Chicago Cubs: The 5 Worst Moments in the Team's Tortured History

Reed Domer-Shank@ReedDS20Correspondent IMarch 30, 2011

Chicago Cubs: The 5 Worst Moments in the Team's Tortured History

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    As a Reds supporter, I love talking to Cubs fans.

    See, in Cincinnati, we’re used to losing. We’re familiar with the bruised, aching feeling that follows every season gone bad. We know all too well the dejection of finishing fifth or sixth in the division, with no realistic prospects of hope on the horizon.

    Yet, no matter how low a team like the Reds sinks into the vacant, hollow abyss of obscurity, it helps to know that there are Cubs fans out there whose plight makes ours seem like a paddleboat ride down a chocolate river. I know a few guys like this. So, luckily for me, whenever I’m in need of some grounding, ready to fire my fan-hood right into the toilet bowl, I know who to call.

    These guys have spent their life in the pisser, and can tell you exactly how it tastes.

    Now, there are certain areas in the sporting world where we dare not tread lightly, without deference to their importance or reverence to what they have meant.

    The ineptitude of the Cubs is one of them.

    Therefore, when asked to create a list of the worst moments in Chicago Cubs history, rather than compile a stale list of dates and names, I decided to reach out to genuine Chicago faithfuls for some meaningful commentary. Guys who, either through our family, school, or work relationships, have exhibited precisely the level of bile I expect out of Cubs fans. Sick to their stomachs, jaded to their core.

    I reached out to all the Cubs fans I knew and, though responses varied, I wasn’t surprised to get the most scintillating stuff from my "uncle" Pete. A family friend, lifelong Chicago resident and business owner, and Cub-cynic extraordinaire, Pete used a series of e-mails to illustrate the steaming pile of dung that has come to define Cubs fandom. With vigor, he was happy to enlighten me on the lowlights of his proud, tortured tenure.

    What follows are the worst in a long succession of sordid Cub moments, with agonized commentary from the biggest Cubs fan I know. 

5. Prior and Wood

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    It’s widely accepted amongst baseball fanatics that the most valuable commodity in the game is a legit, bona fide ace. True aces combine dominating “stuff” with the endurance to go deep into games, limiting teams to one or two runs over seven innings or more.

    Every team hopes to somehow stabilize one at the top of their rotation, and build a staff around them.

    Well, in the early part of this century, the Cubs had TWO. Or so they thought.

    In 2001 the Cubs drafted Mark Prior, a hard-throwing right-hander with the No. 2 overall pick in the draft, hoping to soon pair him with their other thoroughbred hurler, Kerry Wood.

    At the time, Wood was still the hope of the Chicago franchise, having shown incredible promise in his first few injury-spotted years in the league (including a 20-strikeout, one-hit shutout in his fifth career start.) So, with Prior in the fold, it seemed the Cubs would soon have the firepower in their arsenal to sniff their first World Series in nearly 100 years.

    All went according to plan – briefly.

    Prior reached the Majors the very next season, and in his first full year with the club (2003) he combined with Wood for 32 wins, leading the club to their first NLCS in 14 years, and only their fourth playoff appearance in the last 59.

    Due in large part to the simultaneous emergence of Prior and Wood, 2004 looked to be the year the Cubs’ historic misfortune would finally be reversed. Yet, accustomed to defeat, North-siders shouldn’t have been surprised when things went south in a hurry.

    The 2004 season saw the commencement of a devastating spate of injuries for both pitchers. Wood, seemingly fully-healed from his 1999 Tommy John surgery, lost nearly two months that season for a strained triceps and never truly returned to form.

    Likewise, Prior lost two months with a sore Achilles tendon. Then, after neglecting to undergo Tommy John, the once-heralded prospect saw a more rapid decline than Wood, sustaining injuries to his elbow, shoulder, and oblique, and managing just two more fragile seasons in the league.

    In the years since that fateful 2004 campaign, Cubs fans have been left to lament what might have been with their two aces. Questions remain on the Cubs’ management (or mismanagement) of the two studs, and then-manager Dusty Baker, now with the Reds, still is saddled with the onus.

    Fans are lucky if a promising tandem like Wood/Prior comes along once in a generation, so to see their talent shine so briefly before being snuffed out was a blow, even to a fan-base so hardened by defeat.

    Uncle Pete’s take:

    Even today I can barely believe how badly we effed this one up. I swear, if Jesus taught the Cubs to turn water into wine, they’d end up losing the recipe and trying to bottle p*ss. Pretend you spent 40 years married to (bleeping) Judi Dench. Then, pretend that for about four days you were married to Julia Roberts and Demi Moore at the same time, and all they ever wore were Hooters outfits. That’s how I felt in 2003. Then, starting in ’04 it was like Demi and Julia both got hit by a bus and I’ve been dating Judi Dench again ever since. On one hand, I’m used to it...but that doesn’t make it any less disgusting.”

4. Leon Durham

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    In 1984, the Cubs made the playoffs for the first time since ‘45. Their ace, Rick Sutcliffe, won the Cy Young. Their second baseman, Ryne Sandberg, won NL MVP and was considered the best in the game at his position. Their manager, Jim Frey, was named Manager of the Year.

    Things couldn’t get more bonkers.

    Then, after going up 2-0 in their first series in 40 years, the Cubs did what the Cubs do best.

    They began to fail miserably.

    On the strength of a Steve Garvey Game 4 home run, the Cubs relinquished two games to the Padres, allowing the series to even at 2-2. Then, after jumping out to a 3-0 in the decisive Game 5, the Padres clawed back to tie it 3-3 in the seventh inning.

    With one out and a man on second, Cubs first baseman Leon Durham (a converted outfielder) let a routine ground ball trickle through his legs, an error that led to a 6-3 Padres win. A mere three innings away from a trip to the World Series in ‘84, the Cubbies have won one playoff series since.

    Chicago fans view the Durham error as one of several benchmarks in a consistent pattern of epic Cubs failures.

    Uncle Pete’s take:

    “I don’t know about anyone else, but I’d love to smack Leon Durham in the face with a (bleeping) board, ‘cuz that’s what he did to me and my buddies in ’84. I was 24 at the time, and I was SURE we were going to win it all. I can’t even remember who we would have played in the WS, but it didn’t matter. It was destiny. As it turned out, Durham pulled one of the biggest boners in Cub history, we lost the series, and Cubs fans spent the next 100 years getting chased from the playoffs like a chubby postal worker. OK, maybe it hasn’t been 100 years. But it’s damn sure feels like it.”

3. Brock for Broglio

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    June 14th, 1964. One of the worst days in Cubs history? Absolutely.

    At the time, Lou Brock wasn’t a household name. In two full seasons, he’d proven himself to be a base stealer whose main problem was not being able to get on base (his OBP to that point hovered around .300). Cubs brass identified this as a red flag – and understandably so.

    So, in need of pitching, Chicago shipped Brock to division-rival St. Louis in a deal that brought Ernie Broglio, an 18-game winner from the year before.

    To be fair, the Cubs seemed to be putting their best foot forward with this one. No one could have predicted the carnage that would ensue.

    Broglio’s brief, abysmal stint in Chi-town would have been more than enough to make the trade reek. The headliner of that 1964 deal spent just two and a half seasons as a Cub, posting a 6.61 ERA and accumulating just 3 wins in ’65 and ’66 combined.

    On the other hand, Brock’s post-trade play in 1964 ALONE would have been the cherry on top of what became a Chicago crap-sundae. The right-fielder hit .348 the rest of the way for the Cardinals, providing a glimpse of just how dismal the deal would end for the Cubs, in retrospect.

    Ultimately, Brock spent 15 years in St. Louis, wracking up over 3,000 hits, nearly 900 stolen bases, and eventually celebrating with a plaque in Cooperstown.

    Uncle Pete’s take:

    “Even I am too young to really feel the burn of this one, but my Pops never forgot. Ten years after the deal was made, Brock swiped 118 bases – more than anybody else in the league. I can still remember hot nights in Chicago where we’d lose to the Cards. Dad would get up silently from his old chair, shuffle into another room, and I would hear him mumble ‘Lou (bleeping) Brock.’ Today, Lou Brock is probably one of the greatest players that ever was. Ernie Broglio??? Who the (bleep) knows.”

2. Steve Bartman

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    This might be one of the most poignant pictures in the modern era of baseball.

    Not since the Durham error in 1984 had the Cubs even gotten CLOSE to a World Series. In 1998, a Sammy Sosa-led Cubbie squad made it to the NLDS, only to be emabarassed 3-0 by the Atlanta Braves. Yet, in 2003, led by the transcendent performances of Prior and Wood, Chicago advanced past those same Braves to meet the Marlins in the NLCS.

    Up 3-2 in the series, the Cubs found themselves leading 3-0 heading into the eighth inning; six outs away from a shot at their first Championship in, oh, an eternity.

    What transpired from that point forward has been well-documented, and promises to fester in the Chicago consciousness forever.

    With one out in the inning and staff ace Prior in the middle of potentially the greatest performance of his career (a three-hit shutout), Marlins second baseman Luis Castillo sent a foul ball careening toward the left field stands. Cubs’ outfielder Moises Alou approached and attempted a leaping grab, only to watch as little Steve Bartman reached into the fray, knocking the ball away, and stamping his indelible fingerprints on the annals of baseball history.

    The aftermath was gruesome. Alou raged. Prior stood in shock. And Bartman was led away by security amidst a throng of boo’s.

    With Prior shaken, the Cubs went on to lose the game and eventually the series, cementing Bartman’s place as Chicago’s Voldemort squared. Though the Cubs have taken the lion’s share of baseball’s whippings over the years, the wounds from the 2003 disaster are fresh.

    In 2004, the Bartman Ball was publicly detonated. The wreckage of the 2003 collapse remains today.

    Uncle Pete’s take:

    “To be honest, I actually feel bad for Bartman. I mean, if you look at the situation from an outsider’s perspective, that play probably didn’t even matter. Prior is the one that got bombed that inning. The Cubs were the ones that could only score three damn runs. But Bartman – poor, nerdy Steve Bartman – was the one with booze tossed on him and cops protecting his house. I’ll admit though… at the time? I would have rooted against Bartman if he were fighting Osama Bin Laden. I’d have fed his kids to Mike Tyson. Most Chicagoans still would.”

1. Billy Sianis and the Curse of the Billy Goat

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    The Curse of the Billy Goat. Any true Cubs fan may as well stop reading now.

    No Chicago kid grows up without having this legend ingrained in the very fiber of their being. Children are rocked to sleep at night with the tale being whispered in their ear, a gentle warning of the pain that lies ahead.

    As legend has it, the misery of Cubs Nation traces back to 1945, when all one man wanted to do was see a game…accompanied by his goat.

    Indeed, William “Billy Goat” Sianis, owner of the Billy Goat Tavern and lifelong friend of a real, live billy goat (you can’t make this stuff up) showed up to watch Game 4 of the 1945 World Series between the Cubs and Tigers, with two tickets in hand.

    One, of course, was for Billy. The second, he insisted, was for his goat.

    As would likely be the case at any stadium, restaurant, brothel, crackhouse, etc. (really anywhere BESIDES a barn), Sianis’ smelly friend was refused service. In frustration, Sianis allegedly proclaimed that THAT would be the end of the Cubs winning.

    And by George, he was right.

    In the 65 seasons since Sianis’ hex, the Cubbies haven’t been back to the World Series. With every season that passes, the Cubs find new ways to be Durhamed, Broglioed, and Bartmaned out of wins.

    Faces may change in Chicago, and win totals may vary, but it seems until someone lets a goat inside Wrigley’s gates, the phrase “Wait ‘til next year” will endure.

    Somewhere, Billy Sianis smiles.

    Uncle Pete’s take:

    “In my lifetime, the Cubs have traded away Hall of Famers, dangled their own stars to their biggest rivals, stumbled their way through the most pivotal of moments, flushed their prospects’ talents down the crapper, catered to obvious steroid-users and clubhouse-cancers, signed guys like Alfonso Soriano and Milton (bleeping) Bradley, and managed to collapse in every way, shape, and form. As Cubs fans, we grow up hoping we’ll win, and knowing we’ll lose. We go to the field expecting the worst, even though every piece of us longs for the best. As Cubs fans, we keep what little optimism we have hidden. We learn early on what it means to be a Loveable Loser…and we hate every damn minute of it.(Bleep) that (bleeping) goat.”