Top 15 Worst Moments In Chicago Cubs History

There is always excitement and optimism surrounding the Chicago Cubs when they start their season. Chicago fans are ecstatic that winter is over and the joy of going to Wrigley Field to enjoy a ball game is right around the corner. However, that optimism usually lasts about half a month before the realization that the Cubs are the Cubs sinks in like a Greg Maddux two-seam fastball.

The Cubs floundering almost every summer is something that North side baseball fans have gotten used to, as well as dramatic heartbreaking losses on the rare occasions the team was good.

Well, the Cubs are predicted to win it all this season and the optimism at Addison and Clark has never been higher. The organization has gone through a complete overhaul under team president Theo Epstein and have the talent in-house and under contract for a decade long run of contention. It seems assured that the 108 year World Series drought is due to expire any year now.

So, before the Cubs win the World Series and ruin it for all the haters who love to see them and their fans suffer, lets take a look back at the worst moments in the history of the organization. The list had plenty to choose from, but these are the top 15 worst moments in Cubs history.

Continue scrolling to keep reading

Click the button below to start this article in quick view

Start Now

15 Sammy Sosa and the Corked Bat incident 

via youtube.com

For a slugger that smashed a Cubs record 545 homers with the team. you'd expect Sammy Sosa to be beloved by Cubs fans everywhere. However, Slammin' Sammy has created a cloud around his legacy with numerous questionable decisions. When he lost a briefcase with $20,000 in it in a hotel lobby. Or choosing to forget how to speak English at the Senate hearings on PEDs in baseball. Or blasting irritating music with his boombox in the locker room. But, the day it was discovered the Sammy Sosa aura was only a facade and possibly questionable was when his broken bat exploded all over the infield versus the Marlins. The umpires recognized that the bat had been tampered with and filled with cork. as it was splintered on the infield. Sosa denied any culpability claiming he accidentally used a batting practice bat. But, that didn't matter to MLB officials who suspended him for seven games, even though none of his other 76 bats x-rayed were tampered with.

14 Babe Ruth Takes the Mound in 1918 World Series

via en.wikipedia.org

As most know, Babe Ruth began his career as a dominant pitcher for the Boston Red Sox. And the behemoth was the difference in the World Series upset in six games over the mighty Cubs. The heavily favored Cubs won nine more games than the Red Sox, despite having only played 129 in the shortened 1918 regular season due to World War I. The upset began when Babe tossed a six-hit shutout to nip the Cubs 1-0 in Game 1. It came to a head when he added eight innings of two-run ball in Game 5. The Babe hammered a two-run triple in Game 5 to give him as many RBIs as runs allowed in the Series. His two wins, 1.06 ERA and 2 RBI would've won the World Series MVP if it had existed yet.

13 The Lee Elia Tirade

via wgnradio.com

In one of the most embarrassing tirades in the history of American sports, Cubs manager Lee Elia was recorded directing a profanity laced rant at heckling fans that gave management no other option but to fire him. It was April 29th, 1983 and the Cubs had just lost a one-run game to the Dodgers. Elia was fuming over the lack of support from the few people that were in the stands and from the booing and heckling of his players. He spewed venom at Cubs fans, mocking them that they didn't have jobs and other stereotypes for three full minutes. Radio veteran Les Grobstein recorded the infamous soundbite of Elia's.

12 Cubs "Rotate Coaches"

via cemeteryguide.com

In December of 1960, Cubs Owner P.K. Wrigley announced that the team was going to do away with having a manager, and instead, was going to use a rotation of different coaches throughout the season. The experts ridiculed the idea and they were right. Wrigley's contention that it was better for players to discern wisdom from eight men instead of one backfired with everything else that could go wrong with rotating the 'head coach.' The Cubs brought in eight men to rotate from the major league club to the minor league teams, with all of them taking turns to be in charge. However, the coaches would never help out the acting head coach, leaving him to fend for himself. The differing lineups and style of play resulted in two of the worsts seasons in franchise history. After going 64-90 in 1961, they dropped to 59-102 in 1962. Only the expansion Mets, who lost 120 games, were worse.

11 James Loney Smashes NLDS Grand Slam

via dodgersnation.com

The Cubs' organization was reminded over and over again before the 2008 season started that it had been 100 years since their last World Series championship in 1908. Coming off a playoff appearance in 2007 ,the team was intent on having an historic season. And they did, during the regular season. The Cubs won an NL high 97 games and strutted into the NLDS with hopes of taking care of the 84-78 Dodgers in front of a rowdy Wrigley Field crowd. Their early 2-0 lead did nothing but add to the delirium. But, after James Loney, with only 99 career homers, smashed a grand slam in the 5th inning of Game 1 to give the Dodgers a 4-2 lead, the fans went silent. A pall came over the Wrigley crowd as Loney circled the bases and a feeling of inevitability came spread through the stands and into the dugout. The Cubs felt it too. They never scored again in the game and then proceeded to hand Game 2 to LA by committing four errors. The best team in the NL was swept out of the playoffs in Game three with another meager effort that all started with the Loney Grand Slam.

10 Lou Brock Trade

via bleedcubbieblue.com

This is a moment that must've kept the Cubs' GM at the time, John Holland, up at night until his death. On June 15th, 1964 he made a six-player deal with the Cardinals with Lou Brock and Ernie Broglio being the centerpieces of the deal for each team. Many pundits thought the Cubs had gotten the better end of the deal at the time because Brock had been a disappointment in Chicago and Broglio was coming off an 18-win season with a sub 3.00 ERA. But, what Holland didn't know was that Broglio had his ulnar nerve reset before the season and that Brock was going to break out. Broglio fell on his face, going 7-19 for the Cubs and was eventually out of baseball by 1966. Brock, however, went on to a HOF career and helped his new team immediately. He batted .348 in his first year with the Cardinals and helped them win the 1964 World Series. He ended up with 3,023 career hits and 938 stolen bases while helping the Cardinals win two World Series and turned this into one of the most lopsided trades in MLB history.

9 Daniel Murphy Kills Cubs 

Dennis Wierzbicki-USA TODAY Sports

When Daniel Murphy stepped into the batter's box in Game 1 of the 2015 NLCS, it was over for the Cubs. With the Cubs riding an emotional wave of winning the Wild Card Playoff Game and then beating their bitter rivals, the Cardinals, in the NLDS, everything looked great for the Cubs who had beaten the Mets in all seven of their games in the regular season. Well, Murphy didn't want the Cubs to keep their confidence and he continued his home run deluge. He smashed a Jon Lester pitch for a tater to give the Mets a first inning lead that would boost them to a Game one victory. Murphy's heroics continued as he hit .529 for the series, with six runs, six RBI and a homer in each of the four games of the Mets' sweep.

8 Tigers Win World Series in Walk-off

via catalog.scpauctions.com

The heartbreaks that Cubs fans have dealt with goes back a long time, with their loss in the 1935 World Series to the Tigers as one of their most agonizing ones. They lost the series in six games, but they could have easily won Game 6 and forced a deciding Game 7 and could have sent Lon Warneke to the mound. Warneke had already won two games in the series. Instead, the Cubs blew a 3-2 lead in Game six and headed to the 9th knotted up at 3-3. Stan Hack smacked a lead-off triple to start the ninth inning for the Cubs, but was stranded there by Tigers starter Tommy Bridges. Wasting the Hack triple came back to burn the Cubs in the bottom half of the inning as Goose Goslin hit a bloop single just over the outstretched glove of future HOF second baseman Billy Herman. The ball wasn't hit hard, but with two outs it gave Mickey Cochrane enough time to race home and beat the throw from Chuck Klein for the GW run. The Cubs won 21 consecutive games in September that season to rally and win the NL Pennant, only to face disappointment.

7 Babe Ruth Calls Shot

via sportingnews.com

Oaky, there is very little physical evidence to prove that Babe Ruth actually pointed to the centerfield bleachers after taking two called strikes from Cubs pitcher Charlie Root before preceding to smack a home run to the same bleachers he was pointing. There is a film of him gesturing towards the Cubs' dugout and then at Root, followed by his prodigious blast in Game three of the 1932 World Series. A series the Yankees would sweep despite the fact the Cubs held the lead in every game. But, the lowest moment of the series was when Ruth answered the catcalls from Cubs players in the dugout with his own smack talk, gestures and then home run. The home run gave the Yankees a lead they wouldn't relinquish and a fable that will live as long as there's baseball. And for Cubs fans, it's another moment to add to their misery.

6 Leon Durham Commits Error Versus Padres

5 A Black Cat Streaks Across Their Path

VIA aroundthehorntalk.mlblogs.com

There are many experts that say the 1969 Cubs are the best team in the history of the divisional era that didn't make the playoffs. While that will be impossible to prove, that statement carries a lot of weight considering their roster had HOFers like Ernie Banks, Billy Williams, Fergie Jenkins and Ron Santo on it. They were having the best season for a Cubs team since 1945 during August of that season when they had an 8.5 game lead over the Cardinals and a 9.5 game lead over the Mets. However, on September 9th, their lead over the Mets was only 2.5 games as they went to Shea Stadium to play a double header. During the first game, a black cat walked on the Cubs' dugout, around Ron Santo in the on-deck circle and then back to the Cubs' dugout. Whether you're superstitious or not, there's no debating that the Cubs lost both ends of that double header to leave Shea with their lead cut to half a game, and they wouldn't hold on to it. The collapse by the 1969 Cubs is one of the most infamous in baseball history and no moment is worse that year than the black cat moment.

4 Cubs Blow 8-0 Lead and the 1929 World Series

via vintagecubbies.blogspot.com

The 1929 Cubs are one of the best clubs in team history, yet they'll be remembered for their collapse during the 1929 World Series. The loaded Cubs' roster had a preposterous .645 winning percentage on the way to taking the NL pennant and were matched up against the mighty Connie Mack Philadelphia A's. The A's were up 2-1 in the series during Game 4, but the Cubs were in total control and looking like they would even the series at 2-2. They had an 8-0 lead going into the bottom of the 7th inning that resulted in a 99.7 win probability. But, this is the Cubs and numbers should be thrown out. If only the Cubs could get the next number thrown out. The A's scored 10 runs in the bottom of the frame to take a 10-8 lead and squelch any hopes by the Cubs of winning that series. And of course, since this is the Cubs, an inexplicable play happened to cost them the game. HOFer Hack Wilson lost a routine fly ball in the sun that turned into an inside-the-park three-run homer for Mule Haas.

3 Ken Hubbs Dies in Plane Crash

via bleedcubbieblue.com

There are many dismal moments in the history of the Cubs, but nothing as tragic as the day Ken Hubbs died in a plane crash in Provo, Utah on February 15th, 1964. The 22 year old was the 1962 NL Rookie of the Year while becoming the first rookie to ever win a Gold Glove as he manned second for the Cubs. He handled a then record 418 consecutive chances without an error that season and had the baseball world crooning over his athletic abilities. He could've played QB at Notre Dame or point guard for John Wooden's UCLA Bruins, but the native Californian wanted the quickest route to the bigs, so he took the $50,000 signing bonus to join the Cubs' organization. He made it to the bigs within two years and played well enough to have Cubs owner Phillip Wrigley rip up his contract and double it his rookie season. We'll never know what the Cubs lost when the 22 year old died in 1964, but Sports Illustrated speculated that there would never have been a 1969 collapse if Hubbs was partnered with Banks, Santo and Williams in their lineup.

2 The Steve Bartman Incident

via zerofiltered.com

Never in the history of American sports has one innocent man ever been more vilified that Steve Bartman was for his role in the Cubs' collapse during Game 6 of the 2003 NLCS versus the Marlins. The youth league baseball coach had his earbuds in and was enjoying the Cubs 3-0 8th inning lead while watching the game in the first row down the left field line. Slap hitter Luis Castillo hit a pop fly into the left field foul territory where Bartman was sitting. Left outfielder Moises Alou had a read on the ball and leapt up against the wall to make the catch, Instead, Bartman got in the way and redirected the ball, letting it fall harmlessly to the ground. Immediately, Alou threw a hissy fit and started screaming at the confused fan. The fans in the section joined in on the attack with their own screams and threats at the bewildered youth coach. But, instead of realizing that the play didn't ruin the Cubs and only put Castillo in a full-count, they folded like bed linens. The obviously flustered pitcher, Mark Prior, walked Castillo, then the real mistake happened. Alex Gonzalez misplayed a routine double-play ball that would've ended the inning with the Cubs up 3-0. The E6 opened the floodgates and the Marlins scored eight runs in the inning and took Game 6 and eventually Game 7 as well. After the game venom was spewed at Bartman when the real culprits were Alou for going ballistic, Prior for losing his poise, Alex Gonzalez for the error and Cubs' manager Dusty Baker for not getting a relief pitcher up in the bullpen. He claimed he didn't want to add to the Marlins' momentum by getting a reliever up.

1 Cubs Get Hexed by Curse of the Billy Goat

via billygoattavern.com

Whether or not this curse is real is as big an argument as to what the exact curse was in the first place. Legend has it that Billy Goat Tavern Owner, Billy Sianis, put a curse on the Cubs after being told to leave Game 4 of the 1945 World Series at Wrigley because the goat he brought to the game was so odoriferous that the surrounding fans complained to have it removed. Then Sianis, supposedly, said, "Them Cubs aren't going to win no more." We know Sianis was asked get the smelly animal out of the park and that he complained for years that he had bought a ticket for his four-legged friend. However, we can't be sure of the exact curse he put on the team because he consistently changed his statement on what he did. What we do know is that the Cubs never won another World Series, nor after the incident have ever been back to test their fate. And this curse has been brought up every time the Cubs have a quality ball club and were vying for postseason play. It's just another mental hurdle that Cubs players have to overcome to eventually stamp out their World Series drought.

More in MLB