Sid Ranks Em’ All: Top 5 Toughest Losses in Chicago Sports

Doug Pensinger/Getty Images Sam Shields of the Green Bay Packers intercepts a pass intended for Johnny Knox of the Chicago Bears late in the second quarter in the NFC Championship Game, one of Sidney Brown's toughest losses ever in Chicago sports.

Doug Pensinger/Getty Images
Sam Shields of the Green Bay Packers intercepts a pass intended for Johnny Knox of the Chicago Bears late in the second quarter in the NFC Championship Game, one of Sidney Brown’s toughest losses ever in Chicago sports.

Sidney Brown is known as the go-to guy for hockey info on Regal Radio, but what you may not know is that he has quite the encyclopedic brain for all sports. In “Sid Ranks Em’ All” you’ll get to read his unique take on the best and worst of sports with specific lists spanning all playing fields.

In the city of Chicago, we can all agree that we love our sports teams, ride or die.

From the Bears to the Blackhawks, the Cubs to the White Sox and, of course, the Bulls. No matter what number of teams you cheer for, there’s been some history for a fan to be proud of, but we also all know that rooting for Chicago teams naturally brings about moments that aren’t very kind for the most part.

Take, for instance, the failed attempt for the Hawks to repeat as Stanley Cup champions this past spring. Listening to sports radio locally the next day you were bombarded with a number of fans overreacting, saying that the Hawks’ season was a disappointment after losing in Game 7 at home to the eventual Stanley Cup champion Los Angeles Kings and comparing it to the 2003 Chicago Cubs’ loss to the eventual World Series Champion Florida Marlins in the National League Championship Series. It drove this writer crazy, but it got me to thinking about the toughest losses I’ve seen in my 33 years on earth watching Chicago Sports.

Some people may still recoil from the memories of these moments while others just soberly use them as history lessons. No matter how you deal with these losses, its easy to draw from them as important times where our respective emotional connection to our teams and sports in general either brings out the best or the worst in us.

Here are my top 5 toughest losses in Chicago sports history:

5) Toronto Blue Jays @ Chicago White Sox — American League Championship Series, Game 6 (October 12, 1993)

The 1993 White Sox were a young team on the rise that caught fire in the middle of the summer, winning the American League West with a 94-68 record. Frank Thomas won the regular season MVP while ace pitcher Jack McDowell won the Cy Young Award but before the postseason awards were given out the Sox attempted to reach the World Series for the first time since 1959 and the team that stood in their way were the defending World Series champion Toronto Blue Jays.

This was clearly the best White Sox squad that my young eyes had seen. Along with Thomas and McDowell, the team was packed with talent at just about every position — Tim Raines, Lance Johnson, Ozzie Guillen, Robin Ventura, there was the feel-good story of the returning Bo Jackson as well as one of the best young pitching rotations in the game, featuring Wilson Alverez, Jason Bere and Alex Fernandez. This club looked like it had the talent to go all the way.

After losing the first two games at home, the Sox rebounded by winning 2 of 3 games north of the border, putting them in a 3-2 hole for this first tragic Chicago sports moment. With two more home games in front of them, the South Siders had a chance to knock out the veteran Blue Jays, but it was not to be.

The 1993 ALCS wound up proving that the Blue Jays were a better ball club, one of the best of that era clearly. It was sickening, though, to see the Blue Jays players celebrating on Comiskey Park turf after their 6-3 clinching victory, I couldn’t do anything else but hang my head realizing that my favorite baseball team was still at least a year away from competing in a World Series, that year would turn into 12 before the Sox finally brought a World Series title back to Chicago. Meanwhile, after eliminating the Sox, the Blue Jays knocked off the Philadelphia Phillies in grand fashion to win their second straight title, becoming the first team since the ’78 Yankees to repeat as champs.

4) Chicago Blackhawks @ Vancouver Canucks — Stanley Cup First Round, Game 7 (April 26, 2011)

Rich Lam/Getty Images Troy Brouwer (L) consoles goalie Corey Crawford after the Blackhawks' 2-1 loss in overtime to the Vancouver Canucks in Game Seven of the Western Conference Quarterfinals during the 2011 NHL Stanley Cup Playoffs.

Rich Lam/Getty Images
Troy Brouwer (left) consoles goalie Corey Crawford after the Blackhawks’ 2-1 loss in overtime to the Vancouver Canucks in Game Seven of the Western Conference Quarterfinals during the 2011 NHL Stanley Cup Playoffs.

In the season leading up to this tough loss, the Hawks were coming off their first Stanley Cup Championship in 49 years in 2010 and were looking to repeat as champs.

After depleting their roster due to salary constraints, the Hawks struggled to make the playoffs and only managed to clinch on the last day of the regular season thanks to the Minnesota Wild defeating the Dallas Stars, giving Chicago the eighth spot in the Western Conference, awaiting them was the top-seeded Canucks, who were anticipating their third straight playoff battle with the Hawks.

Vancouver proceeded to dominate the defending champs through the first three games of the series, winning them all but facing elimination the Men in Red responded like champions and forced a seventh game in Vancouver.

The Canucks controlled most of Game 7 but the Hawks found energy courtesy of captain Jonathan Toews tying the game late in regulation. As a fan, I thought that we were bound to make history with the Hawks pulling off a rare series victory after trailing 0-3, but it wasn’t in the cards. Vancouver wound up slaying the dragon in overtime courtesy of Alexandre Burrows’ game-winner, with a 2-1 victory the result of the Hawks falling short.

Was the 2010-11 Hawks team the best team on paper? Not at all, but they gave fans a ride to remember and by the end retained some hope that they could have made history against an emerging hated rival.

Like the Sox, the Hawks were a pit stop for a team on its way to its sport’s final series, but Vancouver lost its championship shot to the Boston Bruins in seven games. Bookending things, the Hawks knocked off those same Bruins in 2013 for another Cup win.

3) Green Bay Packers @ Chicago Bears — 2010 NFC Championship Game (January 23, 2011)

The 2010 Chicago Bears were looking like a team of destiny, possibly a championship squad to pair with the Hawks, who won earlier that year, but they only wound up showing the later disappointed hockey team how to really close a season out on a downer.

After winning the NFC North Division title while eternal rival Green Bay struggled through most of the season (only to clinch the final playoff spot on the last game of the regular season, defeating the Bears in Lambeau Field). The Packers went on to win two road games at Philadelphia and Atlanta as a Wild Card team, setting up an unprecedented playoff matchup with the Bears, who dispatched the upstart Seattle Seahawks the week before after a bye week. The Super Bowl was now on the line between the oldest rivals in football.

The Packers started off strong in a raucous Soldier Field setting, while the Bears had trouble with their offense. Bears quarterback Jay Cutler went 6-14 passing for 80 yards and eventually left the game with a knee injury, causing major controversy throughout the game and a reputation he still has trouble shaking off.

With the Packers leading 14-7 in the fourth quarter, the Bears plugged in third string QB Caleb Hanie and in his most famous performance Hanie went 13-of-30 passing for 153 yards with a touchdown pass and an interception, but it was that pick to Packers defensive lineman B.J. Raji that sealed the deal for the Cheeseheads, who were now up 21-7. The Bears shortened the gap to 21-14 late but didn’t have enough to produce a complete comeback, the damage was done.

Watching the Packers players and their fans celebrate on the Soldier Field turf made me as angry as anything I’ve seen, the feeling was so lasting it made me so upset that I refused to watch the following Super Bowl where the Packers would eventually beat out Pittsburgh Steelers.

Always the way the 2011 playoffs ended will stay with me and bother me — what if Jay Cutler would have stayed healthy, could he have rose to the occasion? What more could the Bears top rated defense have done, maybe they would have carried the team the rest of the way?

Would the Bears have won the 2010 Super Bowl? I guess we’ll never know and after watching the NFL Network program “America’s Game” on the Packers just one time I’ve formed a natural reaction to watching highlights from that NFC title game that is hard to deal with.

2) Chicago Bulls @ Detroit Pistons — Eastern Conference Finals, Game 7 (June 3, 1990)

It was the third straight time these two were meeting in the playoffs, and the second time in the Eastern Conference Finals — the Bulls and the Pistons were in the midst of playing out one of the NBA’s great rivalries.

The Pistons were coming off their first NBA championship win in 1989 while the Bulls were climbing up the ladder as the team on the rise led by the league’s most electrifying player, Michael Jordan. Known as the Bad Boys for their physical play, the Pistons used a strategy of defensive toughness and quick scoring to mentally deflate opponents and the Bulls famously became the team that fell hardest to that style of play.

After losing in six games in the ECF in ’89, the Bulls were focused this go around, thanks to the promotion of Phil Jackson as head coach the off-season before and with Jackson in charge came a new reliance on assistant Tex Winter’s pioneering triangle offense. Chicago had more tricks up its sleeve this time around.

Both teams held court in each of their three home games to start the series, bringing things to the decisive seventh game at the Palace of Auburn Hills where the Bulls at that time had a history of trouble, previously winning just one postseason game there (Game 1 of the ’89 ECF).

The Bulls had hope but the Pistons had the experience and the home court advantage on their side and they once again intimidated the Bulls and sending them home packing after a 93-74 victory. Scottie Pippen’s pre-game migrane headache became a representative storyline for the frustration the Bulls had in trying to get past the Pistons and his 2-point performance said everything else. Jordan expectedly led the Bulls with 31 points but support was lacking.

As a nine-year-old, I remember coming to grips with that sickening feeling that the Pistons had beat the Bulls AGAIN and wondering will the nightmare ever end? Watching the CBS broadcast it also stuck out how a Pistons fan held up a sign saying “Maybe Next Year Michael,” while another fan held a red Bulls Jordan jersey and punched it several times. After seeing that, I wanted to punch the whole Pistons team and their fans in their faces.

The Pistons went on to clinch their back-to-back titles after defeating the Portland Trail Blazers in the Finals. Revenge finally came the Bulls way the following year when they swept the Bad Boys away for good in the conference finals on the way to the franchise’s first title. As it turned out, as mean as the the Pistons were, they would just be the needed hurdle that helped strengthen the dominant, six-championship winning team of the 1990s.

1) Chicago Bulls @ New York Knicks — Eastern Conference Second Round, Game 5 (May 18, 1994)

After Michael Jordan’s retirement, not many experts gave the Bulls a chance to win a fourth straight title, many even wondered if they could make the playoffs with Scottie Pippen at the lead. Pippen proved doubter after doubter wrong as the Bulls won 55 games in the regular season and secured the No. 3 seed in the East. On the opposite bench, the Knicks were looking at their best chance under coach Pat Riley to become champions without Jordan able to play a role in their playoff fortunes.

These two hated rivals met for the third straight year in the playoffs and their best of seven series started with a 2-2 tie with both teams winning their home games. Game 5 came up at Madison Square Garden in the classic, series-hinging position and both teams played incredibly even down to the final seconds.

It was an epic contest that saw the Bulls grab hold of the lead late in regulation courtesy of a B.J. Armstrong jumper, but the tide turned in controversial fashion. With seconds remaining, Knicks guard Hubert Davis attempted a 3-point shot to give the Knicks the lead; Pippen defended the shot perfectly but referee Hue Hollins decided to call a foul on Pippen to give Davis two free throws, which he nailed to give the Knicks the lead and the 87-86 win. After three years of unqualified success, many Bulls fans came of age in this moment and learned just what disappointment was like, it was literally unbelievable that a foul was called there and such an important game was taken away for no reason.

Tom Cruze/Chicago Sun-Times The phantom foul which f-ed up Chicago: Scottie Pippen legally defending Hubert Davis during the closing seconds of Game 5 of the 1994 Eastern Conference semifinals.

Tom Cruze/Chicago Sun-Times
The phantom foul which f-ed up Chicago: Scottie Pippen legally defending Hubert Davis during the closing seconds of Game 5 of the 1994 Eastern Conference semifinals.

New York went on to defeat the Bulls in seven games, the only time it got the better of Chicago in their series of tense playoff series in the 1990s.  After Game 7 concluded, I cried like a baby not just because the Bulls lost but for what could have been, what Bulls fans knew would have been, if the Bulls won Game 5. The Knicks went on to knock off Indiana in the conference finals and played out the NBA Finals in seven, losing to the Houston Rockets.

I will go to my deathbed believing that the Bulls would have defeated the Indiana Pacers and played the Rockets in the NBA Finals if they won that Game 5. There stood a chance for the Bulls to win the NBA title in 1994, one of the most unexpected results in basketball history in the wake of Jordan’s retirement was erased by one boneheaded foul call. Pippen had a MVP-type season, in many ways his greatest season, but it stands forever incomplete.

Well…that was a tough walk down memory lane, but still I hoped that you enjoyed my list.  Yes, it was filled of anguish and pain but also full of memories, in the cases of the Hawks and Bulls losses you can even argue that the losses were instrumental in leading the franchises to eventual titles down the line. With pain there comes opportunities for redemption and in Chicago sports you learn early there is always room for both.

Follow Regal Radio on Twitter @regalradio1 and on Facebook under Regal Radio; follow Sidney on Twitter @sidkid8

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One response to “Sid Ranks Em’ All: Top 5 Toughest Losses in Chicago Sports

  1. Pingback: Sid Ranks Em’ All: Best Chicago Bears Week 1 Wins | WARR - We Are Regal Radio·

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