The five best sports moments in Chicago since 1993

The Bears mauled the New England Patriots 46-10 in Super Bowl XX on January 26, 1986, to earn the organization’s lone Vince Lombardi Trophy. Prior to the Bears’ triumph in the mid-1980s, Chicago’s four major sports franchises had suffered a 22-year drought between titles. Fortunately for fans of Windy City athletic squads, the Bulls made championships commonplace throughout the 1990s. Accordingly, let’s rank Chicago’s best sports moments of the past quarter-century.

5. 2005 WHITE SOX

The 2005 White Sox and 1927 Yankees are the only teams in Major League Baseball history to lead their divisions from start to finish, win the most regular season games, and sweep the World Series en route to a crown. Powered by stellar pitching, the White Sox finished 99–63 and went 11-1 in the playoffs to clinch their first championship in 88 years. Although exceptional throughout the 2005 campaign, Mark Buehrle, Jon Garland, Freddy Garcia and Jose Contreras especially overwhelmed the Los Angeles Angels of Anaheim’s hitters in the ALCS. During that lopsided series, all four Sox starters tossed a complete game and the quartet logged a total of 44.3 out of 45 innings. After trouncing the Angels in five games, the Sox swept the overmatched Houston Astros.

4. 1995-1996 BULLS

Michael Jordan and the Bulls conquered the Phoenix Suns in six games to secure a three-peat in June 1993. Roughly four months after earning his third consecutive NBA Finals Most Valuable Player Award, a 30-year-old Jordan retired on October 6. The Bulls remained a formidable squad while His Airness competed on the diamond for the Birmingham Barons. However, Phil Jackson’s unit was unable to collect another Larry O’Brien NBA Championship Trophy without Jordan. Jordan returned to the Bulls for a full season in November 1995 and was obsessed with regaining his unrivaled status on the hardwood. The Bulls proceeded to go 72-10 and outclass the Seattle SuperSonics in the 1996 NBA Finals to win their fourth crown in six seasons.

3. 2009-2010 BLACKHAWKS

PHILADELPHIA – JUNE 09: The Chicago Blackhawks pose for a team photo after defeating the Philadelphia Flyers 4-3 in overtime and win the Stanley Cup in Game Six of the 2010 NHL Stanley Cup Final at the Wachovia Center on June 9, 2010 in Philadelphia, Pennsylvania. (Photo by Jim McIsaac/Getty Images)

The Blackhawks axed the competition throughout the 2009-2010 campaign and ultimately trumped the Philadelphia Flyers 4–2 to capture their first Stanley Cup championship since 1961. Center Jonathan Toews was named the Conn Smythe Trophy winner for his feats during the playoffs. This version of the Blackhawks, led by a 22-year-old Toews and a 21-year-old Patrick Kane, are frequently lauded as one of preeminent squads in NHL history.

2. 1997-1998 BULLS

The Bulls overcame the Utah Jazz in six grueling games to complete their second three-peat of the 1990s. Trailing by a point, Jordan nailed a 20-foot jumper with 5.2 seconds remaining to give the Bulls a definitive 87-86 lead. Jordan was awarded his sixth NBA Finals Most Valuable Player Award for his spectacular outings against the Jazz. Jordan retired in January 1999 and the Bulls have failed to advance to another finals since His Airness flew away from the Windy City.

1. 2016 CUBS

The Cubs thrived throughout the 2016 regular season and outlasted the Cleveland Indians to achieve their first World Series title since 1908. Illinoisan Ben Zobrist won World Series Most Valuable Player honors for his prolific efforts. While the Bulls, Blackhawks and Bears are beloved, the Windy City is a baseball town and the North Siders are its glamorous franchise. Hence, the 2016 Cubs are arguably the most iconic team in the annals of Chicago sports.