The Best Recent Cubs Teams to Fall Short

Bartman about to catch hell.

Cheering for the Cubs means having a bruised romantic spirit and a painful attachment to the underdog. When your favorite team has not been the best since Teddy Roosevelt was president, and the only living souls who were there to see their triumph must have been baby vampires, it’s hard to escape silly thoughts of curse-inducing goats.

          

The studs of 1908 have come close to redemption on more than a few occasions. With the current squad bursting with talent, the Cubs are the odds-on favorite to win the World Series. Maybe redemption awaits. 

Or, maybe, just maybe, how about more heartbreaking failure?! That was the case for the following lovable losers in recent memory.

 Where's Maddux?! No wonder they blew it.

1989: The height of the Sandberg/ Dawson/ Maddux era, the ’89 squad was complimented by All-Stars such as 16-game winner Rick Sutcliffe and closer “Wild Thing” Mitch Williams. Confident vets blended with the emergence of Rookie of the Year Jerome Walton and the slick-fielding, on-base machine Mark Grace. The cartoonish legend Harry Carrey narrated their 93-win season with hysterical hope and joy, but the ’89 Cubs lost the decisive game five of the NLCS to the Giants.   

 '98 Sosa was so fun to watch.

1998: Not as deep or balanced as the previous team on the list, these Wild Card winners were more fun than great. They were led by league MVP Sammy Sosa, who blasted 66 homers and drove in 158 runs during one of the most astounding seasons to ever be marred by an asterisk. In an unforgettable performance against the Astros, Kerry Wood struck out 20 hitters to match his age, tying the MLB record en route to ROY honors. But Wood’s late-season stint on the DL coupled with a supporting cast that was good but not premier led to a first-round sweep by the Braves.

Fun fact: Nobody likes the Florida Marlins. 

2003: The Steve Bartman debacle... It was more of a Shakespearian tragedy than a mere sports disappointment. Rotation talent had been added around Wood in the form of young aces Mark Prior and Carlos Zambrano. Sosa became surrounded by speed and on-base skills at the top of the lineup and power in the middle. Dynamic leadoff man Kenny Lofton and budding slugger Aramis Ramirez were fleeced from the Pirates in a mid-season deal to bolster the charge to the division crown. The squad even exacted revenge on the Braves in the Division Series. They were on the cusp of beating the Marlins to reach the World Series when fan interference in foul territory started a horrific meltdown in game six of the NLCS. A forgettable game seven sealed their fate. 

 All-Stars. Not pictured: More All-Stars.

2008: Led by grizzled skipper “Sweet” Lou Piniella, these Cubs amassed 97 wins—the same total as the last team in franchise history to reach the Series in 1945. In a display of their all-around prowess, they fielded eight All-Stars—four position players, two starters, and two relievers. Their All-Star snubs included the always productive Derrek Lee and the embodiment of the team’s depth and range, IF/OF Mark DeRosa. Catcher Geovany Soto earned Rookie of the Year honors, Alfonso Soriano smacked 29 bombs, and Zambrano punctuated a stellar campaign by dealing a no-hitter in September. The team’s fortunes turned for the worse in October when they were swept by the Dodgers in the NLDS. Following a magical six months of baseball, the ’08 Cubs might be best-remembered as a postseason dud.

  Cornerstones. 

2015: If there’s cause for optimism in this list, it’s that the most recent Cubs squad exceeded expectations. They overachieved, due in large part to the guidance of new manager Joe Maddon, a zany guru known for thinking outside the box. Preceded by bad teams that were the result of a savvy rebuilding project, farm system studs emerged ahead of schedule. Namely, Kris Bryant drove in 99 runs and continued the trend of the team fielding a ROY in a playoff season. Other patterns held true as shortstop Addison Russell had been swindled from the Athletics a year earlier. Right-hander Jake Arrieta was basically stolen from the Orioles; he posted a dazzling 1.77 ERA on his way to becoming the Cy Young winner. The team won 97 again, and unlike any of the predecessors cited, they prevailed twice in the playoffs, beating the Pirates in the Wild Card one-and-done and their bitter rivals the Cardinals.

Their run, too, ended before the World Series. But the North-siders are clearly a franchise on the rise, with a window of success that should be open for several years. By adding Ben Zobrist—one of the toughest outs in baseball—as well as flame-throwing closer Aroldis Chapman, they’ve become the fastest team to 80 wins. The excellence of these Cubs contrasted with the power of the drought has drawn comparisons to the unstoppable force and the immovable object.

Cubs fans believe hope is that unstoppable force. In the greatest storyline baseball has told years, we’ll see in October if that hope at long last pays off and leads to the ultimate redemption.