Chicago Cubs: The 10 Worst Moments In Team History

There is no team in all of pro sports that shares the heart-wrenching, disappointing history that the Chicago Cubs have.

As everyone who has ever watched a baseball game probably knows, the Cubs are 101 years removed from their last World Series title, and have not even played in the Fall Classic in 64 years.

What follows is my take on the ten worst moments in the history of the team that seems to be perennially "waiting til next year."

While it is difficult to compare what is worse when it comes to something such as trading away a future Hall of Fame outfielder versus a certain fan who couldn't just keep his hands to himself, i have done my best to put these in order.

Feel free let me know if I have excluded any moments, as there were certainly plenty to choose from.

No. 10: The First Night Game

Date: August 9th, 1988

While it was more or less an inevitability that the Cubs would get lights, and some Cubs fans may even consider this day to be one of the better moments in Cubs history, it still marked the end of an era, as Wrigley Field and daytime baseball always went hand in hand.

While the team still plays fewer night games than anyone else, baseball purists were strongly against anything but sunshine illuminating Wrigley Field. The was back when the lights were first constructed, and the decision was not met with unanimous support.

Strangely enough, the inaugural night game only made it three and a half innings before being rained out. A telling sign, and surely more than just a coincidence in the eyes of to those that were opposed to the lights.

No. 9: Sammy's Corked Bat

Date: June 3rd, 2003

On paper, 2003 was just another stellar season for slugger Sammy Sosa, as he launched 40 homers and drove in 103 runs, good for an eighth place finish in NL MVP voting.

The season was not all good for the slugger, however, as he earned himself a suspension on June 3rd when he was caught using a corked bat in an interleague game against the Tampa Bay Devil Rays.

In his first at bat of the game, Sosa hit a broken bat, ground ball to second base that, at first, appeared to plate the Cubs' first run of the game.

However, it quickly became evident that something was wrong as the umpires huddled up around the handle half of the broken bat.

Sosa was ejected from the game, the run was wiped off of the board, and questions immediately arose as to how many of Sosa's then 505 career home runs were cork-aided.

In his defense, Sosa claimed he used the corked bat for batting practice so he could put on a show for the fans and had grabbed it by accident on his way to the plate.

After testing a number of his other bats, including five that had been on display at the Hall of Fame, no other corked bats were found and Sosa served a seven game suspension before returning to the lineup.

Regardless of whether or not it was intentional, this was an embarrassing moment both for Sosa and for the Cubs, and certainly raised some eyebrows around the league.

No. 8: Ron Santo Is Still Not A Hall of Famer

Year: 1985-1998, 2003, 2005, 2007, 2009

While technically not a "moment", there have now been 19 occasions that Santo has been involved in a Hall of Fame vote, be it by standard ballot or veteran's committee. He has been passed up each time.

Rather than give my opinion, I will simply let the statistics do the talking. Below are Santo's career numbers, as well as where he ranks compared to the ten current Hall of Famer's who were inducted as third basemen.

BA: .277 (eighth)
OBP: .362 (seventh)
SLG: .464 (fourth)
H: 2254 (sixth)
HR: 342 (third)
RBI: 1331 (fifth)
R: 1138 (seventh)
9x All-Star
5x Gold Glove

It is certainly hard to say, at least based on the above numbers, that Santo is not one of the top third basemen in the history of the game, and Cubs fans are understandably angry each time he is passed up.

No. 7: Kerry Wood and Mark Prior...Enough Said

Year: 2004

When Kerry Wood struck out 20 batters as a rookie and went on to win the Rookie of the Year, the Cubs seemingly had found the ace that they had been lacking since Greg Maddux bolted in free agency back in 1993.

Even with the Tommy John Surgery he had in 1999, Wood was still a 24-year old flame thrower with worlds of potential when the Cubs took USC pitching prodigy Mark Prior with the second overall pick in the 2001 Draft.

After 2002 saw Prior make an impressive 19 start-audition and Wood prove his health by starting a career-high 33 games, 2003 would be the first of what Cubs fans hoped would be many seasons that the two spent together atop the rotation.

They didn't disappoint.

Prior, posted a line of 18-6, 2.43 ERA, 245 Ks as he finished third in Cy Young voting and ninth in MVP voting. Wood, not to be out done, went 14-11, with a 3.20 ERA, 266 Ks as he led the NL in strikeouts.

While the team was ousted from the playoffs in brutal fashion, hopes had never been higher on the North Side than they were entering the 2004 season.

However, injury struck and the pair combined for just 43 starts and a 14-13 record in 2004 and the Cubs missed the playoffs.

There would be many more injuries to come, as Wood was forced to the bullpen midway through the 2005 season and Prior would again miss starts due to injury, although he did manage an 11-7 record and a league leading 10.2 K/9.

The 2006 season would be the last straw, as the pair combined for just 13 starts and a miserable 2-8 record.

Clearly unable to rely on the health of their two "aces," the Cubs were forced to go a different direction for the 2007 season, signing starters Jason Marquis and Ted Lilly and moving closer Ryan Dempster back to the rotation.

Wood managed to comeback as a closer, making an All-Star team before leaving for Cleveland. Prior on the other hand has had countless surgeries and has not seen big league action since 2006.

Potential is a dangerous word in sports, and these two had all the potential in the world. They will go down as two of the biggest "what ifs" in baseball history.

No. 6: Greg Maddux Signs With The Braves

Date: December 9th, 1992

When Maddux hit free agency following the 1992 season, there was not a more coveted player in all of baseball than the then 26-year old right-hander.

In just six full seasons in the Cubs rotation, Maddux had compiled a 95-75 record with a stellar 3.35 ERA, and had quickly become one of the league's best pitchers.

He was also coming off of his best season to date, as he posted a 20-11, 2.18 ERA, 199 Ks line that won him the Cy Young despite pitching for a 78-84 Cubs team.

After being strongly pursued by the Yankees, and eventually being offered a five year, $34 million contract, Maddux instead signed with the Braves for five years, $28 million and the chance to win a World Series.

This made him the second highest paid pitcher behind David Cone who had just signed a three year, $18 million deal.

The Cubs signed free-agent Jose Guzman to fill Maddux's spot at the front of the rotation, and he went 12-10 in his first and only season in Chicago.

Maddux went 20-10 and went on to win 194 games in 11 seasons in Atlanta, capturing three Cy Young's in the process. Ouch.

No. 5: The Lou Brock Trade

Date: June 15th, 1964

In desperate need of some starting pitching, the Cubs dealt promising young right fielder Lou Brock to the Cardinals along with RP Jack Spring and RP Paul Toth for SP Ernie Broglio, RP Bobby Shantz, and OF Doug Clemens.

The meat of the deal was Brock for Broglio, with Shantz having some name recognition as the 1952 AL MVP, but little else at 38 years old.

Broglio was coming off of an 18-8 season, and at 28 was just entering his prime. In five seasons in the league, he had a 67-50 record, including a 21-9 season in 1960.

Brock, just 25 at the time, had flashed good speed with 40 steals in his two seasons as a starter, but held a .260 career average and didn't get on base enough to leadoff.

This one was seemingly advantage Cubs...seemingly.

Broglio went 4-7 in 16 post-trade starts, and combined to go 3-12 with a 6.61 ERA over the next two seasons. He was out of the league all together by 1967 at just 30 years of age.

Brock, on the other hand, went off after the trade, hitting .348 BA, 12 HR, 44 RBI with 33 SB in 103 post-trade games.

He finished 10th in MVP voting that season, and 15 seasons later he retired, still a member of the Cardinals, but also a member of the 3,000 hit club, the career SB leader, and an eventual Hall of Famer.

This trade goes down as one of the most lopsided in professional sports history, and it is only made worse by the fact that Brock was traded to the Cubs bitter rivals.

No. 4: Leon Durham's Error

Date: October 7th, 1984

First the positives; the 1984 Cubs snapped a 39 year postseason drought, and it all started in Spring Training with some shrewd decision-making by GM Dallas Green.

When the team went on a 13-game losing streak during spring training, Green decided something needed to be done if the Cubs were to avoid repeating their 71-91 record from the previous season.

Before camp was over, he had traded for a pair of new starting outfielders in Bob Dernier and Gary Mathews. That moved Bill Buckner to the bench and he was eventually traded for Dennis Eckersley who would be the team's number two starter.

The big move, however, came at mid season, when the Cubs dealt top prospect Joe Carter and outfielder Mel Hall to the Indians for starter Rick Sutcliffe.

Sutliffe proceeded to go 16-1 in 20 starts after the trade, as he took home the NL Cy Young and gave the Cubs the ace they needed to make the postseason.

The Cubs faced the San Diego Padres in the playoffs, and opened the series with a bang, crushing them 13-0 in Game 1, and then taking Game 2 as they seemed poised to advance to the World Series.

The Padres battled back, however, taking Game 3 and then forcing a Game 5 after Steve Garvey hit a walk-off, two-run home run in Game 4.

The Cubs took an early 3-0 lead in Game 5, but the Padres battled back and tied things at 3-3 with one out and two on in the seventh.

They then sent pinch-hitter Tim Flannery to the plate, and he responded with a sharp grounder to first base that went right between Leon Durham's legs.

A single, a double, and another single later and the Cubs were down 6-3 with the momentum squarely on the Padres side.

And just like that the Padres stud closer Rich Gossage slammed the door with a two inning save, and the Cubs were eliminated.

No. 3: The 1969 Collapse

Date: September 2nd through the end of the season

The 1969 Cubs are a team that will forever be mentioned among pro sports' most epic collapses. The team spent a grand total of 155 days in first place and seemed destined to make a playoff run.

That season, the team fielded what may have been their most impressive roster, at least on paper, since their early 1900s teams.

With the likes of Ernie Banks, Billy Williams, Fergie Jenkins, Ron Santo, Don Kessinger, Randy Hundley, and Glenn Beckert, simply put, they were really, really good.

After Ken Holtzman threw a no-hitter on August 19th, the team took their biggest division lead of the season, up 8.5 games on the Cardinals and 9.5 on the Mets.

With all the momentum in the world on their side, they seemed well on their way to October.

They then proceeded to lose 17 of their last 25 games to complete one of the largest collapses in baseball history, as they finished a full eight games behind the "Miracle Mets," who won 38 of their last 49 games.

Many things have been blamed for the plunge: the fact that manager Leo Durocher ran the same lineup out day in and day out during the slide, the gaping hole in center field, the incredible lack of depth, even a certain feline pictured above.

In the end, it was a combination of a lot of things, but mostly just some terrible luck that makes the 1969 Cubs the most talked about second place team in baseball history.

No. 2: The Bartman Incident

Date: October 14th, 2003

I can't even look at that picture, without my stomach turning.

The Cubs had a World Series trip in their grasp.

With a three run lead, and arguably the best pitcher in baseball over the last two months of the season in Mark Prior on the mound, the Cubs found themselves just five outs from their first World Series trip in 58 years.

Prior was tossing a gem, working on a three-hit shutout with Juan Pierre on second and one out in the top of the eighth inning. With Luis Castillo at the plate, the slap hitting lefty lofted a foul ball behind the Cubs bullpen down the left field line.

As Cubs left fielder Moises Alou approached the stands and attempted to make a leaping catch, a fan in the front row reached out for the ball, deflecting it and preventing what would have been the second out of the inning.

As Alou stood shouting into the stands, and the Cubs made a desperate appeal for fan interference, it quickly became evident that the team had lost their composure.

Castillo went on to draw a walk, which Ivan Rodriguez followed with an RBI single to break up Prior's shutout and put the tying run on base.

With the red hot Miguel Cabrera at the plate, Prior managed to induce an easy ground ball to shortstop Alex Gonzalez for what looked to be an inning ending double play.

Instead, the usually sure handed Gonzalez booted it, all runners were safe, and the bases were now loaded.

That was followed promptly by a Derrek Lee double that chased Prior from the game and tied things up at 3-3. From there the Marlins piled it on, scoring eight runs in the inning and forcing a Game 7.

After leading 5-3, and with ace Kerry Wood on the mound, the Marlins again came back and beat the Cubs 9-6, as they won the pennant and moved on to face the Yankees in the World Series, eventually winning the series in six games.

No. 1: The Curse of the Billy Goat

Date: October 6th, 1945

For those who do not know the story, here's how it goes:

In 1934, a man by the name of William Sianis purchased what was then Lincoln Tavern in downtown Chicago. One day, shortly after the purchase of the bar, a billy goat that had fallen off of a passing truck wound up in his bar, and the bar owner became known as "Billy Goat" Sianis because of it.

Sianis embraced the nickname, changed the name of the bar to the Billy Goat Tavern, and soon both the tavern and tavern owner became rather well know for their connection to billy goats.

Then, in 1945, Sianis purchased two tickets to Game Four of the 1945 World Series between the Cubs and the Detroit Tigers, with the Cubs leading the series 2-1. With the second ticket, Sianis brought his pet billy goat Murphy along with, in hopes of bringing the North Siders some luck.

However, upon reaching the stadium, the goat was not allowed inside by the ushers. When Sianis appealed to Cubs owner P.K. Wrigley, he was told that he could enter but the goat could not, "because the goat stinks," as Wrigley put it.

Angered, Sianis threw up his arms and shouted, "the Cubs ain't gonna win no more." The Cubs went on to lose game four, as well as the next two games as the Tigers took the series.

The Cubs have not seen the World Series since that season, and the fabled "Billy Goat's Curse" has reared its ugly head time and again.

Believe in the curse or not, it is a huge part of Cubs history and to this point has not been proven wrong.