Sometimes we get an idea or two from the lively commenting section right here at The Big Lead, and that’s exactly where the thought sprouted for this somewhat pain-inducing post.

A little over a week ago I wrote about the Blue Jays new uniforms and like clockwork, Joe Carter’s walkoff homer in Game 7 of the World Series against the Phillies inevitably came into conversation, which promptly unearthed distinct, familiar pain to some of our readers who live and die with the Philadelphia Phillies. While I could clearly care less about the Phillies, I couldn’t help but think of the most gut-wrenching sports moment I’ve experienced as a fan, as well as for my fellow TBL compadres. So each of us has decided to share our worst moments. Feel free to share yours in the comments, or you can just revel in our misery.

1990 NFC Championship – New York Giants at San Francisco 49ers
Final Score: Giants 15, Niners 13
Gut-Wrenched: Tim Ryan
This was by far the worst loss I’ve ever experienced as a sports fan. Growing up, no team mattered to me more than the San Francisco 49ers. I was obsessed with the greatness of Jerry Rice, both on the field and in Tecmo Bowl, and I was dumbfounded by the hits Ronnie Lott would deliver on a weekly basis. It quickly became an obsession. I collected all of the issues of Sports Illustrated that involved 49er greatness and placed them in large zip-lock bags to maintain their sublime condition.

All of my friends were of course New York Giant fans and my older brother happened to be an insufferable Cowboys fan. I was surrounded by assholes. So going into that NFC Championship game, the idea of the Niners taking out Parcells, the great LT, Jeff freaking Hostetler and the rest of the hated Giants to advance to their fifth Super Bowl (at the time) and unprecedented three-peat felt like sure destiny. Sadly, ’twas not to be. And it wasn’t so much the fact that San Francisco lost the game, but the manner in which it happened.

A few moments stick out from this classic game as though it were played last Sunday. First, Parcells and his genius decision to fake punt after noticing Bill Romanowski was sitting out a play to rest his knee. His absence on the field left a giant gap open right up the gut for Gary Reasons to run through, and he did. Within seconds, the returner on the play, John Taylor, was the only one left to prevent Reasons from taking it all the way in, and he managed to do so, but not before Reasons famously pointed directly at Taylor as he trucked down the field. Just unforgettable. Looking back, I love what Reasons did as much as I still hate it. The next lasting image, of course, was when Leonard Marshall pummeled Joe Montana from behind as he rolled out right, absolutely crushing the three-time Super Bowl MVP.

More scarring than the hit itself was the moment CBS went to the sideline for an official injury report. The information given to the booth regarding Montana’s physical state was: “everything hurts.” Naturally, my brother found this piece of information endlessly hilarious to the point I was convinced it must have been the funniest thing he had ever heard in his entire life. I was beyond crushed, and even as a little kid, I knew it was all over. No Montana. No three-peat. No nothing. Sure enough, on their next possession following the violent decimation of Montana, Steve Young handed off to Roger Craig, who inexplicably never quite had control of the football, leading to LT sniffing out the loose ball like a seasoned Bloodhound and instantly gobbling it up. Giants ball. Game not officially over, but for all intents and purposes… Game. Over.

2007 – Appalachian State at Michigan
Final Score: Appalachian State 34-32 Michigan
Gut-Wrenched: Tyler Duffy
Michigan had come off an 11-win regular season in 2006, missing the title game through a 42-39 loss at Ohio State. They were ranked in the top five. Henne, Hart and Long were returning as seniors. Eleven starters were eventual NFL Draft Picks. 2007 was the year. The game was on something called “The Big Ten Network.” Comcast did not carry it yet. Michigan fans outside the stadium could not watch it on TV. I was packing for my move to Boston for grad school. I checked the score on my cell phone which had that feature. It was 28-17 at halftime.

I was okay. I’d seen slow, horrendously slow starts from Carr-era Michigan teams. I was firmly confident the Wolverines the wheels would begrudgingly turn in the second half and Michigan would escape with a win, with mild embarrassment and with a wakeup call. Refreshing my phone progressed to following the gamecast on my computer. I sat down at my desk for the final drive, refreshed constantly and saw Michigan was lining up for a field goal. Then…”Appalachian State 34-32 Michigan Final.” I turned to ESPN. I immediately saw this highlight. I couldn’t rouse anger. I couldn’t form words. I just stared.

1995 NCAA Tournament – Missouri vs. #1 UCLA & 1997 College Football – Missouri vs. #1 Nebraska
Final Scores: UCLA 75, Missouri 74; Nebraska 45, Missouri 38 (OT)
Gut-Wrenched: Jason Lisk
This wasn’t easy. Coming of age in Missouri in the late 80′s and 90′s provided me with a top 10 of gut-punch moments, from Missouri’s failures in the NCAA tournament to the Chiefs’ failures in the playoffs. The Fifth Down. Northern Iowa and Maurice Newby. The Lin Elliott game against the Colts in the playoffs. These would all be candidates, but I finally settled on two.

When your team loses two heartbreaking games in improbable fashion to the team that goes on to win the National Championship, yeah that’s a different kind of gut-wrenching moment. We weren’t front runners, and we expected the worst, especially after the Fifth Down Game earlier in the decade. And boy did fate deliver.

The Missouri-UCLA game was during my Junior year of college. Missouri had been a #1 seed the year before and had gone undefeated in the Big 8, but expectations were lower in 1995. The team was young and inexperienced. When we left campus for Spring Break right before the bracket was set, there was little expectation that they would do well. Then, they beat Indiana and Bobby Knight, setting up a game against #1 UCLA. All game long, Missouri played hard and the game went back and forth. When Julian Winfield hit a jumper from the top of the lane with 4.8 seconds, I leaped with joy. This tournament, that had been so cruel to Missouri over the last decade as a higher seed, was finally going the other way.

But 4.8 seconds is a long time in basketball.

Missouri football was so bad for much of my youth. I worked for the football team in college, filming games, so I had a first hand view of the hard work and lack of success. I was in College Station when they lost 73-0, and I was in Illinois when they picked up 1 first down in a 41-0 defeat. And more than anything, I watched us lose in non-competitive fashion year after year to Nebraska. In 1997, I had since graduated, and the team was finally coming together behind a transcendent quarterback, Corby Jones. But there was still big, bad Nebraska, who Missouri had not defeated since I was four years old. The Cornhuskers came into the game #1, and as a 28-point favorite. It was a gray day, and Brent Musberger was on the call. It was a big game, and there was a buzz despite the long odds.

Then, Missouri went out and played the game of their lives. Corby Jones was amazing. Missouri took a 38-31 lead late in the fourth quarter, and the impossible seemed real. I was watching in Kansas City, and I was on the phone with friends in St. Louis. We were planning to meet in Columbia and be part of the celebration and the evening that we waited for throughout our college days.

Nebraska got the ball back, 1 minute left, down 7, at their own 33. They had no timeouts. This was the situation you wanted them in, a team that was not great at passing, always relied on pounding teams and getting a lead, having to hurry up. But Nebraska got the ball to the Missouri 12 with a few seconds remaining. They still needed a miracle. And they got it, when Scott Frost’s pass to Shevin Wiggins was knocked out, but then he kicked it over his head (illegally) and into the diving arms of Matt Davison.

1993 Final Four – Michigan Wolverines vs North Carolina Tar Heels
Final Score: UNC 77, Michigan 71
Gut-Wrenched: Stephen Douglas
I was 10-years-old when Chris Webber spun around and called timeout against North Carolina. It was the perfect storm at the time. I was young and just beginning my intense sports-fandom. It was just unbelievable. And the worst part was that I was listening to the end of the game on a radio because my parents made me go to bed. It was probably the first time that sports meant something personal to me. Amazingly, the first time that politics ever meant something to me had come the previous fall when I started rooting for Ross Perot. Don’t ask me why. I must have found him amusing as as child. When results started coming in on election night I was heartbroken to hear that my favorite political player had lost. Unfortunately, that didn’t prepare me for Michigan’s loss. In just a few short months I vowed never to take sports or politics seriously ever again.

1994, Dolphins at Jets, Nov. 27
Get-wrenched: Jason McIntyre
My favorite baseball team sucked during my childhood (Yankees). My favorite basketball team was awesome (Lakers), so the memories were many. The Jets were mostly awful, and I was too young to really enjoy the 1986 playoff season. But when I was in high school, the Jets appeared to be headed back to the playoffs in 1994. They had just beaten a pretty good Warren Moon-led Vikings team, and rival Dan Marino was coming to town. The Jets were 6-5 and a win would position them to get into the postseason. The Jets grabbed a 24-6 lead in the third quarter on a Johnny Mitchell (Nebraska!) TD catch. I couldn’t have been more excited. I was getting ready to order a Rob Moore jersey and he was quickly becoming my favorite player on the team, replacing former stars Al Toon and Wesley Walker.

Then, Boomer Esiason imploded (two picks, three fumbles). Then, Rob Moore suffered a concussion. Then, Dan Marino happened.

Marino threw two TD passes to Mark Ingram and the Dolphins drew within 24-21. Marino got the ball back with 2:34 and drove 84 yards as if he were playing pitch-and-catch in his yard with the neighborhood kids. In the waning seconds, there was hope the Dolphins would have to settle for a FG and overtime. But Marino memorably called for a spike to kill the clock, and the Jets’ defenders completely bit. Marino threw a quick pass to Ingram for a TD and the Jets lost, 28-24.

This game is the reason the Dolphins are still one of my least-favorite teams in the NFL (Patriots and the Giants, too). The Jets, amazingly, didn’t win a game the rest of the season and finished 6-10. Coach Pete Carroll was booted. Rich Kotite came in. It didn’t matter. The Jets went 3-13 in 1995. The Jets went 1-15 in 1996. So basically, the Marino fake spike TD pass was one that the Jets didn’t recover from for years (lost 28 of their next 32 games).

[Photo via Getty]