1908 CUBS
Key players
The returning World Series champs were stacked with talent—and awesome nicknames—including 29-game winner “Three Finger” Brown and 130-pound second baseman Johnny “the Crab” Evers.
Team controversy
The pre–Billy Goat Curse Cubbies were beneficiaries of “Merkle’s boner”, a legendary baserunning gaffe by Fred “Bonehead” Merkle of the New York Giants that nullified a Giants win. The two teams ended up tied for first, with the Cubs taking the make-up game to win the National League.
Fan fashion
Men wore shirts, ties, dark wool trousers and jackets, and straw “boater” hats; ladies donned dark stockings, petticoats and long skirts that left much to the imagination.
Series tickets
Regular-season tickets cost a quarter to 50 cents, but owners quadrupled the prices for the World Series—just like today.
Beer price
A bottle of beer cost a dime, but many fans filled their own bucket with booze for a nickel at area taverns before the game.
Postgame hangout
Tipplers (including many Cubs players) downed Old Styles at Biggio Brothers Saloon, across the street from the Cubs’ former home, the West Side Grounds, located at Polk Street and present-day Wolcott Avenue (then named Lincoln Street).
2008 CUBS
Key players
Pitching ace Carlos Zambrano had a strong season (including throwing the Cubs’ first no-hitter in 36 years) and third baseman Aramis Ramirez smacked in more than 100 RBI.
Team controversy
Manager Lou Piniella’s steady hand has kept the dugout controversy-free this season. But things weren’t so smooth in April when fan complaints led the Cubs to try to stop sketchy vendors from peddling racist Kosuke Fukudome T-shirts featuring a slanty-eyed cartoon bear.
Fan fashion
Inspirational IT’S GONNA HAPPEN T-shirts and wristbands; women prefer bikini or halter tops in the bleachers
Series tickets
If the Cubs make it to the Fall Classic, infield club box seats will cost $250—but you’ll need to sell a kidney to afford the astronomically higher scalper prices.
Beer price
$6.25 for a 16-oz Old Style
Postgame hangout
So many people flock to Murphy’s Bleachers (3653 N Sheffield Ave) before and after games, a bridge should be built to connect it with Wrigley.
2005 SOX
Key players
Pitcher Mark Buehrle led a stellar rotation with a 3.12 ERA, while first baseman Paul Konerko crushed 40 dingers. Acquisitions such as outfielder Scott Podsednik (59 stolen bases) and catcher/professional irritant A.J. Pierzynski paid dividends, especially down the stretch.
Team controversy
In Game 2 of the American League Championship Series, Pierzynski sneakily sprinted to first after swinging at an apparent ball in the dirt for strike three. The ump ruled him safe, and the Sox won the game one batter later.
Fan fashion
Konerko jerseys; plus a high percentage of jeans-clad dudes going shirtless to show off their GOOD GUYS WEAR BLACK tattoos
Series tickets
Lower reserved seats went for $140.
Beer price
$5.50 for a 16-oz Miller Lite
Postgame hangout
It’s a sweaty dive filled with framed pictures of Italian guys, but Jimbo’s (3258 S Princeton Ave) was the place to sing “Don’t Stop Believin’” after the Game 4 victory. Find out what two regulars think here.
2008 SOX
Key players
Out-of-nowhere Gavin Floyd led the pitching staff in wins. Outfielder Jermaine Dye, ’05 World Series MVP, had another monster year, and rookie second baseman and Cuban exile Alexei Ramirez put up huge numbers in his first season free from Castro’s clutches.
Team controversy
To help break a May hitting slump, a Sox player had the genius idea of stashing two female blow-up dolls in the dugout surrounded by “strategically placed” bats. Media called it “infantile and sexist,” but skipper Ozzie Guillen refused to apologize.
Fan fashion
Carlos Quentin jerseys; plus those same shirtless dudes, but now the tattoos say 2005 WORLD SERIES CHAMPS
Series tickets
Prices will jump to $175 if the Sox return to World Series form.
Beer price
$6.25 for a 16-oz Miller Lite
Postgame hangout
Threatened with eviction after its lease expired in ’06 (reportedly to make way for the epitome of Wrigleyville cheese, a John Barleycorn), Jimbo’s is still kicking while owner Jimbo Levato fights the power in court.