nine series (Major League Baseball decided to expand from the best-of-four format due to postwar demand), the Reds dominated.

There had been rumors and reports that the fix was in, and indeed the Sox’s performance was suspect. A year later, eight White Sox players were charged with throwing the World Series. In 1921, all were acquitted by a jury that deliberated just 2 hours, 47 minutes.

A day after their acquittal, however, baseball Commissioner Kenesaw Mountain Landis ruled the players allegedly involved — Joe Jackson, Eddie Cicotte, Oscar Emil Felsch, Chick Gandil, Frederick William McMullin, Swede Risberg, Buck Weaver and Lefty Williams — would be banned for life from organized baseball.

Aug. 15, 1967: Picasso unveiled — ‘It’s hideous!’

On Aug. 15, 1967, Mayor Richard J. Daley unveils Pablo Picasso s 162-ton, 50-foot-high steel gift to the people of Chicago, the Daley Plaza sculpture now simply known in the city as the Picasso.
On Aug. 15, 1967, Mayor Richard J. Daley unveils Pablo Picasso s 162-ton, 50-foot-high steel gift to the people of Chicago, the Daley Plaza sculpture now simply known in the city as the Picasso.

Just after noon, Mayor Richard J. Daley pulled a cord attached to 1,200 square feet of blue-green fabric, unwrapping a gift “to the people of Chicago” from a Spanish artist (Pablo Picasso) who had never visited — and had shown no previous interest in — the city.

It was the first monumental outdoor Picasso in North America — it was also Daley said at the unveiling: “We dedicate this celebrated work this morning with the belief that what is strange to us today will be familiar tomorrow.”

Col. Jack Reilly, the mayor’s director of special events, immediately urged removal of the sculpture. Ald. John J. Hoellen went further, recommending that the City Council “deport” the piece and construct in its place a statue of “Mr. Cub … Ernie Banks.”

Yet, it grew on us. The name-brand quality of the sculpture inspired other commissions — from Alexander Calder, Marc Chagall, Joan Miro, Claes Oldenburg and Henry Moore — that found easier acceptance among Chicagoans.

Jan. 26, 1986: ‘Sweetness’ doesn’t score in Super Bowl XX

Bears running back Walter Payton shouts encouragement to his teammates during Super Bowl XX.
Bears running back Walter Payton shouts encouragement to his teammates during Super Bowl XX.

Walter Payton didn’t score in the Super Bowl, but the Refrigerator did. Just think of that a minute.

Coach Mike Ditka didn’t feel it necessary to apologize for leaving Payton out of the Bears’ Super Bowl scoring parade. “It’s unfortunate Walter didn’t get a touchdown, but Walter’s contribution … nobody has to talk about it,” he said after the game. “The Patriots keyed their whole defense on him.”

April 21, 1986: Al Capone’s vault — empty

Excavators Tom Kasper, left, and Dan Constantino dig out the sand fill after the walls into vaults at Chicago's Lexington Hotel, linked to mobster Al Capone, were blasted away during a TV telecast, April 21, 1986. The only thing the dig turned up was an old liquor bottle.
Excavators Tom Kasper, left, and Dan Constantino dig out the sand fill after the walls into vaults at Chicago’s Lexington Hotel, linked to mobster Al Capone, were blasted away during a TV telecast, April 21, 1986. The only thing the dig turned up was an old liquor bottle.

The most exhilarating live television event of 1986 was the Chicago Bears winning Super Bowl XX, for some. For others, it was a two-hour broadcast from a basement.

Spoiler alert: The early experiment in unscripted programming was one of the most fascinating busts in Chicago history. “The Mystery of Al Capone’s Vaults” host Geraldo Rivera may have walked out of the hotel empty-handed, but the show’s incredible ratings delivered him a long-term talk show deal.

April 13, 1992: Great Chicago Flood paralyzes downtown

Pedestrians step over hoses used to pump out flood water from buildings at the intersection of State and Madison Streets. Scenes like this on downtown Chicago streets were commonplace in April 1992, due to massive basement and sub-basement flooding caused when crews punctured a century-old freight tunnel located underneath the Chicago River.
Pedestrians step over hoses used to pump out flood water from buildings at the intersection of State and Madison Streets. Scenes like this on downtown Chicago streets were commonplace in April 1992, due to massive basement and sub-basement flooding caused when crews punctured a century-old freight tunnel located underneath the Chicago River.

The city’s failure to fix cracks in underground freight tunnels leads to the the Great Chicago Flood and $1 billion in damages. Those who were there vividly remember that spring day when 124 million gallons of water from the Chicago River flowed into the city’s maze of underground freight tunnels and building basements, turning the Loop into a ghost town.

Oct. 14, 2003: ‘The Fan’ blamed for Cubs postseason loss

Cubs left fielder Moises Alou's arm is seen reaching into the stands, at right, unsuccessfully for a foul ball against the Florida Marlins, as fan Steve Bartman deflects the ball, at top, in the eighth inning during Game 6 of the National League championship series on Oct. 14, 2003 at Wrigley Field in Chicago.
Cubs left fielder Moises Alou’s arm is seen reaching into the stands, at right, unsuccessfully for a foul ball against the Florida Marlins, as fan Steve Bartman deflects the ball, at top, in the eighth inning during Game 6 of the National League championship series on Oct. 14, 2003 at Wrigley Field in Chicago.

A 26-year-old spectator seated in Section 4, Row 8, Seat 113 and initially identified in the media as The Fan reached over the Wrigley Field railing for a foul fly in the top of the eighth inning of the sixth game of the National League Championship Series, a game the Cubs were leading 3-0 with just five more outs to clinch their first World Series berth since 1945. The Fan deflected the ball out of the mitt of Cubs outfielder Moises Alou. The play preceded a Rube Goldberg sequence of Cubs’ calamities, including a botched double play grounder by Alex Gonzalez and a meltdown by Mark Prior and the bullpen.

The fan was mercilessly harassed by Cubs’ fans after the incident and the Cubs fell apart, going on to lose that game and the next game. After 14 years and thousands of replays, the Cubs awarded him with a 2016 World Series ring, hoping to create closure on what they called “an unfortunate chapter of the story that has perpetuated” over the years.

Perhaps the most remarkable storyline in the years since the 2003 game is that this fan, Steve Bartman, has managed to remain private.

Dec. 4, 2008: The city’s lopsided parking meter deal

Chicago Mayor Richard M. Daley talks about a deal for a long-term lease of Chicago's parking meter system at City Hall on Dec. 2, 2008.
Chicago Mayor Richard M. Daley talks about a deal for a long-term lease of Chicago’s parking meter system at City Hall on Dec. 2, 2008.

Then-Mayor Richard M. Daley strikes a deal to close a budget shortfall — the city gets a paltry $1.16 billion upfront in return for a 75-year lease of Chicago’s paid street parking system to Chicago Parking Meters (CPM). Nearly all of the one-time windfall would be spent by the time Daley handed over the reins to Mayor Rahm Emanuel. Meanwhile, the contract required the city to drastically raise rates on behalf of the company.

Chicago’s inspector general confirmed in 2019 that the city had sold out for far less than the lease’s value. A report by Bloomberg Business said CPM stood to earn about 10 times what it paid over the life of the contract. “Any way you slice it financially, Chicago got taken to the cleaners,” the Tribune Editorial Board said earlier this year.

Oct. 2, 2009: Chicago loses Rio Olympics bid

Emily Harbaugh, from left, 18, Martha Willis, 20, and Kristen Glogowski, 19, carry signs that reflect the glum mood at Daley Plaza party after Chicago's ouster on Oct. 2, 2009. The city got only 18 out of 94 votes.
Emily Harbaugh, from left, 18, Martha Willis, 20, and Kristen Glogowski, 19, carry signs that reflect the glum mood at Daley Plaza party after Chicago’s ouster on Oct. 2, 2009. The city got only 18 out of 94 votes.

Despite an appearance by then-President Barack Obama at the final presentations, Chicago’s candidacy to host the 2016 Games landed with a thud. At exactly 10:32 a.m., then-IOC President Jacques Rogge forever became part of the city’s sports landscape with a stunning declaration: “The city of Chicago, having obtained the least number of votes, will not participate in the next round.” Given Chicago’s status as the favorite, this was the equivalent of a No. 1 seed being ousted by a No. 16 on the first day of March Madness. A shocker.

Mounting Chicago’s bid was an expensive but privately funded endeavor. Nearly $76 million was raised from donors, who also kicked in $16 million worth of goods and services. But it left a pricey legacy for taxpayers.

Oct. 4, 2014: Great Chicago Fire Festival fails to ignite

A singed but not burned floating mansion prop sits at the Michigan Avenue Bridge on Oct. 5, 2014 . It and two other displays failed to ignite the night before during the Great Chicago Fire Festival.
A singed but not burned floating mansion prop sits at the Michigan Avenue Bridge on Oct. 5, 2014 . It and two other displays failed to ignite the night before during the Great Chicago Fire Festival.

The idea for a Great Chicago Fire Festival dated back to Chicago’s failed Olympic bid in 2009, when it was conceived as part of the ceremonies, a Redmoon Theater spokesman told the Tribune. But — like the announcement of the city’s bounce from Olympic contention — the festival fizzled. Thousands of spectators lined the Chicago River to watch floating mock-ups of Victorian houses become engulfed by flames — a la the Great Chicago Fire of 1871 — but the buildings failed to ignite. After several failed attempts to light the fires, the spectacle’s crew moved on to the fireworks finale.

Jan. 6, 2019: ‘The Bears season’s going to end on a double doink’

Bears kicker Cody Parkey reacts after missing the potential game-winning field goal in the final seconds of the fourth quarter against the Eagles at Soldier Field on Jan. 6, 2019.
Bears kicker Cody Parkey reacts after missing the potential game-winning field goal in the final seconds of the fourth quarter against the Eagles at Soldier Field on Jan. 6, 2019.

With 5 seconds left in the Bears’ first playoff game since the 2010 season, Cody Parkey’s 43-yard field-goal attempt bounces off the left upright, hits the crossbar and bounces out. “Oh, my goodness,” NBC’s Cris Collinsworth says. “The Bears season’s going to end on a double doink.” (Six of Parkey’s misses the previous season hit an upright.) The Eagles win 16-15 in the wild-card round of the NFL playoffs.