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30-Day Challenge: My most painful Bears memory — Super Bowl XLI

Super Bowl XLI - Indianapolis Colts vs Chicago Bears Photo by Steve Grayson/Getty Images

Kelvin Hayden scampered down the sideline and my nightmares came true.

All around me, my friends and family were groaning and pleading and crying for his capture at the hands of desperate Bears defenders. But I was silent. On my knees, silent. Eyes affixed, silent. We knew these runbacks. Since the team hired Lovie Smith two season prior, we’d returned 10 interceptions and three fumbles for touchdowns. You always look for the linemen. Once your man is passing the linemen and the receivers and running backs are blocked, you’ve got six.

At the 20, I could tell that Muhsin Muhammad — the intended receiver on the play — was not going to catch Hayden. The rest of the Bears in view of Hayden were linemen. He dove and rolled into the endzone. I put 10 fingers in the air.

A few hours earlier, it was a fist. Devin Hester had returned the opening kickoff of Super Bowl XLI for a touchdown, and while my friends and family around me stood and screamed and cheered and Arsenio’d, I stayed quiet. Raised my fist in the air. Nodded. Said, “Okay, let’s get started.” I’d predicted Devin would get one. I felt no surprise nor now great thrill when he did. My expectation was a dogfight, ruled by our greatness, yielding victory. Had Alex Brown as my game MVP. Hester was the appetizer. This was to be the greatest night of my sports fan life.

For a while, it was. We led 7-0 on the Hester touchdown and 14-6 at the end of the 1st quarter. We didn’t fall behind until late in the 2nd quarter and went to the locker room down 16-14. I spent halftime pacing up and down the building’s stairwell, wearing a white headband on which I’d written “GROSSMAN” in Sharpie. Missed Prince’s performance. We trailed by five at the end of the 3rd. Not great, but still right there.

The Hayden return was where my heart stopped. As a Super Bowl historian, I was all too aware of the foreboding stat of the day: the greatest deficit overcome in a Super Bowl was ten points. As Hayden ran back the pick, I just kept hoping we would tackle him. Up five, we could hold the Colts to a field goal and tie the game with a touchdown and two-point conversion.

A touchdown, though, meant a 12-point lead midway through the fourth. If he scores, my brain kept running, we’re in a two-possession game and a battle with the gods.

Sure enough, the first words out of Jim Nantz’s mouth after the extra point: “No team in Super Bowl history has ever come back from a margin larger than 10 points down.”

The game wasn’t over — we had more than 11 minutes remaining — but I felt crushed in a way I never had before as a fan. Eleven minutes and change of game time later, that feeling was all I had left.


The question for today’s 30-day challenge is as simple as it is devastating: Write about your most painful Bears memory. Considering I was four years old in January of 1986, Super Bowl XLI was MY Super Bowl. That was the game that was going to define me as a Bears fan.

Unfortunately, it did. There is no other choice for most painful Bears memory. Every now and again during the season, a fan will drop a poll asking for the most painful recent moment in Bears history, and the NFC championship scores pretty high. I even see ones where the Double Doink finishes first. To each their own, I guess, but there is nothing like the Super Bowl. If you’re a generation ahead of me, you’re probably a tad too young to have felt the impact of the 1956 NFL championship game, AKA Sneakers Game: Frugality’s Revenge.

In fact, on the all-time Bears heartbreak list, Super Bowl XLI ranks high no matter how you cut it, and will take its place with 1956, 1942, 1934 (AKA Sneakers Game: A New Hope) — and, if you are literally George Halas.

So no, not only is this not a question for me from a Bears fan perspective, but it’s not a question for me from a Chicago sports fan perspective. Super Bowl XLI is my most painful sports memory, period. Thinking about it now feels like if the Bulls never got past the Pistons. That’s the best comparison.

My other most painful moments are the 2003 and 2008 Cubs. I needed 2016 to wipe those off the books. But at least those are series, and at least neither was in the World Series. What if the Cubs had lost the 2016 World Series the way Cleveland did — would that be worse than Super Bowl XLI? I ask myself that all the time. I think the answer is no. First of all, I still felt like the 2016 Cubs were a year ahead of schedule, which made a possible loss bearable — and boy, down 3-1, I thought that was coming. The 2006 Bears were ripe.

Second, the unique spotlight of the Super Bowl dominates anything else. Game 7 of the 2016 World Series is one of the greatest sporting events I’ve ever seen, while Super Bowl XLI is a relatively run-of-the-mill Super Bowl. Here are their ratings and total viewerships:

The Super Bowl is singular: There is no other experience in American sports akin to knowing that 140 million other people watched your favorite team endure their greatest professional heartbreak.

Third, in Chicago, the Super Bowl was all hands on deck, because the Bears belong to all of us. If we lost Game 7 of the 2016 World Series, “we” would just be half of us. The other half won their title 11 years prior. My Sox fan friends were great to me after we won, a result perhaps of my having been great to them in 2005. Yet there is still that divide.

When the ‘85 Bears won, we all won.

When the ‘06 Bears lost, we did that together too. The pain hit harder.

And we weren’t even on the team.


In the years since Super Bowl XLI, I’ve had the chance to get to know a number of players from that fabulous team. To a man, they all talk about the anguish of losing that Super Bowl. Some are more upbeat than others, some more downtrodden, but for each of them, the game stands as a point of no return.

Thomas Jones watched every Super Bowl of his life until XLI and hasn’t watched one since, calling it a pain “that will never leave.” Olin Kreutz acknowledges that while football has given him and his family everything, the Super Bowl was “the worst game in the world to lose.” Charles Tillman said that while he didn’t have any regrets because he gave it everything he had, losing the Super Bowl left him “sick to my stomach.”

“I cried after the game,” Tillman told me in 2016. “I sat in the locker room and I cried. I was disappointed in the outcome. It wasn’t what I envisioned.”

These guys and the rest of that team are champions in my book, and I know that they know the greatness that they accomplished together. But they don’t have that final piece. Instead, they have a hollow space that will last forever.

“It does something to you emotionally — it’s like a girlfriend you never really got over,” Thomas shared with me in 2016. The NFC championship game was “a kid’s dream,” he said. “And then two weeks later, the worst feeling of your football career. A two-week swing. The best feeling ever in your football career to the worst.”

After that game, I had to write a column just to temporarily and marginally shake free of the weight of that loss. Now, a decade and a half later, I keep those guys in mind when I think about XLI. No matter how bad it was for us, we will never understand how bad it was for them. That’s what I remind myself.

And then I am shattered by the flip side. If we can’t understand what they feel, then what they feel must be unbearable. Because boy oh boy, it was for us.

Jack M Silverstein is Chicago’s sports historian, Bears historian at Windy City Gridiron, and author of the forthcoming “6 Rings: The Bulls, The City, and the Dynasty that Changed the Game.” His newsletter, “A Shot on Ehlo,” brings readers inside the making of the book, with original interviews, research and essays. Sign up now, and say hey at @readjack.

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What was your most painful Bears memory? Drop a comment and let’s help each other. #BearDown